{"jobs":[{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4721252005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448078005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4721252005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"375","title":"Analytics Engineer, Data","company_name":"Tailscale","first_published":"2026-08-04T14:21:41-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are looking for an Analytics Engineer who thrives in high-complexity environments—someone excited to bring clarity to chaos, untangle complex models, and lay down the foundation for scalable solutions.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a hands-on, high-impact role for someone who isn’t afraid to address manual processes, viewing them as opportunities to build scalable solutions that drive meaningful impact. You’ll work closely with stakeholders across the company to build reliable, trusted data models that support reporting, analysis, and decision-making.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Dive into complex systems and manual workflows to develop an understanding of our tools and constraints.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Thoughtfully design and maintain clean, scalable, production-grade dbt models (e.g., ARR, revenue recognition).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work across the full data pipeline, from ingestion to transformation to visualization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take a pragmatic approach to system challenges, balancing quick fixes with thoughtful long-term design.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with Finance, Engineering, Sales, and other teams across the company to understand data needs and deliver timely, practical solutions.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience designing and maintaining production-grade data models and pipelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of modern data modeling principles and best practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong SQL skills and confidence working with complex datasets and schemas.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High attention to detail, with high standards for data accuracy and validation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility and resourcefulness in navigating manual tasks or imperfect systems.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Passion for clean code, scalable architecture, and incrementally reducing complexity over time.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage time, prioritize effectively, and thrive in a fast-moving environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear communication skills with both technical and non-technical collaborators.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Willingness to flexibly support other domains (e.g., Product, Marketing, and Engineering) as the team grows.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience at a high-growth PLG SaaS company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of transforming manual, ad hoc workflows into scalable data pipelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with billing systems, GAAP accounting, revenue recognition, or audit support.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exposure to Stripe, Salesforce, or Orb in billing and finance contexts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with financial cycles and the need for fast iteration during month- and quarter-end.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Our Tech Stack\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Snowflake, dbt, Hightouch, Fivetran, Looker, Stripe, Salesforce, Orb.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$203,680\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$254,600 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4130234005,"name":"Data","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4721289005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448078005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4721289005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"375","title":"Analytics Engineer, Data","company_name":"Tailscale","first_published":"2026-08-04T14:21:42-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are looking for an Analytics Engineer who thrives in high-complexity environments—someone excited to bring clarity to chaos, untangle complex models, and lay down the foundation for scalable solutions.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a hands-on, high-impact role for someone who isn’t afraid to address manual processes, viewing them as opportunities to build scalable solutions that drive meaningful impact. You’ll work closely with stakeholders across the company to build reliable, trusted data models that support reporting, analysis, and decision-making.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Dive into complex systems and manual workflows to develop an understanding of our tools and constraints.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Thoughtfully design and maintain clean, scalable, production-grade dbt models (e.g., ARR, revenue recognition).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work across the full data pipeline, from ingestion to transformation to visualization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take a pragmatic approach to system challenges, balancing quick fixes with thoughtful long-term design.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with Finance, Engineering, Sales, and other teams across the company to understand data needs and deliver timely, practical solutions.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience designing and maintaining production-grade data models and pipelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of modern data modeling principles and best practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong SQL skills and confidence working with complex datasets and schemas.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High attention to detail, with high standards for data accuracy and validation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility and resourcefulness in navigating manual tasks or imperfect systems.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Passion for clean code, scalable architecture, and incrementally reducing complexity over time.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage time, prioritize effectively, and thrive in a fast-moving environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear communication skills with both technical and non-technical collaborators.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Willingness to flexibly support other domains (e.g., Product, Marketing, and Engineering) as the team grows.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience at a high-growth PLG SaaS company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of transforming manual, ad hoc workflows into scalable data pipelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with billing systems, GAAP accounting, revenue recognition, or audit support.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exposure to Stripe, Salesforce, or Orb in billing and finance contexts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with financial cycles and the need for fast iteration during month- and quarter-end.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Our Tech Stack\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Snowflake, dbt, Hightouch, Fivetran, Looker, Stripe, Salesforce, Orb.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$152,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$190,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4130234005,"name":"Data","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4723940005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449446005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4723940005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"386","title":"Brand Designer","company_name":"Tailscale","first_published":"2026-08-19T14:53:03-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for an experienced Brand Designer to help bring our brand to life across every customer touchpoint. You\u0026#39;ll create thoughtful, high-quality creative that helps people understand our products, builds trust with technical audiences, and supports some of our most important marketing initiatives.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role reports to the Team Lead and partners closely with Brand, Growth, Web, Content, Product Marketing, and Developer Relations. You\u0026#39;ll own projects from concept through execution, contribute to the evolution of our design systems, and help us scale creative output without sacrificing quality.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re looking for someone who cares deeply about craft, thrives in collaborative environments but is able to work autonomously while requiring minimal direction, and enjoys solving complex communication problems through thoughtful design.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own brand design projects from creative brief through final delivery with limited guidance\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design high-quality creative assets across web, campaigns, events, social media, presentations, product marketing, and internal communications\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Apply and thoughtfully extend Tailscale\u0026#39;s visual identity across new formats and channels\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create reusable templates, design systems, and creative processes that improve consistency and efficiency\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner closely with Growth, Web, Product Marketing, Content, and Developer Relations to deliver cohesive customer experiences\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Present design concepts and rationale to stakeholders and thoughtfully incorporate feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Balance multiple projects while consistently delivering polished, production-ready work\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute ideas that improve the quality, scalability, and effectiveness of our creative work\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;3+ years of professional experience in brand, marketing, or visual design\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong portfolio demonstrating exceptional design foundations: color theory, accessibility, typography, layout, and storytelling\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Fluency in Figma and Adobe Creative Cloud\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience designing for digital marketing, websites, campaigns, and brand systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of production-ready design across digital and print\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and presentation skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage multiple projects and priorities with minimal oversight\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating cross-functionally with marketers, writers, developers, and other designers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong attention to detail with a high bar for quality and consistency\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable giving and receiving constructive design feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Actively seeks opportunities to refine processes, improve project organization, and make collaboration more effective through thoughtful recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Curious by nature, with a desire to learn about the technical world of networking.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience designing for B2B SaaS or developer-focused products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with design systems and component libraries\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Motion design or animation experience\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Illustration or icon design experience\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Basic understanding of HTML/CSS and web design constraints\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting experimentation, conversion optimization, or growth marketing initiatives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in fast-paced startup or scale-up environments\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience art-directing or mentoring junior designers\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$163,480\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$205,020 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4723980005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449446005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4723980005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"386","title":"Brand Designer","company_name":"Tailscale","first_published":"2026-08-19T14:53:04-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for an experienced Brand Designer to help bring our brand to life across every customer touchpoint. You\u0026#39;ll create thoughtful, high-quality creative that helps people understand our products, builds trust with technical audiences, and supports some of our most important marketing initiatives.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role reports to the Team Lead and partners closely with Brand, Growth, Web, Content, Product Marketing, and Developer Relations. You\u0026#39;ll own projects from concept through execution, contribute to the evolution of our design systems, and help us scale creative output without sacrificing quality.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re looking for someone who cares deeply about craft, thrives in collaborative environments but is able to work autonomously while requiring minimal direction, and enjoys solving complex communication problems through thoughtful design.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own brand design projects from creative brief through final delivery with limited guidance\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design high-quality creative assets across web, campaigns, events, social media, presentations, product marketing, and internal communications\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Apply and thoughtfully extend Tailscale\u0026#39;s visual identity across new formats and channels\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create reusable templates, design systems, and creative processes that improve consistency and efficiency\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner closely with Growth, Web, Product Marketing, Content, and Developer Relations to deliver cohesive customer experiences\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Present design concepts and rationale to stakeholders and thoughtfully incorporate feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Balance multiple projects while consistently delivering polished, production-ready work\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute ideas that improve the quality, scalability, and effectiveness of our creative work\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;3+ years of professional experience in brand, marketing, or visual design\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong portfolio demonstrating exceptional design foundations: color theory, accessibility, typography, layout, and storytelling\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Fluency in Figma and Adobe Creative Cloud\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience designing for digital marketing, websites, campaigns, and brand systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of production-ready design across digital and print\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and presentation skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage multiple projects and priorities with minimal oversight\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating cross-functionally with marketers, writers, developers, and other designers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong attention to detail with a high bar for quality and consistency\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable giving and receiving constructive design feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Actively seeks opportunities to refine processes, improve project organization, and make collaboration more effective through thoughtful recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Curious by nature, with a desire to learn about the technical world of networking.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience designing for B2B SaaS or developer-focused products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with design systems and component libraries\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Motion design or animation experience\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Illustration or icon design experience\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Basic understanding of HTML/CSS and web design constraints\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting experimentation, conversion optimization, or growth marketing initiatives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in fast-paced startup or scale-up environments\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience art-directing or mentoring junior designers\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$117,750\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$153,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4735278005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454816005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4735278005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"426","title":"Commercial Legal Counsel","company_name":"Tailscale","first_published":"2026-09-18T09:40:40-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are hiring a Commercial Legal Counsel to lead day-to-day commercial legal support as Tailscale continues to grow. You will partner closely with Sales, Partnerships, Finance, Security, Product, and Operations to help the company close business, manage risk, and build contracting practices that scale.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role reports to the Head of Legal. The strongest candidate may be an experienced commercial counsel ready for broader ownership, a senior counsel who has led complex transactions and programs, or a commercial legal leader who can shape the function while remaining hands-on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate legal issues into clear options and recommendations that help teams make timely decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support international transactions and coordinate with outside counsel when local or specialized expertise is needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to other legal priorities as the company and legal function evolve.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Meaningful experience advising technology companies on commercial transactions, including in-house experience or equivalent experience working closely with technology clients.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong judgment and the ability to distinguish material business risk from issues that can be addressed through practical guardrails.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear, concise communication and the ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort working independently, prioritizing competing demands, and making progress with incomplete information.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, software as a service, or open-source products.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or application programming interfaces.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privacy, data protection, security, artificial intelligence, intellectual property, or product counseling issues that arise in technology transactions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting global customers or coordinating advice across multiple jurisdictions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience selecting or implementing contract lifecycle management tools, workflow automation, or commercial legal metrics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience mentoring colleagues or helping define the structure and priorities of a growing commercial legal capability.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$187,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$234,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044818005,"name":"Office of the CEO","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4734427005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454816005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4734427005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"426","title":"Commercial Legal Counsel","company_name":"Tailscale","first_published":"2026-09-18T09:40:38-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are hiring a Commercial Legal Counsel to lead day-to-day commercial legal support as Tailscale continues to grow. You will partner closely with Sales, Partnerships, Finance, Security, Product, and Operations to help the company close business, manage risk, and build contracting practices that scale.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role reports to the Head of Legal. The strongest candidate may be an experienced commercial counsel ready for broader ownership, a senior counsel who has led complex transactions and programs, or a commercial legal leader who can shape the function while remaining hands-on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate legal issues into clear options and recommendations that help teams make timely decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support international transactions and coordinate with outside counsel when local or specialized expertise is needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to other legal priorities as the company and legal function evolve.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Meaningful experience advising technology companies on commercial transactions, including in-house experience or equivalent experience working closely with technology clients.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong judgment and the ability to distinguish material business risk from issues that can be addressed through practical guardrails.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear, concise communication and the ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort working independently, prioritizing competing demands, and making progress with incomplete information.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, software as a service, or open-source products.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or application programming interfaces.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privacy, data protection, security, artificial intelligence, intellectual property, or product counseling issues that arise in technology transactions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting global customers or coordinating advice across multiple jurisdictions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience selecting or implementing contract lifecycle management tools, workflow automation, or commercial legal metrics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience mentoring colleagues or helping define the structure and priorities of a growing commercial legal capability.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$250,580\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$313,560 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044818005,"name":"Office of the CEO","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4740468005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449549005,"location":{"name":"Hybrid (Vancouver, British Columbia)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4740468005,"updated_at":"2026-10-05T12:35:44-04:00","requisition_id":"EVG-CAE-TOR/VAN","title":"Customer Account Executive ","company_name":"Tailscale","first_published":"2026-10-05T12:22:53-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Up to 1 year of quota-carrying or closing experience, in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup in a fully remote role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages,\u0026amp;nbsp; coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Vancouver and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$167,500\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$167,500 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053580005,"name":"Hybrid (Toronto)","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null},{"id":4053186005,"name":"Hybrid (Vancouver)","location":"Vancouver, British Columbia, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4715169005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4445032005,"location":{"name":"Hybrid (Denver, Colorado, United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4715169005,"updated_at":"2026-10-05T12:12:25-04:00","requisition_id":"EVG-CAE","title":"Customer Account Executive ","company_name":"Tailscale","first_published":"2026-07-14T14:31:08-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Up to 1 year of quota-carrying or closing experience, in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup in a fully remote role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages,\u0026amp;nbsp; coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Denver and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$100,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$125,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053187005,"name":"Hybrid (Denver)","location":"Denver, Colorado, United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724118005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449549005,"location":{"name":"Hybrid (Toronto, Ontario)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724118005,"updated_at":"2026-10-05T12:35:44-04:00","requisition_id":"EVG-CAE-TOR/VAN","title":"Customer Account Executive ","company_name":"Tailscale","first_published":"2026-09-15T16:18:01-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Up to 1 year of quota-carrying or closing experience, in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup in a fully remote role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages,\u0026amp;nbsp; coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Toronto and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$167,500\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$167,500 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053580005,"name":"Hybrid (Toronto)","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null},{"id":4053186005,"name":"Hybrid (Vancouver)","location":"Vancouver, British Columbia, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4715160005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4445021005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4715160005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SrCSUP-NAMER","title":"Customer Reliability Engineer","company_name":"Tailscale","first_published":"2026-07-14T15:14:01-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;If you\u0026#39;re passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We\u0026#39;re seeking a motivated Customer Reliability Engineer to join our team. You\u0026#39;ll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Reliability Engineer, you\u0026#39;ll partner closely with the Customer Success Team, Support Team, and Product/Engineering to close the gap between \u0026quot;customer has described a problem\u0026quot; and \u0026quot;engineering has what it needs to fix it.\u0026quot; This role reports directly to the Customer Reliability Engineer Team Lead.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Get on calls with customers, pull logs, and communicate with the customer about leading theories.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what\u0026#39;s already been ruled out, and a proposed engineering team to own the fix.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Support, CSE, and Product/Eng, while staying within this team\u0026#39;s scope.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with programming/scripting in Go, Python, JSON\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with packet-level analysis\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$115,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$144,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4039044005,"name":"Customer Support","child_ids":[4134423005],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4715148005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4445021005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4715148005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SrCSUP-NAMER","title":"Customer Reliability Engineer","company_name":"Tailscale","first_published":"2026-07-14T15:14:00-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;If you\u0026#39;re passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We\u0026#39;re seeking a motivated Customer Reliability Engineer to join our team. You\u0026#39;ll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Reliability Engineer, you\u0026#39;ll partner closely with the Customer Success Team, Support Team, and Product/Engineering to close the gap between \u0026quot;customer has described a problem\u0026quot; and \u0026quot;engineering has what it needs to fix it.\u0026quot; This role reports directly to the Customer Reliability Engineer Team Lead.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Get on calls with customers, pull logs, and communicate with the customer about leading theories.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what\u0026#39;s already been ruled out, and a proposed engineering team to own the fix.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Support, CSE, and Product/Eng, while staying within this team\u0026#39;s scope.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with programming/scripting in Go, Python, JSON\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with packet-level analysis\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$154,100\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$192,960 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4039044005,"name":"Customer Support","child_ids":[4134423005],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724307005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449639005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724307005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-JrCSUP-NAMER","title":"Customer Support Engineer (Tier 1)","company_name":"Tailscale","first_published":"2026-08-19T11:21:21-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated \u0026lt;strong\u0026gt;Support Engineer (Tier 1)\u0026lt;/strong\u0026gt; to join our growing team of support professionals. You will serve as the face of the company for a large portion of our community, handling a broad range of tickets that will help flex your technical muscles.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Tier 1 engineer, you’ll be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Tier 1 Support Team Lead and will play a key role in our journey.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Act as the primary technical resource for less complex issues, resolving a wide range of configuration and networking challenges to keep them unblocked.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$84,420\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$132,660 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4039044005,"name":"Customer Support","child_ids":[4134423005],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724309005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449639005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724309005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-JrCSUP-NAMER","title":"Customer Support Engineer (Tier 1)","company_name":"Tailscale","first_published":"2026-08-19T11:21:22-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated \u0026lt;strong\u0026gt;Support Engineer (Tier 1)\u0026lt;/strong\u0026gt; to join our growing team of support professionals. You will serve as the face of the company for a large portion of our community, handling a broad range of tickets that will help flex your technical muscles.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Tier 1 engineer, you’ll be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Tier 1 Support Team Lead and will play a key role in our journey.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Act as the primary technical resource for less complex issues, resolving a wide range of configuration and networking challenges to keep them unblocked.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$63,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$99,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4039044005,"name":"Customer Support","child_ids":[4134423005],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724314005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449643005,"location":{"name":"Remote (United Kingdom)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724314005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-JrCSUP-UK","title":"Customer Support Engineer (Tier 1)","company_name":"Tailscale","first_published":"2026-08-19T11:42:16-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated \u0026lt;strong\u0026gt;Support Engineer (Tier 1)\u0026lt;/strong\u0026gt; to join our growing team of support professionals. You will serve as the face of the company for a large portion of our community, handling a broad range of tickets that will help flex your technical muscles.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Tier 1 engineer, you’ll be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Tier 1 Support Team Lead and will play a key role in our journey.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Act as the primary technical resource for less complex issues, resolving a wide range of configuration and networking challenges to keep them unblocked.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;UK Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;£49,770\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;£78,210 GBP\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4039044005,"name":"Customer Support","child_ids":[4134423005],"parent_id":null}],"offices":[{"id":4015351005,"name":"Remote (United Kingdom)","location":"United Kingdom","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4726020005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4450466005,"location":{"name":"Remote (Singapore)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4726020005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"392","title":"Director, APAC Go-to-Market","company_name":"Tailscale","first_published":"2026-08-31T19:51:26-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for a Director, APAC Go-to-Market to build and lead our GTM business in Asia Pacific, starting from Singapore.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;APAC represents an important growth opportunity for Tailscale. We have strong conviction in the region and are looking for a leader who can turn that opportunity into a meaningful, durable business: building pipeline and revenue, developing a strong partner ecosystem, winning strategic customers, and building the team we need to scale.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are looking for someone who has built a region before and wants to do it again from scratch. You will set the APAC go-to-market strategy, determine where and how we invest, recruit and lead our initial regional team, and be directly accountable for commercial results. You will have significant autonomy to determine what Tailscale needs to win in the region.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You will also be a hands-on commercial leader. You’ll spend time with customers and partners, help shape and close our most important opportunities, and develop a deep understanding of how technology companies need to go to market differently across APAC. You’ll bring those insights back to our global Sales, Marketing, Product, and Engineering teams and help Tailscale become a truly global company.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;In this role, you will be able to hire the team you need to succeed. We suspect that will include Sales Development, Account Executives, Solutions Engineering, Customer Engineering, and Partner Marketing, but ultimately we will be open to your recommendation based on expertise. These hires will report directly to you with dotted lines to functional departments in North America and EMEA. You’ll lead that team as a region, while working closely with their functional counterparts elsewhere at Tailscale. This role will report to Tailscale’s President, Kevin Kotecki.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Own the APAC number. \u0026lt;/strong\u0026gt;You will be accountable for regional pipeline creation and revenue growth. Establish clear targets, build the plan to reach them, maintain strong forecasting and pipeline discipline, and continuously adjust our approach based on what the data and the market tell us.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Build and execute Tailscale’s APAC go-to-market strategy.\u0026lt;/strong\u0026gt; Determine which markets, customer segments, use cases, and routes to market offer the greatest opportunity for Tailscale. Translate global company strategy into a focused regional plan while recognizing that what works in North America or Europe will not always work in APAC.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Build a high-performing regional GTM organization.\u0026lt;/strong\u0026gt; Recruit, lead, and develop exceptional sellers and other customer-facing talent in the region. Build a team that operates as one APAC organization while remaining tightly connected to its global functional counterparts. Create the culture, operating rhythms, and accountability required for a small regional team to move quickly and perform at a high level.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lead from the front with customers.\u0026lt;/strong\u0026gt; Personally engage in Tailscale’s most important opportunities in the region. Build relationships with senior technical and business leaders, help the team navigate complex enterprise sales cycles, and serve as executive sponsor for strategic customers. Stay close enough to the market to know why we are winning, why we are losing, and what needs to change.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Build Tailscale’s presence in the region.\u0026lt;/strong\u0026gt; Establish Tailscale as a credible and increasingly visible technology company in APAC. Represent Tailscale with customers, partners, at industry events, and within the broader technology ecosystem. Develop the relationships and market intelligence that allow us to identify opportunities earlier than we otherwise would.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Be the voice of APAC inside Tailscale.\u0026lt;/strong\u0026gt; Build a strong point of view on regional customers, competitors, partners, buying behavior, and market dynamics. Bring that perspective into company decisions about product, packaging, marketing, partnerships, and future investments.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Build the region for the long term.\u0026lt;/strong\u0026gt; We expect the shape of our APAC organization to evolve considerably. Identify what capabilities and investments we need next, make thoughtful resource tradeoffs, and build systems that can scale beyond the first phase of the Singapore office.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Significant experience in enterprise technology go-to-market, with meaningful experience leading Sales or a broader GTM organization across APAC.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have done this before\u0026lt;strong\u0026gt;.\u0026lt;/strong\u0026gt; You have helped build or materially scale an APAC business rather than only operating within an already mature regional organization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A proven track record of owning and exceeding meaningful pipeline and revenue targets in a B2B technology business.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with the APAC technology market and experience operating successfully across multiple countries and cultures, with particularly strong knowledge of Singapore and Southeast Asia.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Established relationships within the regional channel and partner ecosystem, along with a track record of turning those relationships into measurable commercial outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong network of exceptional GTM talent in the region. You know what great sellers and SEs look like and have demonstrated that you can attract them to work with you.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience leading complex enterprise opportunities personally. You are comfortable moving from regional strategy and forecasting into a customer meeting or deal review and materially improving the outcome.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience selling highly technical products to sophisticated buyers. Experience with infrastructure, networking, security, developer tools, cloud, or adjacent enterprise technology is particularly relevant.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong commercial judgment and analytical ability. You understand pipeline mathematics, forecasting, unit economics, market prioritization, and where to invest limited resources to produce the greatest return.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong cross-functional leadership skills. You can lead a regional team while partnering effectively with global Sales, Marketing, Product, Engineering, Customer Success, Finance, and Operations teams that you do not directly manage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication and strong executive presence with customers, partners, candidates, and internal leaders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A builder’s mindset. You are comfortable with ambiguity, limited infrastructure, and changing plans, and you know how to introduce enough process and structure to improve execution without slowing the organization down.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High agency and low ego. You are willing to personally do the work required to establish the region while simultaneously building an organization that will eventually make you less central to every decision.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong perspective on how technology GTM is changing in the age of AI and what those changes mean for winning customers and building partnerships in APAC.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4059190005,"name":"Remote (Singapore)","location":"Singapore","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4735063005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4455090005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4735063005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"427","title":"Enablement Program Specialist, Onboarding","company_name":"Tailscale","first_published":"2026-09-17T17:27:25-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-weight: 400;\u0026quot;\u0026gt;Join our growing Revenue Enablement team, where you\u0026#39;ll own onboarding and the enablement programs that keep our revenue team sharp. You\u0026#39;ll make sure every new customer-facing hire ramps quickly and that ongoing programs deliver real results. From pre-boarding through ramp and into continuous enablement, you\u0026#39;ll design, launch, and run the programs reps rely on by partnering closely with frontline managers and sales leadership, and collaborating across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product.\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones with the potential to lead in person sessions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Extend onboarding into continuous everboarding enablement so reps keep building skills after initial ramp.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design, launch, and manage recurring enablement programs (skill development, product launches, process rollouts, certifications).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable, role-specific enablement paths that support core competencies and career progression.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage the logistics, content, and cadence of programs end to end, keeping them on schedule and on quality.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Instrument programs with metrics (ramp time, completion, competency) and iterate based on data and rep feedback.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage the Tailscale LMS to ensure new-hire materials stay current and accessible.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Explore and pilot AI-driven learning tools (e.g., an AI tutor for asynchronous onboarding).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2–4+ years in revenue/sales enablement, with hands-on program and onboarding ownership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated ability to design, launch, and scale enablement programs in fast-paced, high-growth environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong project management skills and meticulous attention to detail.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written communication and facilitation/instructional-design instincts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong stakeholder management across multiple functions and seniority levels.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Data-driven mindset and comfortable using performance metrics, rep feedback, and tool insights to iterate on programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High degree of ownership and someone who thrives in ambiguity and enjoys building from scratch in a remote-first culture.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: Experience using AI tools to build more efficient and effective learning environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: Prior selling experience, especially to technical personas such as IT, engineering, and security.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$120,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$150,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4735057005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4455090005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4735057005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"427","title":"Enablement Program Specialist, Onboarding","company_name":"Tailscale","first_published":"2026-09-17T17:27:23-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-weight: 400;\u0026quot;\u0026gt;Join our growing Revenue Enablement team, where you\u0026#39;ll own onboarding and the enablement programs that keep our revenue team sharp. You\u0026#39;ll make sure every new customer-facing hire ramps quickly and that ongoing programs deliver real results. From pre-boarding through ramp and into continuous enablement, you\u0026#39;ll design, launch, and run the programs reps rely on by partnering closely with frontline managers and sales leadership, and collaborating across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product.\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones with the potential to lead in person sessions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Extend onboarding into continuous everboarding enablement so reps keep building skills after initial ramp.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design, launch, and manage recurring enablement programs (skill development, product launches, process rollouts, certifications).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable, role-specific enablement paths that support core competencies and career progression.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage the logistics, content, and cadence of programs end to end, keeping them on schedule and on quality.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Instrument programs with metrics (ramp time, completion, competency) and iterate based on data and rep feedback.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage the Tailscale LMS to ensure new-hire materials stay current and accessible.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Explore and pilot AI-driven learning tools (e.g., an AI tutor for asynchronous onboarding).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2–4+ years in revenue/sales enablement, with hands-on program and onboarding ownership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated ability to design, launch, and scale enablement programs in fast-paced, high-growth environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong project management skills and meticulous attention to detail.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written communication and facilitation/instructional-design instincts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong stakeholder management across multiple functions and seniority levels.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Data-driven mindset and comfortable using performance metrics, rep feedback, and tool insights to iterate on programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High degree of ownership and someone who thrives in ambiguity and enjoys building from scratch in a remote-first culture.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: Experience using AI tools to build more efficient and effective learning environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: Prior selling experience, especially to technical personas such as IT, engineering, and security.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$168,800\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4719601005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4447228005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4719601005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"371","title":"Engineering Manager, Control Plane","company_name":"Tailscale","first_published":"2026-07-29T14:52:14-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Provide guidance, mentorship, and career development for a team of software engineers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods.\u0026lt;br\u0026gt;Pods work across the codebase to implement features, address shortcomings, and answer customer requests.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help your team to improve their performance, the quality of their work; make major design decisions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background building and operating production services with high availability and performance targets.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Expertise managing on call rotations and incident response\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A highly technical manager, able to independently evaluate complex technical tradeoffs in design conversations while leaning on experts in the team for design and implementation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing in Go, used for much of the system\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$206,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$257,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4719580005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4447228005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4719580005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"371","title":"Engineering Manager, Control Plane","company_name":"Tailscale","first_published":"2026-07-29T14:52:12-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Provide guidance, mentorship, and career development for a team of software engineers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods.\u0026lt;br\u0026gt;Pods work across the codebase to implement features, address shortcomings, and answer customer requests.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help your team to improve their performance, the quality of their work; make major design decisions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background building and operating production services with high availability and performance targets.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Expertise managing on call rotations and incident response\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A highly technical manager, able to independently evaluate complex technical tradeoffs in design conversations while leaning on experts in the team for design and implementation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing in Go, used for much of the system\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$276,040\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$344,380 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4738200005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4456585005,"location":{"name":"Remote (New York, New York, United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4738200005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-EAE","title":"Enterprise Account Executive","company_name":"Tailscale","first_published":"2026-09-28T13:44:43-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs. We are one of the fastest-growing VC-backed Dev Tool companies and are looking for folks to help us get to our next stage of growth. You will join a team helping define the future of secure connectivity and modern networking. Tailscale\u0026#39;s product-led growth has created significant enterprise demand from organizations looking to simplify network access, strengthen security, and accelerate developer productivity. As an Enterprise Account Executive, you will work with some of the world\u0026#39;s most sophisticated technology organizations to help them modernize legacy networking and security infrastructure.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are looking for enterprise sellers who know how to create opportunities, not just manage them. You are comfortable building executive relationships, navigating complex organizations, and earning credibility with both technical and business stakeholders. You understand how to translate technical capabilities into measurable business outcomes and can lead customers through transformational technology decisions.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting and networking.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take ownership of the full sales cycle from lead to close\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Position Tailscale as a strategic platform for secure connectivity and modern network access by helping customers understand both the technical and business value of the solution\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of closing experience in a sales role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven track record of consistently meeting or exceeding quota in an enterprise sales environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to engage credibly with both technical practitioners and senior business leaders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating and working with a Sales Engineer on sales cycles\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong account planning, discovery, and business case development skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience closing six-figure enterprise opportunities is strongly preferred\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Location: Remote, but based in or near New York City as it supports customers and requires occasional travel/commute within the assigned region.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What Success Looks Like\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Consistently exceed quota through a combination of self-generated pipeline, new customer acquisition, and account expansion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Establish trusted advisor relationships with Security, Infrastructure, and Engineering leaders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Successfully drive adoption from initial deployment to broader organizational standardization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a predictable pipeline through disciplined prospecting and strategic account development\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$250,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$300,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4738677005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4456585005,"location":{"name":"Remote (San Francisco, California, United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4738677005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-EAE","title":"Enterprise Account Executive","company_name":"Tailscale","first_published":"2026-09-28T16:21:31-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs. We are one of the fastest-growing VC-backed Dev Tool companies and are looking for folks to help us get to our next stage of growth. You will join a team helping define the future of secure connectivity and modern networking. Tailscale\u0026#39;s product-led growth has created significant enterprise demand from organizations looking to simplify network access, strengthen security, and accelerate developer productivity. As an Enterprise Account Executive, you will work with some of the world\u0026#39;s most sophisticated technology organizations to help them modernize legacy networking and security infrastructure.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are looking for enterprise sellers who know how to create opportunities, not just manage them. You are comfortable building executive relationships, navigating complex organizations, and earning credibility with both technical and business stakeholders. You understand how to translate technical capabilities into measurable business outcomes and can lead customers through transformational technology decisions.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting and networking.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take ownership of the full sales cycle from lead to close\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Position Tailscale as a strategic platform for secure connectivity and modern network access by helping customers understand both the technical and business value of the solution\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of closing experience in a sales role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven track record of consistently meeting or exceeding quota in an enterprise sales environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to engage credibly with both technical practitioners and senior business leaders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating and working with a Sales Engineer on sales cycles\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong account planning, discovery, and business case development skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience closing six-figure enterprise opportunities is strongly preferred\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Location: Remote, but based in or near San Francisco as it supports customers and requires occasional travel/commute within the assigned region.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What Success Looks Like\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Consistently exceed quota through a combination of self-generated pipeline, new customer acquisition, and account expansion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Establish trusted advisor relationships with Security, Infrastructure, and Engineering leaders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Successfully drive adoption from initial deployment to broader organizational standardization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a predictable pipeline through disciplined prospecting and strategic account development\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$250,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$300,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724897005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449873005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724897005,"updated_at":"2026-10-16T17:18:44-04:00","requisition_id":"EVG-CSP-FDE","title":"Forward Deployed Engineer","company_name":"Tailscale","first_published":"2026-08-17T14:13:02-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;As a Forward Deployed Engineer at Tailscale, you’ll be the bridge between our technical capabilities and the needs of our most strategic customers. You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey. This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach to ensure customers are fully empowered to leverage the power of Tailscale. The role will report directly to the Team Lead, Customer Success Engineers.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design and build novel solutions to complex customer challenges that fall outside Tailscale’s standard deployment patterns (e.g., prototyping custom integrations, tooling, and network architecture; using structured experimentation and testing to validate solutions for bespoke client uses)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Turn one-off customer solutions into repeatable, reusable assets such as reference architectures, deployment frameworks, and tooling, that can be applied across the broader customer base.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale. Provide training and resources that set customers up for long-term success.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Offer technical support for customers, diagnosing and resolving issues across Tailscale\u0026#39;s platform. Assist with configuration, integration, and troubleshooting to ensure smooth implementation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct QBRs with customers to review usage, success metrics, and future goals. Use these touchpoints to identify opportunities for deeper engagement and horizontal expansion.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build strong relationships with customers, acting as a trusted advisor. Help customers optimize their use of Tailscale by identifying best practices, and by providing recommendations based on their specific use cases and desired business outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as the voice of the customer internally, relaying feedback and insights to the product and engineering teams to help improve the product and the customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work closely with sales, product, engineering, and support teams to ensure smooth handoffs, escalate critical issues, and drive customer success across the organization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve. Share insights and best practices with both the customer and internal teams.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ Years in a technical role with minimum 2 years of customer-facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with enterprise customers in a consultative capacity\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to clearly explain complex technical concepts to a diverse audience, from non-technical stakeholders to engineers. Strong written and verbal communication skills are a must\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analytical mindset and troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A passion for delivering excellent customer service and a strong focus on building long-term customer relationships\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track. Strong time management and organizational skills are key\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams to deliver customer success\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$150,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$250,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4134423005,"name":"Customer Success","child_ids":[],"parent_id":4039044005}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724854005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449873005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724854005,"updated_at":"2026-10-16T17:18:28-04:00","requisition_id":"EVG-CSP-FDE","title":"Forward Deployed Engineer","company_name":"Tailscale","first_published":"2026-08-17T14:13:02-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;As a Forward Deployed Engineer at Tailscale, you’ll be the bridge between our technical capabilities and the needs of our most strategic customers. You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey. This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach to ensure customers are fully empowered to leverage the power of Tailscale. The role will report directly to the Team Lead, Customer Success Engineers.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design and build novel solutions to complex customer challenges that fall outside Tailscale’s standard deployment patterns (e.g., prototyping custom integrations, tooling, and network architecture; using structured experimentation and testing to validate solutions for bespoke client uses)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Turn one-off customer solutions into repeatable, reusable assets such as reference architectures, deployment frameworks, and tooling, that can be applied across the broader customer base.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale. Provide training and resources that set customers up for long-term success.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Offer technical support for customers, diagnosing and resolving issues across Tailscale\u0026#39;s platform. Assist with configuration, integration, and troubleshooting to ensure smooth implementation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct QBRs with customers to review usage, success metrics, and future goals. Use these touchpoints to identify opportunities for deeper engagement and horizontal expansion.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build strong relationships with customers, acting as a trusted advisor. Help customers optimize their use of Tailscale by identifying best practices, and by providing recommendations based on their specific use cases and desired business outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as the voice of the customer internally, relaying feedback and insights to the product and engineering teams to help improve the product and the customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work closely with sales, product, engineering, and support teams to ensure smooth handoffs, escalate critical issues, and drive customer success across the organization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve. Share insights and best practices with both the customer and internal teams.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ Years in a technical role with minimum 2 years of customer-facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with enterprise customers in a consultative capacity\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to clearly explain complex technical concepts to a diverse audience, from non-technical stakeholders to engineers. Strong written and verbal communication skills are a must\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analytical mindset and troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A passion for delivering excellent customer service and a strong focus on building long-term customer relationships\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track. Strong time management and organizational skills are key\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams to deliver customer success\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$335,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4134423005,"name":"Customer Success","child_ids":[],"parent_id":4039044005}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4735072005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454802005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4735072005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"425","title":"Head of Legal","company_name":"Tailscale","first_published":"2026-09-18T09:40:46-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for a pragmatic, business-minded Head of Legal to build and lead our legal function through our next stage of growth.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As Tailscale’s senior legal leader, you’ll partner with executives and teams across the company to navigate complex legal and business considerations, manage risk, and build the capabilities needed to support a growing, globally distributed technology company.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is an opportunity to shape how Legal operates at Tailscale. You’ll establish priorities, advise on important company and product decisions, and determine the right combination of internal talent, outside counsel, processes, and systems to support the business. An early priority will be strengthening our commercial legal capabilities, including hiring a dedicated leader to own contracts and help scale our approach to commercial transactions.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You may already lead a broad legal organization, or you may be an experienced legal leader who has taken on progressively greater responsibility and is ready to step into the top legal role for the first time.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as a trusted advisor to executives and cross-functional leaders, translating legal complexity into clear, practical business guidance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help leaders identify material risks, evaluate tradeoffs, and move forward with appropriate safeguards.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams on company priorities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advise across a range of matters that may include corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable legal processes, policies, systems, and decision-making frameworks without creating unnecessary complexity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Determine which legal capabilities should be developed internally, delegated to future team members, or supported by outside counsel.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hire and empower legal team members, including building a dedicated commercial legal capability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Select and manage outside counsel across the countries where Tailscale operates, balancing expertise, responsiveness, cost, and business impact.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Coordinate guidance across jurisdictions and translate local requirements into practical, consistent company practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support strategic partnerships, corporate initiatives, and other business-critical matters as Tailscale continues to grow.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Anticipate emerging legal and regulatory developments and help the company prepare for what comes next.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Significant legal experience, including meaningful in-house experience within a technology company and a track record of helping legal functions scale in startup or high-growth environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Progressive growth in the scope, complexity, ownership, and influence of your work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Broad business judgment and the ability to navigate legal issues beyond a single area of specialization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience advising executives and senior leaders on complex or consequential decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to understand business goals, identify material risks, and recommend practical paths forward.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering effectively with technical, operational, and commercial teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with the legal considerations facing a growing software or technology company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with outside counsel and turning specialized advice into clear recommendations for the business.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of building or improving legal capabilities, teams, programs, processes, or areas of practice.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong communication skills and the ability to make complex issues understandable to different audiences.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Sound judgment, curiosity, and the confidence to challenge constructively when needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in ambiguity and moving between strategic leadership and hands-on execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Admission and good standing with at least one applicable state, provincial, or other recognized bar association.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We do not expect candidates to bring experience in every area below. Relevant experience may include:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Developer tools, infrastructure, cloud, networking, cybersecurity, data, or another technically complex software environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Open-source software, licensing, developer ecosystems, APIs, integrations, marketplaces, or technology partnerships.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Product counseling, privacy, data governance, cybersecurity, intellectual property, or emerging technology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;AI-enabled products or the use of AI within company operations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Cloud, on-premises, self-hosted, or hybrid software offerings.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Data residency, sovereignty, localization, or cross-border data considerations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Supporting employees or business operations across multiple countries.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Corporate governance, financing, strategic transactions, or board-related matters.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Building or scaling a legal function within a growth-stage company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hiring, developing, or leading in-house legal professionals.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;How You’ll Work\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;At Tailscale, Legal is a thoughtful and pragmatic partner. You’ll seek to understand the goals behind the work, help teams evaluate tradeoffs, and build frameworks that enable people to make sound decisions with increasing independence.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll thrive in this role if you enjoy building, are curious about technical products, and want to shape a legal function as the company grows. You know when to engage directly, when to bring in specialized expertise, and when to empower others to lead.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$223,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$319,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044818005,"name":"Office of the CEO","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4734399005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454802005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4734399005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"425","title":"Head of Legal","company_name":"Tailscale","first_published":"2026-09-18T09:40:45-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for a pragmatic, business-minded Head of Legal to build and lead our legal function through our next stage of growth.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As Tailscale’s senior legal leader, you’ll partner with executives and teams across the company to navigate complex legal and business considerations, manage risk, and build the capabilities needed to support a growing, globally distributed technology company.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is an opportunity to shape how Legal operates at Tailscale. You’ll establish priorities, advise on important company and product decisions, and determine the right combination of internal talent, outside counsel, processes, and systems to support the business. An early priority will be strengthening our commercial legal capabilities, including hiring a dedicated leader to own contracts and help scale our approach to commercial transactions.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You may already lead a broad legal organization, or you may be an experienced legal leader who has taken on progressively greater responsibility and is ready to step into the top legal role for the first time.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as a trusted advisor to executives and cross-functional leaders, translating legal complexity into clear, practical business guidance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help leaders identify material risks, evaluate tradeoffs, and move forward with appropriate safeguards.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams on company priorities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advise across a range of matters that may include corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable legal processes, policies, systems, and decision-making frameworks without creating unnecessary complexity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Determine which legal capabilities should be developed internally, delegated to future team members, or supported by outside counsel.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hire and empower legal team members, including building a dedicated commercial legal capability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Select and manage outside counsel across the countries where Tailscale operates, balancing expertise, responsiveness, cost, and business impact.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Coordinate guidance across jurisdictions and translate local requirements into practical, consistent company practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support strategic partnerships, corporate initiatives, and other business-critical matters as Tailscale continues to grow.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Anticipate emerging legal and regulatory developments and help the company prepare for what comes next.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Significant legal experience, including meaningful in-house experience within a technology company and a track record of helping legal functions scale in startup or high-growth environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Progressive growth in the scope, complexity, ownership, and influence of your work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Broad business judgment and the ability to navigate legal issues beyond a single area of specialization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience advising executives and senior leaders on complex or consequential decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to understand business goals, identify material risks, and recommend practical paths forward.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering effectively with technical, operational, and commercial teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with the legal considerations facing a growing software or technology company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with outside counsel and turning specialized advice into clear recommendations for the business.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of building or improving legal capabilities, teams, programs, processes, or areas of practice.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong communication skills and the ability to make complex issues understandable to different audiences.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Sound judgment, curiosity, and the confidence to challenge constructively when needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in ambiguity and moving between strategic leadership and hands-on execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Admission and good standing with at least one applicable state, provincial, or other recognized bar association.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We do not expect candidates to bring experience in every area below. Relevant experience may include:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Developer tools, infrastructure, cloud, networking, cybersecurity, data, or another technically complex software environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Open-source software, licensing, developer ecosystems, APIs, integrations, marketplaces, or technology partnerships.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Product counseling, privacy, data governance, cybersecurity, intellectual property, or emerging technology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;AI-enabled products or the use of AI within company operations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Cloud, on-premises, self-hosted, or hybrid software offerings.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Data residency, sovereignty, localization, or cross-border data considerations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Supporting employees or business operations across multiple countries.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Corporate governance, financing, strategic transactions, or board-related matters.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Building or scaling a legal function within a growth-stage company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hiring, developing, or leading in-house legal professionals.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;How You’ll Work\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;At Tailscale, Legal is a thoughtful and pragmatic partner. You’ll seek to understand the goals behind the work, help teams evaluate tradeoffs, and build frameworks that enable people to make sound decisions with increasing independence.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll thrive in this role if you enjoy building, are curious about technical products, and want to shape a legal function as the company grows. You know when to engage directly, when to bring in specialized expertise, and when to empower others to lead.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$298,820\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$427,460 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044818005,"name":"Office of the CEO","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4733404005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454334005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4733404005,"updated_at":"2026-10-10T11:36:31-04:00","requisition_id":"424","title":"Infrastructure Engineer","company_name":"Tailscale","first_published":"2026-10-10T11:36:31-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Support and enable internal business units through shared engineering services and functionalities, building the tools and processes for those teams to succeed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build relationships with multiple stakeholders across the organization to understand and meet their needs with projects you\u0026#39;ll own end to end.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work directly with internal customer facing teams to empower their mission and take pride in making their day-to-day lives easier. Work with product engineering to extract the data needed to drive business decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Example deliverables in this role might include:\u0026lt;/li\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Improve observability through metrics, alerting, logging and telemetry integration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and build improvements for Continuous Deployment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Utilize infrastructure as code to make changes in a cloud environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with other engineering teams to build cross functional infrastructure improvements\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Automate upgrades for managed services and VMs.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully-remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfortably work asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work as part of a team of engineers to design, build, test, and document core software components.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analyze and improve efficiency, scalability, and stability of various system resources.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience with CI/CD, secrets management, infrastructure as code, and observability\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with distributed systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with operating managed services in a cloud environment (preferably AWS)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with operating Kubernetes in production is a strong plus\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with networks (IP addressing, routing, etc.)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Most of the non-front-end portions of the system are developed in the Go programming language. Experience with Go is a plus.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$181,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$226,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4015351005,"name":"Remote (United Kingdom)","location":"United Kingdom","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4733403005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454334005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4733403005,"updated_at":"2026-10-10T11:36:28-04:00","requisition_id":"424","title":"Infrastructure Engineer","company_name":"Tailscale","first_published":"2026-10-10T11:36:28-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Support and enable internal business units through shared engineering services and functionalities, building the tools and processes for those teams to succeed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build relationships with multiple stakeholders across the organization to understand and meet their needs with projects you\u0026#39;ll own end to end.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work directly with internal customer facing teams to empower their mission and take pride in making their day-to-day lives easier. Work with product engineering to extract the data needed to drive business decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Example deliverables in this role might include:\u0026lt;/li\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Improve observability through metrics, alerting, logging and telemetry integration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and build improvements for Continuous Deployment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Utilize infrastructure as code to make changes in a cloud environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with other engineering teams to build cross functional infrastructure improvements\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Automate upgrades for managed services and VMs.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully-remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfortably work asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work as part of a team of engineers to design, build, test, and document core software components.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analyze and improve efficiency, scalability, and stability of various system resources.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience with CI/CD, secrets management, infrastructure as code, and observability\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with distributed systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with operating managed services in a cloud environment (preferably AWS)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with operating Kubernetes in production is a strong plus\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with networks (IP addressing, routing, etc.)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Most of the non-front-end portions of the system are developed in the Go programming language. Experience with Go is a plus.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$218,420\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$273,360 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4015351005,"name":"Remote (United Kingdom)","location":"United Kingdom","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4733571005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454225005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4733571005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"423","title":"Manager, Developer Relations Engineering","company_name":"Tailscale","first_published":"2026-09-14T09:26:47-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong program management skills, including planning, prioritization, delegation, and proactive risk communication\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to balance hands-on execution with team leadership and long-term program development\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Low ego, high horsepower with a “yes, and” mindset to collaboration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have tried and used Tailscale\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting product-led growth or self-serve adoption\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building technical integrations, example applications, community tools, or open-source projects\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing new public-facing technical voices within a team or company\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing agency partners, contractors, program budgets, or external contributors\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in a fast-paced startup or scale-up environment\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$161,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4733161005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454225005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4733161005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"423","title":"Manager, Developer Relations Engineering","company_name":"Tailscale","first_published":"2026-09-14T09:26:45-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong program management skills, including planning, prioritization, delegation, and proactive risk communication\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to balance hands-on execution with team leadership and long-term program development\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Low ego, high horsepower with a “yes, and” mindset to collaboration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have tried and used Tailscale\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting product-led growth or self-serve adoption\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building technical integrations, example applications, community tools, or open-source projects\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing new public-facing technical voices within a team or company\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing agency partners, contractors, program budgets, or external contributors\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in a fast-paced startup or scale-up environment\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$215,740\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$269,340 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4713959005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4444428005,"location":{"name":"Hybrid (Vancouver, British Columbia)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4713959005,"updated_at":"2026-10-07T16:03:14-04:00","requisition_id":"EVG-NBAE","title":"New Business Account Executive","company_name":"Tailscale","first_published":"2026-07-14T15:11:48-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role. You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline. You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale has a vibrant community across Hacker News, X, and Reddit. We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world. This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support customers across all time zones\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage and organize your activities, pipeline, and forecast in Gong and Salesforce\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;1+ years of prospecting or closing experience in a door-to-door or in-person sales role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ambition to build (and not just follow) a sales playbook\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A technical background or curiosity in technology\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and presentation skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience self sourcing opportunities and guiding a customer from discovery all the way through closed won deals\u0026lt;/li\u0026gt;\n\u0026lt;li style=\u0026quot;font-weight: bold;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;This role is based in Vancouver and hybrid required (3 days/week in-office)\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$167,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053186005,"name":"Hybrid (Vancouver)","location":"Vancouver, British Columbia, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4718667005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4446752005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4718667005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"369","title":"Product Marketing Manager","company_name":"Tailscale","first_published":"2026-07-27T09:41:03-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for a collaborative and analytical Product Marketing Manager to join the marketing team at Tailscale. You will work closely with product, marketing, and revenue teams to identify customer needs, pain points, and articulate “Why Tailscale?” and then turn these insights into actionable assets for us to go-to-market with. This role might be perfect for you if you are familiar with PAM, networking infrastructure, or enterprise security needs, and can communicate technical features as easy-to-digest benefits. If you love highly cross-functional work and want to help a rapidly growing sales and revenue team succeed, read on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who is comfortable working asynchronously, thrives in ambiguity and has a focus on getting it right, not being right.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Becoming the expert on our users and customers — who they are, what their pain points are, and what drives them to seek out solutions\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborating with sales, product and marketing teams to develop and refine product positioning, messaging, and effective content\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Launching new products or features, managing cross-functional projects associated with that launch, and measuring revenue and pipeline generated\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Creating sales collateral and enablement materials— slide decks, one-pagers, training sessions, customer case studies, webinars, etc.. This includes delegating and working with designers/web developers/content marketers as needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Performing competitive and market analysis to inform messaging and campaigns, and influence product strategy\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Represent PMM at industry events by delivering demos and gathering firsthand customer and prospect insights to shape messaging and campaign strategy\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Helping drive meaningful sales pipeline\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;At least 5+ years of experience in product marketing, working with sales teams, and sales enablement\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A proven track record in marketing, product marketing, sales enablement, product management, or a related field with a minimum of 5+ years of direct experience\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;An affinity for complex, highly technical subjects\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing interdependent, complex projects and keeping multiple work streams on track\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;An analytical and data-driven mindset with an enthusiasm for problem-solving and measuring the effectiveness of your work\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to quickly adapt and react to changing plans and ambiguity.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent people skills - this role will interact with many cross-functional teams and the ability to communicate and negotiate effectively will be critical to the success of this role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A bias toward action, execution, and iteration\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Start up experience\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with networking or security products used in SaaS or cloud environments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$190,280\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$237,180 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4718672005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4446752005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4718672005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"369","title":"Product Marketing Manager","company_name":"Tailscale","first_published":"2026-07-27T09:41:04-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for a collaborative and analytical Product Marketing Manager to join the marketing team at Tailscale. You will work closely with product, marketing, and revenue teams to identify customer needs, pain points, and articulate “Why Tailscale?” and then turn these insights into actionable assets for us to go-to-market with. This role might be perfect for you if you are familiar with PAM, networking infrastructure, or enterprise security needs, and can communicate technical features as easy-to-digest benefits. If you love highly cross-functional work and want to help a rapidly growing sales and revenue team succeed, read on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who is comfortable working asynchronously, thrives in ambiguity and has a focus on getting it right, not being right.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Becoming the expert on our users and customers — who they are, what their pain points are, and what drives them to seek out solutions\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborating with sales, product and marketing teams to develop and refine product positioning, messaging, and effective content\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Launching new products or features, managing cross-functional projects associated with that launch, and measuring revenue and pipeline generated\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Creating sales collateral and enablement materials— slide decks, one-pagers, training sessions, customer case studies, webinars, etc.. This includes delegating and working with designers/web developers/content marketers as needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Performing competitive and market analysis to inform messaging and campaigns, and influence product strategy\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Represent PMM at industry events by delivering demos and gathering firsthand customer and prospect insights to shape messaging and campaign strategy\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Helping drive meaningful sales pipeline\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;At least 5+ years of experience in product marketing, working with sales teams, and sales enablement\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A proven track record in marketing, product marketing, sales enablement, product management, or a related field with a minimum of 5+ years of direct experience\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;An affinity for complex, highly technical subjects\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing interdependent, complex projects and keeping multiple work streams on track\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;An analytical and data-driven mindset with an enthusiasm for problem-solving and measuring the effectiveness of your work\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to quickly adapt and react to changing plans and ambiguity.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent people skills - this role will interact with many cross-functional teams and the ability to communicate and negotiate effectively will be critical to the success of this role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A bias toward action, execution, and iteration\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Start up experience\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with networking or security products used in SaaS or cloud environments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$144,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$177,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4744878005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4459690005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4744878005,"updated_at":"2026-10-16T22:12:47-04:00","requisition_id":"478","title":"Program Manager, EPD Operations","company_name":"Tailscale","first_published":"2026-10-16T22:12:47-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re seeking a talented and motivated full-time Program Manager to join our team. This is a \u0026lt;strong\u0026gt;tactical, implementation-focused role\u0026lt;/strong\u0026gt;, hands-on in shaping how EPD (Engineering, Product \u0026amp;amp; Design) operates, works together, and stays productive: building and refining the processes and rhythms that keep the org running, driving improvement initiatives over time, and owning the processes behind EPD\u0026#39;s operational health. You\u0026#39;ll help the team understand trends and spot where improvements are needed.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Because we\u0026#39;re an early-stage and fully remote company, we\u0026#39;re looking for an individual who can work independently to align the teams involved in building the product. A deep understanding of the technical engineering space (how engineering teams operate, where the friction points typically live, and what good looks like) is essential to being effective and credible in this role. Ability to think on one\u0026#39;s feet, enjoy collaborating with highly technical teams, operate comfortably in ambiguity without a clearly defined deliverable, and be comfortable working asynchronously is essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;You will work as part of the TPM team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own the processes for bug tracking, incidents, reliability, and escalations, and continuously improve them to drive efficiency and progress toward EPD\u0026#39;s operational health goals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Spot trends across operational health data and translate them into clear insights on how EPD is doing and where improvement is needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build dashboards and reports in tools like Jira and Snowflake that give EPD and the broader company visibility into operational health and progress.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Turn data into a clear story: what it\u0026#39;s telling us, why it matters, and what needs to change, then design and implement the process changes to act on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify process gaps with EPD and proactively develop just the right amount of process to fill the gap: not too much, not too little.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support planning activities and project tracking processes, helping keep them running smoothly and consistently across EPD.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help run project status reviews, leadership roadmap reviews, and priority reviews, making sure the right information is ready and the right people are in the room.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Connect the dots across systems, processes, and teams, spotting where disconnected efforts overlap, conflict, or could be simplified, and acting on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Jump in on whatever initiative pops up in EPD that needs support, structure, or someone to help carry it forward, whether or not it fits inside a defined program.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Handle project retrospectives involving participants and stakeholders to understand what went well and what should be adjusted in future project work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Seek opportunities to bring about ongoing improvement and simplification in business operating procedures and practices, leading to improved efficiency and effectiveness.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience as a Program Manager or Technical Program Manager (TPM), coordinating with stakeholders and cross-functional teams, particularly experience working closely within Engineering and with Product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience as a Program/Technical Program Manager in a remote startup environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A deep, working understanding of the technical engineering space, including how engineering teams operate day to day, common workflows and tooling, and where technical and process friction tend to show up.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience owning operational health processes, such as bug tracking, incidents, reliability, or escalations, and using them to drive measurable efficiency gains.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong data skills, including building dashboards and reports in tools like Jira and Snowflake, and a solid understanding of how to read and interpret data.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to spot trends in data and translate them into a clear story: what\u0026#39;s happening, why it matters, and what should change, paired with the ability to design and implement the process changes needed to act on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting planning cycles, project tracking, and recurring reviews, such as project status reviews or leadership roadmap and priority reviews.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A comfort level with ambiguity and undefined deliverables. You\u0026#39;re motivated by taming chaos and improving how things run, not just shipping a fixed checklist.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A tactical, execution-first orientation: you\u0026#39;re energized by hands-on implementation and getting things done, more than by high-level strategy or planning alone.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with Engineering, Product, and Design leadership, understanding their motivations and priorities, and using that to help move initiatives forward and communicate goals across the company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to communicate openly, supporting and championing innovation and inclusivity, in both written and verbal communication.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Agile methodologies and project management tools, such as Jira, Notion and GitHub.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with technical solutions, engineering practices, and the security and engineering lifecycle.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$114,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$143,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044817005,"name":"Operations","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4744876005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4459690005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4744876005,"updated_at":"2026-10-16T22:12:45-04:00","requisition_id":"478","title":"Program Manager, EPD Operations","company_name":"Tailscale","first_published":"2026-10-16T22:12:45-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re seeking a talented and motivated full-time Program Manager to join our team. This is a \u0026lt;strong\u0026gt;tactical, implementation-focused role\u0026lt;/strong\u0026gt;, hands-on in shaping how EPD (Engineering, Product \u0026amp;amp; Design) operates, works together, and stays productive: building and refining the processes and rhythms that keep the org running, driving improvement initiatives over time, and owning the processes behind EPD\u0026#39;s operational health. You\u0026#39;ll help the team understand trends and spot where improvements are needed.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Because we\u0026#39;re an early-stage and fully remote company, we\u0026#39;re looking for an individual who can work independently to align the teams involved in building the product. A deep understanding of the technical engineering space (how engineering teams operate, where the friction points typically live, and what good looks like) is essential to being effective and credible in this role. Ability to think on one\u0026#39;s feet, enjoy collaborating with highly technical teams, operate comfortably in ambiguity without a clearly defined deliverable, and be comfortable working asynchronously is essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;You will work as part of the TPM team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own the processes for bug tracking, incidents, reliability, and escalations, and continuously improve them to drive efficiency and progress toward EPD\u0026#39;s operational health goals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Spot trends across operational health data and translate them into clear insights on how EPD is doing and where improvement is needed.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build dashboards and reports in tools like Jira and Snowflake that give EPD and the broader company visibility into operational health and progress.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Turn data into a clear story: what it\u0026#39;s telling us, why it matters, and what needs to change, then design and implement the process changes to act on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify process gaps with EPD and proactively develop just the right amount of process to fill the gap: not too much, not too little.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support planning activities and project tracking processes, helping keep them running smoothly and consistently across EPD.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help run project status reviews, leadership roadmap reviews, and priority reviews, making sure the right information is ready and the right people are in the room.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Connect the dots across systems, processes, and teams, spotting where disconnected efforts overlap, conflict, or could be simplified, and acting on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Jump in on whatever initiative pops up in EPD that needs support, structure, or someone to help carry it forward, whether or not it fits inside a defined program.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Handle project retrospectives involving participants and stakeholders to understand what went well and what should be adjusted in future project work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Seek opportunities to bring about ongoing improvement and simplification in business operating procedures and practices, leading to improved efficiency and effectiveness.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience as a Program Manager or Technical Program Manager (TPM), coordinating with stakeholders and cross-functional teams, particularly experience working closely within Engineering and with Product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience as a Program/Technical Program Manager in a remote startup environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A deep, working understanding of the technical engineering space, including how engineering teams operate day to day, common workflows and tooling, and where technical and process friction tend to show up.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience owning operational health processes, such as bug tracking, incidents, reliability, or escalations, and using them to drive measurable efficiency gains.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong data skills, including building dashboards and reports in tools like Jira and Snowflake, and a solid understanding of how to read and interpret data.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to spot trends in data and translate them into a clear story: what\u0026#39;s happening, why it matters, and what should change, paired with the ability to design and implement the process changes needed to act on it.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting planning cycles, project tracking, and recurring reviews, such as project status reviews or leadership roadmap and priority reviews.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A comfort level with ambiguity and undefined deliverables. You\u0026#39;re motivated by taming chaos and improving how things run, not just shipping a fixed checklist.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A tactical, execution-first orientation: you\u0026#39;re energized by hands-on implementation and getting things done, more than by high-level strategy or planning alone.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working with Engineering, Product, and Design leadership, understanding their motivations and priorities, and using that to help move initiatives forward and communicate goals across the company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to communicate openly, supporting and championing innovation and inclusivity, in both written and verbal communication.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Agile methodologies and project management tools, such as Jira, Notion and GitHub.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with technical solutions, engineering practices, and the security and engineering lifecycle.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$152,760\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$191,620 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4044817005,"name":"Operations","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4723401005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449161005,"location":{"name":"Hybrid (London, England, United Kingdom)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4723401005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"384","title":"Sales Director, EMEA","company_name":"Tailscale","first_published":"2026-08-11T19:07:49-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;Tailscale is redefining secure networking by making it simple for organizations to securely connect people, devices, and workloads anywhere in the world.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;At Tailscale, we\u0026#39;re solving one of the most fundamental challenges in modern infrastructure: secure connectivity. Our product is loved by developers, trusted by IT and security teams, and rapidly expanding within organizations of every size. As adoption accelerates, we are investing in a regional sales motion that matches the scale of our ambition across EMEA.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are looking for a founding Sales Director, EMEA to build and lead one of Tailscale\u0026#39;s most important growth initiatives. This is a rare opportunity to shape how a category-leading company enters and scales a major region, develops strategic customer and partner relationships, recruits an exceptional team, and creates the operating model for long-term growth.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;You will be a regional leader, seller, coach, and builder. You will own the EMEA sales strategy and lead teams across multiple customer segments, while personally helping advance the region\u0026#39;s most important opportunities and executive relationships.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You will define regional priorities, territory and segment strategy, hiring plans, outbound and expansion motions, and the operating cadence for the business. You will also help spearhead partnerships across the region, including channel, cloud, technology, and strategic alliance relationships that can accelerate customer acquisition and expansion.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Initially, you will lead a focused team of Account Executives across multiple segments and work closely with Customer Engineering, RevOps, Marketing, GTM Engineering, and Executive Leadership. As the business grows, you will play a central role in scaling the team, developing frontline leaders, and building the regional organization.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This UK-based role reports directly to the President and offers the opportunity to build Tailscale’s EMEA sales organization from the ground up.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Build the EMEA Business\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Lead\u0026amp;nbsp; the current team and build the EMEA sales organization and go-to-market motion.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Develop the regional strategy, operating model, territory design, account segmentation, and coverage plan across multiple sales segments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Set clear regional priorities and translate company goals into executable plans for new business, expansion, and partnerships.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Establish repeatable playbooks that reflect the needs of customers and markets across the UK and broader EMEA region.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Provide regional market insight that helps shape company strategy, product priorities, and investment decisions.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Lead From the Front\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Personally support and, when appropriate, lead Tailscale\u0026#39;s highest-value and most strategic EMEA opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Develop trusted executive relationships with CIOs, CISOs, CTOs, infrastructure leaders, security leaders, and business executives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Serve as the regional executive sponsor and quarterback for complex, multi-stakeholder sales cycles.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Coach teams on discovery, qualification, account strategy, executive engagement, negotiation, and deal execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Navigate technical, commercial, legal, procurement, and executive stakeholders to drive successful customer outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Lead and Scale Multiple Segments\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Lead Account Executives serving multiple customer segments, from commercial and mid-market organizations through enterprise and accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Create differentiated motions, coverage models, and performance expectations appropriate to each segment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Recruit, hire, onboard, and develop exceptional sales talent across the region.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Build a high-performance culture grounded in accountability, collaboration, curiosity, customer value, and continuous learning.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Develop future leaders and create the management structure required as the EMEA organization scales.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Build Regional Partnerships\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Help define and execute the EMEA partnership strategy alongside the Partnerships organization and Executive Leadership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Identify markets and customer segments where partners can accelerate awareness, pipeline creation, implementation, and expansion.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Create clear rules of engagement, joint account plans, and co-selling motions with priority partners.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Represent Tailscale with senior partner executives and at relevant regional customer and industry events.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Create Pipeline and Regional Awareness\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Lead an outbound-first and account-based sales motion across the region.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Personally build executive relationships within high-priority accounts and partner ecosystems.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Partner with SDRs, Marketing, GTM Engineering and Partnerships to create qualified pipeline.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Build scalable account planning, prospecting, event, community, and partner-sourced pipeline programs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Ensure the region develops a balanced pipeline across customer segments, products, countries, and sources.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Drive Operational Excellence\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Own regional forecasting, pipeline health, hiring plans, and performance management.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Establish a rigorous operating cadence across forecast reviews, pipeline creation, deal inspection, account planning, and talent development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Use data to identify trends, improve execution, allocate resources, and communicate regional performance to leadership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Partner closely with Product and Engineering to provide structured customer and market feedback from EMEA.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Build the metrics, processes, and cross-functional relationships required to scale the organization effectively.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;An experienced sales leader who has built or materially scaled a high-growth SaaS business in EMEA.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;A proven leader of teams spanning multiple customer segments, with the judgment to adapt the sales motion by segment and market.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;A builder who is comfortable operating with ambiguity, limited infrastructure, and significant ownership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;A strong seller and coach with a consistent record of winning complex new-business and expansion opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Experienced in recruiting, developing, and retaining high-performing Account Executives and sales leaders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Demonstrated success building outbound pipeline and establishing repeatable regional go-to-market motions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Experienced developing channel, technology, cloud, reseller, or strategic partnership relationships in EMEA.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Executive presence and credibility with CIOs, CISOs, CTOs, and senior business leaders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Strong business acumen and experience navigating complex buying committees, procurement processes, and enterprise sales cycles.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Deep familiarity with the UK and broader EMEA technology market; additional European language skills are valuable but not required.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong data-stringify-type=\u0026quot;bold\u0026quot;\u0026gt;This role is based in London and is hybrid (2-3 days/week in-office) with ability to travel throughout EMEA as needed. \u0026lt;span style=\u0026quot;color: rgb(255, 255, 255);\u0026quot;\u0026gt;#LI-Hybrid\u0026lt;/span\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;You\u0026#39;ll Thrive Here If You...\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Want to build a region rather than inherit a mature organization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Enjoy leading from the front while creating leverage through managers, teams, and partners.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Can balance strategic planning with hands-on customer and deal leadership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Are energized by developing different sales motions for commercial, mid-market, enterprise, and strategic customers.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;See partnerships as a core growth lever rather than a separate or secondary function.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;Want to leave a lasting impact on how a category-leading company expands internationally.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4015351005,"name":"Remote (United Kingdom)","location":"United Kingdom","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4726153005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4450540005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4726153005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"394","title":"Security Infrastructure Engineer","company_name":"Tailscale","first_published":"2026-08-20T16:04:58-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented software engineer, specializing in security and infrastructure, to help grow our product security team. We’re looking for people who can move Tailscale forward while making it safer to use. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design and build security controls across diverse layers (e.g., cloud platforms, OS, Kubernetes, networks, CI/CD) to defend against sophisticated adversaries and insider threats.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, defense-in-depth, and implementing them across our codebase.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Audit Tailscale infrastructure for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support engineering decisions with threat modeling and security analysis and expertise.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will spend 25-50% of your time in this role writing software vs purely operational or governance security responsibilities.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Technical\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Expertise in the security of cloud platforms (e.g., AWS), especially securing multi-cloud networks and infrastructure, and designing cloud agnostic systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with container security, orchestration security, and authentication/authorization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with internet/web security fundamentals: WAF’s, TLS, PKI, DNS security, etc.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency developing in at least one programming language (Tailscale uses Go) and Infrastructure as Code tooling (e.g. Terraform, Ansible)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Prior experience in a safety-related technical role, e.g.:\u0026lt;/li\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;infrastructure security\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;security operations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;threat modeling and prioritization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;digital forensics and incident response\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of operating system internals and security mechanisms\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of common networking protocols\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Act as a Subject Matter Expert during security incidents, focusing on infrastructure-level containment and remediation\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Team Fit\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to work independently and collaboratively\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take a risk-based approach to building security controls, balancing your security expertise and broad technical skillsets with practical, usable solutions\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$163,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$204,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4726152005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4450540005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4726152005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"394","title":"Security Infrastructure Engineer","company_name":"Tailscale","first_published":"2026-08-20T16:04:56-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented software engineer, specializing in security and infrastructure, to help grow our product security team. We’re looking for people who can move Tailscale forward while making it safer to use. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design and build security controls across diverse layers (e.g., cloud platforms, OS, Kubernetes, networks, CI/CD) to defend against sophisticated adversaries and insider threats.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, defense-in-depth, and implementing them across our codebase.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Audit Tailscale infrastructure for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support engineering decisions with threat modeling and security analysis and expertise.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will spend 25-50% of your time in this role writing software vs purely operational or governance security responsibilities.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Technical\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Expertise in the security of cloud platforms (e.g., AWS), especially securing multi-cloud networks and infrastructure, and designing cloud agnostic systems\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with container security, orchestration security, and authentication/authorization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with internet/web security fundamentals: WAF’s, TLS, PKI, DNS security, etc.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency developing in at least one programming language (Tailscale uses Go) and Infrastructure as Code tooling (e.g. Terraform, Ansible)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Prior experience in a safety-related technical role, e.g.:\u0026lt;/li\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;infrastructure security\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;security operations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;threat modeling and prioritization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;digital forensics and incident response\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of operating system internals and security mechanisms\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of common networking protocols\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Act as a Subject Matter Expert during security incidents, focusing on infrastructure-level containment and remediation\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Team Fit\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to work independently and collaboratively\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take a risk-based approach to building security controls, balancing your security expertise and broad technical skillsets with practical, usable solutions\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$218,420\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$273,360 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4724120005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449550005,"location":{"name":"Hybrid (Toronto, Ontario)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4724120005,"updated_at":"2026-10-15T11:53:12-04:00","requisition_id":"EVG-SrCAE-TOR/VAN","title":"Senior Customer Account Executive","company_name":"Tailscale","first_published":"2026-10-15T11:53:12-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years of closing experience in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Toronto and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053580005,"name":"Hybrid (Toronto)","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null},{"id":4053186005,"name":"Hybrid (Vancouver)","location":"Vancouver, British Columbia, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4739774005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457384005,"location":{"name":"Hybrid (San Francisco, California, United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4739774005,"updated_at":"2026-10-01T14:42:34-04:00","requisition_id":"EVG-SrCAE-SF","title":"Senior Customer Account Executive","company_name":"Tailscale","first_published":"2026-10-01T14:42:34-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Sr. Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years of closing experience in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in San Francisco and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$150,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$190,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4065773005,"name":"Hybrid (San Francisco)","location":"San Francisco, California, United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4744215005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4449550005,"location":{"name":"Hybrid (Vancouver, British Columbia)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4744215005,"updated_at":"2026-10-15T11:53:14-04:00","requisition_id":"EVG-SrCAE-TOR/VAN","title":"Senior Customer Account Executive","company_name":"Tailscale","first_published":"2026-10-15T11:53:14-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers\u0026#39; needs.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Become an expert in how Tailscale helps our customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build a credible pipeline every quarter by engaging with clients on upsells and renewals\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own an upsell and renewal number across your accounts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Help educate customers on the value of Tailscale throughout the evaluation \u0026amp;amp; adoption cycle\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Generate short-term results while maintaining annual pipeline coverage\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide accurate weekly forecasting \u0026amp;amp; revenue delivery\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years of closing experience in an AE or an AM role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A strong desire to join a high-growth software startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Has sold developer and/or technical products, especially in a product-led growth (PLG) motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience presenting to senior managers and executives\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using Gong, or similar, to collaborate internally and manage pipeline\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Vancouver and is hybrid required (3 days/week in-office).\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053580005,"name":"Hybrid (Toronto)","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null},{"id":4053186005,"name":"Hybrid (Vancouver)","location":"Vancouver, British Columbia, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4740660005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457856005,"location":{"name":"Hybrid (Toronto, Ontario)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4740660005,"updated_at":"2026-10-07T15:48:38-04:00","requisition_id":"EVG-SrNBAE-TOR","title":"Senior New Business Account Executive","company_name":"Tailscale","first_published":"2026-10-05T17:45:54-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role. You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline. You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale has a vibrant community across Hacker News, X, and Reddit. We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world. This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support customers across all time zones\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage and organize your activities, pipeline, and forecast in Gong and Salesforce\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years of prospecting or closing experience in a door-to-door or in-person sales role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ambition to build (and not just follow) a sales playbook\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A technical background or curiosity in technology\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and presentation skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience self sourcing opportunities and guiding a customer from discovery all the way through closed won deals, with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Toronto and is hybrid required (3 days/week in-office)\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$201,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053580005,"name":"Hybrid (Toronto)","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4722225005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448564005,"location":{"name":"Hybrid (Denver, Colorado, United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4722225005,"updated_at":"2026-10-05T17:37:30-04:00","requisition_id":"EVG-SrNBAE","title":"Senior New Business Account Executive","company_name":"Tailscale","first_published":"2026-08-07T10:32:34-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role. You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline. You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale has a vibrant community across Hacker News, X, and Reddit. We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world. This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support customers across all time zones\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage and organize your activities, pipeline, and forecast in Gong and Salesforce\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years of prospecting or closing experience in a door-to-door or in-person sales role\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ambition to build (and not just follow) a sales playbook\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A technical background or curiosity in technology\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and presentation skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience self sourcing opportunities and guiding a customer from discovery all the way through closed won deals, with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;This role is based in Denver and is hybrid required (3 days/week in-office)\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$120,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$150,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4053187005,"name":"Hybrid (Denver)","location":"Denver, Colorado, United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4741470005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4458233005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4741470005,"updated_at":"2026-10-07T20:27:51-04:00","requisition_id":"EVG-SrSEEnt","title":"Senior Solutions Engineer, Enterprise","company_name":"Tailscale","first_published":"2026-10-07T12:31:14-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We are hiring a Senior Solutions Engineer to partner with Account Executives on enterprise accounts. You will own the technical side of the sales cycle—qualifying use cases, leading discovery and architecture, running demos and proofs-of-concept, and supporting early adoption and expansion. You will act as a trusted advisor to networking, security, platform, and IT stakeholders.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a senior individual-contributor role that blends deep networking and security expertise with consultative selling. You will co-own pipeline outcomes, help close and expand enterprise deals, and feed real customer requirements back into product and go-to-market.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role is a strong fit for a senior SE who wants to stay close to the technology, work enterprise deals from qualification through early adoption, and help customers replace complicated networking—and privileged/AI access—with something simpler and more secure.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with Account Executives to identify, qualify, and close new enterprise logos and expansion opportunities, confirming technical fit aligned with business goals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead technical discovery, solution architecture, demos, and proofs-of-concept (POCs) that help customers make confident buying decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design Tailscale architectures for hybrid, multi-cloud, and on-premises environments, including identity-based access and secure connectivity patterns.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Align Tailscale PAM for identity-aware access with session recording, and Aperture as an AI gateway for LLM/API access.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate technical capabilities into clear business value, including security outcomes, operational simplicity, and time-to-value.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Serve as a trusted advisor across multi-stakeholder deals, guiding implementation and collaborating with Customer Success to drive best-practice adoption.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support security reviews and common enterprise diligence (architecture reviews, questionnaires, and compliance discussions).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide structured feedback to Product, Engineering, and GTM teams based on enterprise use cases, blockers, and competitive dynamics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Assist in building reusable demo environments, solution blueprints, and enablement assets that raise the quality and consistency of enterprise engagements.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Stay current on zero-trust networking, privileged access, identity integrations, cloud networking, and AI access/governance so you can position the full Tailscale portfolio accurately and competitively.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5–7+ years in a customer-facing Solutions Engineer, Sales Engineer, or Solutions Architect role within networking, security, infrastructure, or related enterprise software.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven experience co-owning pipeline and influencing quota outcomes with Sales on both new business and expansion.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC, SCIM).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong networking fundamentals and troubleshooting skills: TCP/IP, DNS, routing, firewalls, NAT traversal, TLS/HTTPS, and related concepts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on systems administration and troubleshooting across Linux and at least one of macOS or Windows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on architecture experience with AWS, GCP, and/or Azure, including hybrid environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience managing cloud and network infrastructure using Infrastructure as Code (Terraform preferred for policy/ACL; Pulumi, Ansible, or CloudFormation also relevant).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication skills, with the ability to explain complex systems clearly and translate technical features into business value for both practitioners and executives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience running technical evaluations, customized demos, and POCs in enterprise or upper mid-market environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in a high-growth, fully distributed environment with a high degree of ownership and competing priorities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Willingness to travel occasionally (approximately 10–20%) for customer meetings, workshops, and internal collaboration.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Nice to Have\u0026amp;nbsp;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience selling or architecting zero-trust, SASE, ZTNA, VPN, PAM, or secure networking solutions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privileged access patterns: JIT access, session recording, least-privilege to SSH/databases/Kubernetes, and replacing shared credentials.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with AI gateways, LLM access governance, MCP/API proxying, or centralized model/provider key management.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on scripting or automation experience (Python, Bash, Go, or similar) for demos, POCs, or integrations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of the competitive landscape in zero-trust, PAM, and AI access control.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting security reviews, architecture diligence, and compliance discussions (SOC 2, HIPAA, PCI) in a pre-sales context.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Previous exposure to Tailscale, WireGuard, or similar mesh-networking technologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience creating reusable architectures, demo environments, or SE playbooks.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$250,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$300,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4742174005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457511005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4742174005,"updated_at":"2026-10-08T18:28:44-04:00","requisition_id":"454","title":"Senior Web Experimentation Manager","company_name":"Tailscale","first_published":"2026-10-08T18:28:44-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re looking for a Senior Web Experimentation Manager to own the experimentation program across Tailscale\u0026#39;s highest-traffic website pages, including the homepage, pricing, use-case pages, and paid landing pages.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You\u0026#39;ll set the roadmap, the test design standards, and the decision rules every experiment runs on, and you\u0026#39;ll design and ship the highest-stakes tests yourself. You\u0026#39;ll work closely with web strategy, web development, design, product marketing, and analytics partners, and you\u0026#39;ll coach the people running tests alongside you.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role is for someone who has run an experimentation program, and not only experiments. You know when a test is the right tool and when a change is better shipped without one. You can hold a decision rule when a result is inconvenient, and you treat a flat result as information. Success means a program the rest of the company trusts, results that hold up to scrutiny, and learnings that change what we build next.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own the experimentation roadmap, from taking in ideas across the team to prioritizing them against traffic, expected impact, and cost.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Set and maintain the standards every test runs on, including sizing, statistical power, minimum detectable effect, guardrail metrics, and the rules for shipping, iterating, or stopping a test.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Review test designs before launch and results before they\u0026#39;re shared, so every number we report is one we can stand behind.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design, build, and run the most consequential experiments yourself, particularly on pricing and the homepage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own the health of our testing platform and measurement with web development and analytics, so tracking works and results reconcile with our analytics data.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain the experiment record as the source of truth for what our website has learned, and turn accumulated results into recommendations for web strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Report program results to marketing leadership: what we learned, what shipped, and what we\u0026#39;re testing next.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Coach contributors across web, design, and marketing on hypothesis quality, test design, and reading results correctly.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6–9 years of experience in conversion optimization, web experimentation, growth marketing, or a related field, including ownership of an experimentation program across multiple pages or products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep experience with a testing platform such as Optimizely, VWO, or a comparable tool, including program-level setup and governance\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong command of experiment statistics, including power and sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, and the risks of peeking and multiple comparisons\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to evaluate a test\u0026#39;s design and validity, and to explain plainly why a result should or shouldn\u0026#39;t be trusted\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort with HTML, CSS, and JavaScript to build and debug client-side variations yourself\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Working proficiency in SQL and an analytics tool such as GA4, enough to validate results independently of the testing platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Sound judgment about when an experiment is the right tool, and when a change is low-risk and reversible enough to ship without one\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear writing and communication, with the ability to present results and tradeoffs to senior stakeholders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience coaching or mentoring others on experimentation, formally or informally\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort working in a remote-first, async environment\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience experimenting on pricing pages, or on pages that route visitors between self-serve and sales-assisted paths\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with B2B SaaS, developer tools, infrastructure, or cybersecurity products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with server-side or feature-flag testing, or with Bayesian or sequential testing methods\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience moving an experimentation program from one testing platform to another\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with accessibility and web performance considerations in test builds\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building an experiment library that other teams use\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$114,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$145,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4739997005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457511005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4739997005,"updated_at":"2026-10-08T18:28:42-04:00","requisition_id":"454","title":"Senior Web Experimentation Manager","company_name":"Tailscale","first_published":"2026-10-08T18:28:42-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re looking for a Senior Web Experimentation Manager to own the experimentation program across Tailscale\u0026#39;s highest-traffic website pages, including the homepage, pricing, use-case pages, and paid landing pages.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You\u0026#39;ll set the roadmap, the test design standards, and the decision rules every experiment runs on, and you\u0026#39;ll design and ship the highest-stakes tests yourself. You\u0026#39;ll work closely with web strategy, web development, design, product marketing, and analytics partners, and you\u0026#39;ll coach the people running tests alongside you.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role is for someone who has run an experimentation program, and not only experiments. You know when a test is the right tool and when a change is better shipped without one. You can hold a decision rule when a result is inconvenient, and you treat a flat result as information. Success means a program the rest of the company trusts, results that hold up to scrutiny, and learnings that change what we build next.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own the experimentation roadmap, from taking in ideas across the team to prioritizing them against traffic, expected impact, and cost.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Set and maintain the standards every test runs on, including sizing, statistical power, minimum detectable effect, guardrail metrics, and the rules for shipping, iterating, or stopping a test.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Review test designs before launch and results before they\u0026#39;re shared, so every number we report is one we can stand behind.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design, build, and run the most consequential experiments yourself, particularly on pricing and the homepage.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own the health of our testing platform and measurement with web development and analytics, so tracking works and results reconcile with our analytics data.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain the experiment record as the source of truth for what our website has learned, and turn accumulated results into recommendations for web strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Report program results to marketing leadership: what we learned, what shipped, and what we\u0026#39;re testing next.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Coach contributors across web, design, and marketing on hypothesis quality, test design, and reading results correctly.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6–9 years of experience in conversion optimization, web experimentation, growth marketing, or a related field, including ownership of an experimentation program across multiple pages or products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep experience with a testing platform such as Optimizely, VWO, or a comparable tool, including program-level setup and governance\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong command of experiment statistics, including power and sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, and the risks of peeking and multiple comparisons\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to evaluate a test\u0026#39;s design and validity, and to explain plainly why a result should or shouldn\u0026#39;t be trusted\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort with HTML, CSS, and JavaScript to build and debug client-side variations yourself\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Working proficiency in SQL and an analytics tool such as GA4, enough to validate results independently of the testing platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Sound judgment about when an experiment is the right tool, and when a change is low-risk and reversible enough to ship without one\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Clear writing and communication, with the ability to present results and tradeoffs to senior stakeholders\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience coaching or mentoring others on experimentation, formally or informally\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort working in a remote-first, async environment\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience experimenting on pricing pages, or on pages that route visitors between self-serve and sales-assisted paths\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with B2B SaaS, developer tools, infrastructure, or cybersecurity products\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with server-side or feature-flag testing, or with Bayesian or sequential testing methods\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience moving an experimentation program from one testing platform to another\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with accessibility and web performance considerations in test builds\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building an experiment library that other teams use\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$152,760\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$194,300 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019623005,"name":"Marketing","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4732874005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454065005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4732874005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-ENG-DP","title":"Software Engineer, Networking (Dataplane)","company_name":"Tailscale","first_published":"2026-09-10T15:56:15-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the Dataplane Engineering Team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Contribute to the core client connectivity features of Tailscale by applying a deep understanding of network engineering and software development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evolve and enhance the Tailscale connectivity offerings between clients, subnet routers, exit nodes and other integrations with customer network infrastructure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide architectural insights and resolve escalated customer network issues to fix complex connectivity problems.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with product management and internal engineering to develop integrated network solutions that prioritize scalability and ease of maintenance while ensuring a superior customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design, build, test, and document core Tailscale’s client-side networking software.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advance product features by building upon or merging established industry network protocols with Tailscale\u0026#39;s specific designs and frameworks.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Adopt a security-centric approach to both architecture and coding to guarantee the resilience and safety of networking modules.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evaluate and optimize the performance, reliability, and scale of our software across a wide array of technical platforms and hardware.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide expert consultation and support the customer success teams with critical network escalations within key customer environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Engage actively with the open-source community and contribute to relevant projects.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Significant experience with networking software and diagnosing networking issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Possess a comprehensive grasp of networking engineering, such as routing, VPNs, IP address management, and NAT traversal.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in Go or other low-level languages (e.g. C/C++, Rust), including a strong grasp of concurrent programming and techniques for optimizing performance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with large scale distributed systems is highly desirable\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of low-level OS network stacks is highly desirable\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$218,420\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$302,840 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4732897005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4454065005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4732897005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-ENG-DP","title":"Software Engineer, Networking (Dataplane)","company_name":"Tailscale","first_published":"2026-09-10T15:56:16-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the Dataplane Engineering Team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Contribute to the core client connectivity features of Tailscale by applying a deep understanding of network engineering and software development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evolve and enhance the Tailscale connectivity offerings between clients, subnet routers, exit nodes and other integrations with customer network infrastructure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide architectural insights and resolve escalated customer network issues to fix complex connectivity problems.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with product management and internal engineering to develop integrated network solutions that prioritize scalability and ease of maintenance while ensuring a superior customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Design, build, test, and document core Tailscale’s client-side networking software.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advance product features by building upon or merging established industry network protocols with Tailscale\u0026#39;s specific designs and frameworks.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Adopt a security-centric approach to both architecture and coding to guarantee the resilience and safety of networking modules.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evaluate and optimize the performance, reliability, and scale of our software across a wide array of technical platforms and hardware.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide expert consultation and support the customer success teams with critical network escalations within key customer environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Engage actively with the open-source community and contribute to relevant projects.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Significant experience with networking software and diagnosing networking issues\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Possess a comprehensive grasp of networking engineering, such as routing, VPNs, IP address management, and NAT traversal.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in Go or other low-level languages (e.g. C/C++, Rust), including a strong grasp of concurrent programming and techniques for optimizing performance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with large scale distributed systems is highly desirable\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Knowledge of low-level OS network stacks is highly desirable\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$163,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$226,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4739666005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457331005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4739666005,"updated_at":"2026-10-02T13:58:54-04:00","requisition_id":"441","title":"Software Engineer, Networking (Features)","company_name":"Tailscale","first_published":"2026-10-02T13:58:54-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop the Tailscale product, contributing to both open-source client code and related backend services, with an emphasis on networking features and optimizations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with UX/UI designers and product managers to shape features that enhance networking capabilities\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work as part of a team of engineers to design, build, test, and document core networking software components.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analyze and improve the efficiency, scalability, and stability of networking systems and resources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring a security-first mindset to both design and implementation, ensuring robust and secure networking components.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Proven experience implementing application-layer networking concepts and distributed components, such as proxies, connectors, and overlay routing, to enable seamless connectivity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep knowledge of operating system-level networking internals, including socket programming, routing tables, and packet filtering primitives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Professional experience with Go (Golang)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience designing and maintaining distributed systems, with a solid understanding of concurrency (e.g., multithreading, race conditions, memory management, synchronization primitives) and scalability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with relational databases (e.g., PostgreSQL, MySQL) and writing efficient SQL queries.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills, with the ability to explain complex technical concepts clearly.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong collaborative mindset—you actively give and process constructive feedback and work effectively both independently and as part of a team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Startup-ready flexibility, with the adaptability to pivot and thrive in a fast-paced, dynamic environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$242,540\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$302,840 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4739667005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4457331005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4739667005,"updated_at":"2026-10-02T13:58:57-04:00","requisition_id":"441","title":"Software Engineer, Networking (Features)","company_name":"Tailscale","first_published":"2026-10-02T13:58:57-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop the Tailscale product, contributing to both open-source client code and related backend services, with an emphasis on networking features and optimizations\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with UX/UI designers and product managers to shape features that enhance networking capabilities\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work as part of a team of engineers to design, build, test, and document core networking software components.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analyze and improve the efficiency, scalability, and stability of networking systems and resources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring a security-first mindset to both design and implementation, ensuring robust and secure networking components.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Proven experience implementing application-layer networking concepts and distributed components, such as proxies, connectors, and overlay routing, to enable seamless connectivity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep knowledge of operating system-level networking internals, including socket programming, routing tables, and packet filtering primitives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Professional experience with Go (Golang)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience designing and maintaining distributed systems, with a solid understanding of concurrency (e.g., multithreading, race conditions, memory management, synchronization primitives) and scalability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with relational databases (e.g., PostgreSQL, MySQL) and writing efficient SQL queries.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills, with the ability to explain complex technical concepts clearly.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong collaborative mindset—you actively give and process constructive feedback and work effectively both independently and as part of a team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Startup-ready flexibility, with the adaptability to pivot and thrive in a fast-paced, dynamic environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$181,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$226,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4721713005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448297005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4721713005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-PRS","title":"Software Engineer, Strategic Projects","company_name":"Tailscale","first_published":"2026-08-05T15:04:37-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our Strategic Projects team, reporting to the team\u0026#39;s Engineering Manager and ultimately into our co-founder and Chief Strategy Officer. This team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We move fast from idea to prototype, and we\u0026#39;re growing the side of the team that\u0026#39;s energized by the path from prototype to dependable product. You\u0026#39;ll work shoulder-to-shoulder with product-minded engineers from the moment an idea takes shape, shaping how it\u0026#39;s built so it holds up later, and co-owning the work of making it production-grade: stable, observable, maintainable, and ready for real customer load. You\u0026#39;re the kind of engineer who finds the long tail of development genuinely satisfying, the edge cases, the failure modes, the tests and runbooks, the details that turn a sharp demo into something customers can rely on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You\u0026#39;ll work directly with reference customers on integrations and own the production bar on prototypes that graduate into Tailscale\u0026#39;s product surface area, ensuring the security, review, and operational practices that wrap around agent-generated code actually hold in production.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with product-minded engineers from the start, shaping prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) so the path to production is built in, not bolted on.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Co-own the journey from \u0026quot;works in a demo\u0026quot; to \u0026quot;stable in production\u0026quot;: hardening, error handling, observability, and operational tooling.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own the production bar on prototypes that graduate into Tailscale\u0026#39;s product surface area, including the security and review practices that wrap around agent-generated code.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products, with particular attention to reliability, maintainability, and long-term supportability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Find and close the long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge, that separate a prototype from a dependable product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising the production bar.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Light travel required (\u0026amp;lt;10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Ideal candidates will have experience taking software from prototype to production in startup-like environments. We don\u0026#39;t expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you\u0026#39;d like to keep developing.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Strong at hardening, stabilizing, and maintaining production software; you take satisfaction in detail-oriented work and in closing the long tail of bugs, edge cases, and operational gaps.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Go experience is a must; comfort integrating third-party APIs; basic networking.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with a point of view on where they accelerate work, where they fail, and especially how to wrap them in the review, testing, and security practices that hold the production bar.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning the work of getting something solid into production.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Thrive working independently in a remote environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience operating production services: observability, on-call, incident response, performance and reliability work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Validating prototype code for production use alongside security teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identity infrastructure: IdP platforms, identity sync/provisioning, directory services; authentication protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Building applications on top of LLMs and agentic systems (not just using them as dev tools).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Tailscale itself and with networking challenges in multi-cloud and hybrid deployments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Open source community participation; experience producing publicly-visible artifacts (blog posts, talks, reference implementations).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Python, Rust, and/or TypeScript.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Why You\u0026#39;ll Enjoy Working With Us\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work shoulder-to-shoulder with sharp engineers to turn promising prototypes into products customers depend on.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work alongside reference customers on real integrations rather than abstract roadmaps.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Shape emerging AI connectivity standards and Tailscale\u0026#39;s product strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$218,420\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$302,840 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4146810005,"name":"Strategic Projects","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4721714005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448297005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4721714005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-PRS","title":"Software Engineer, Strategic Projects","company_name":"Tailscale","first_published":"2026-08-05T15:04:38-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Join our Strategic Projects team, reporting to the team\u0026#39;s Engineering Manager and ultimately into our co-founder and Chief Strategy Officer. This team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We move fast from idea to prototype, and we\u0026#39;re growing the side of the team that\u0026#39;s energized by the path from prototype to dependable product. You\u0026#39;ll work shoulder-to-shoulder with product-minded engineers from the moment an idea takes shape, shaping how it\u0026#39;s built so it holds up later, and co-owning the work of making it production-grade: stable, observable, maintainable, and ready for real customer load. You\u0026#39;re the kind of engineer who finds the long tail of development genuinely satisfying, the edge cases, the failure modes, the tests and runbooks, the details that turn a sharp demo into something customers can rely on.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You\u0026#39;ll work directly with reference customers on integrations and own the production bar on prototypes that graduate into Tailscale\u0026#39;s product surface area, ensuring the security, review, and operational practices that wrap around agent-generated code actually hold in production.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with product-minded engineers from the start, shaping prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) so the path to production is built in, not bolted on.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Co-own the journey from \u0026quot;works in a demo\u0026quot; to \u0026quot;stable in production\u0026quot;: hardening, error handling, observability, and operational tooling.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own the production bar on prototypes that graduate into Tailscale\u0026#39;s product surface area, including the security and review practices that wrap around agent-generated code.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products, with particular attention to reliability, maintainability, and long-term supportability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Find and close the long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge, that separate a prototype from a dependable product.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising the production bar.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Light travel required (\u0026amp;lt;10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Ideal candidates will have experience taking software from prototype to production in startup-like environments. We don\u0026#39;t expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you\u0026#39;d like to keep developing.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Strong at hardening, stabilizing, and maintaining production software; you take satisfaction in detail-oriented work and in closing the long tail of bugs, edge cases, and operational gaps.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Go experience is a must; comfort integrating third-party APIs; basic networking.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with a point of view on where they accelerate work, where they fail, and especially how to wrap them in the review, testing, and security practices that hold the production bar.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning the work of getting something solid into production.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Thrive working independently in a remote environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience operating production services: observability, on-call, incident response, performance and reliability work.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Validating prototype code for production use alongside security teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identity infrastructure: IdP platforms, identity sync/provisioning, directory services; authentication protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Building applications on top of LLMs and agentic systems (not just using them as dev tools).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Tailscale itself and with networking challenges in multi-cloud and hybrid deployments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Open source community participation; experience producing publicly-visible artifacts (blog posts, talks, reference implementations).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Python, Rust, and/or TypeScript.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Why You\u0026#39;ll Enjoy Working With Us\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work shoulder-to-shoulder with sharp engineers to turn promising prototypes into products customers depend on.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Work alongside reference customers on real integrations rather than abstract roadmaps.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Shape emerging AI connectivity standards and Tailscale\u0026#39;s product strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$163,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$226,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4146810005,"name":"Strategic Projects","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4715836005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4445330005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4715836005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SEES","title":"Solutions Engineer - Commercial (Expansion Sales)","company_name":"Tailscale","first_published":"2026-07-28T17:19:49-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with AEs to identify, qualify, and close new Commercial customer opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Guide complex multi-stakeholder deals, aligning technical and business objectives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide structured feedback to shape product roadmap and GTM strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable enablement resources, demo environments, and solution blueprints for the SE team.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4/5+ years in a customer-facing SE/SA role within networking or security software\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven experience co-owning pipeline and influencing quota outcomes with Sales\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on architecture experience with AWS, GCP, and/or Azure\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication skills, capable of translating technical features into business value\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience thriving in high-growth or startup environments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$150,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$200,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4715835005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4445330005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4715835005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SEES","title":"Solutions Engineer - Commercial (Expansion Sales)","company_name":"Tailscale","first_published":"2026-07-28T17:19:41-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with AEs to identify, qualify, and close new Commercial customer opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Guide complex multi-stakeholder deals, aligning technical and business objectives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide structured feedback to shape product roadmap and GTM strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable enablement resources, demo environments, and solution blueprints for the SE team.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4/5+ years in a customer-facing SE/SA role within networking or security software\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven experience co-owning pipeline and influencing quota outcomes with Sales\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on architecture experience with AWS, GCP, and/or Azure\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication skills, capable of translating technical features into business value\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience thriving in high-growth or startup environments\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$268,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4722325005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448612005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4722325005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SENB","title":"Solutions Engineer - Commercial (New Business)","company_name":"Tailscale","first_published":"2026-08-07T13:22:02-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with AEs to identify, qualify, and close new Commercial customer opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Guide complex multi-stakeholder deals, aligning technical and business objectives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide structured feedback to shape product roadmap and GTM strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable enablement resources, demo environments, and solution blueprints for the SE team.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4/5+ years in a customer-facing SE/SA role within networking or security software.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven experience co-owning pipeline and influencing quota outcomes with Sales.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on architecture experience with AWS, GCP, and/or Azure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication skills, capable of translating technical features into business value.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience thriving in high-growth or startup environments.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$201,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$268,000 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4722326005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4448612005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4722326005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"EVG-SENB","title":"Solutions Engineer - Commercial (New Business)","company_name":"Tailscale","first_published":"2026-08-07T13:22:03-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with AEs to identify, qualify, and close new Commercial customer opportunities.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Guide complex multi-stakeholder deals, aligning technical and business objectives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide structured feedback to shape product roadmap and GTM strategy.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build scalable enablement resources, demo environments, and solution blueprints for the SE team.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;4/5+ years in a customer-facing SE/SA role within networking or security software.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven experience co-owning pipeline and influencing quota outcomes with Sales.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Hands-on architecture experience with AWS, GCP, and/or Azure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication skills, capable of translating technical features into business value.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience thriving in high-growth or startup environments.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;description\u0026quot;\u0026gt;\u0026lt;p\u0026gt;For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range (OTE)\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$150,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$200,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4744879005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4459691005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4744879005,"updated_at":"2026-10-16T23:00:41-04:00","requisition_id":"EVG-SEAE-US","title":"Strategic Enterprise Account Executive","company_name":"Tailscale","first_published":"2026-10-16T23:00:41-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;About the Role\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Tailscale makes it simple for organizations to securely connect people, devices, and workloads anywhere in the world. As adoption grows within the world’s largest enterprises, we’re launching a Strategic Sales team to support our next stage of growth.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies. You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and connecting customer priorities with Tailscale’s capabilities.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll help define how we win in this market - developing outbound strategies, testing new approaches, and creating a playbook for future growth. Reporting to the Director of Strategic Sales, you’ll join a small, highly collaborative team and partner closely with executive leadership and teams across the business.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;Key Responsibilities\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own account strategy: Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Create pipeline: Drive personalized outbound prospecting, partnering with SDRs and Marketing on coordinated account-based campaigns\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead complex deals: Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build executive relationships: Earn trust with CIOs, CISOs, CTOs, and senior technical and business leaders while developing champions across the organization\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring the right team together: Partner with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Shape the playbook: Test approaches, share what works, and bring customer feedback to teams shaping Tailscale’s product and enterprise strategy\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Execute with discipline: Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;What We Are Looking For\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of success as a top-performing enterprise or strategic seller in early stage, high-growth environments\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven success selling to organizations with 10,000+ employees and closing complex six and seven-figure SaaS deals\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven track record of consistently achieving or exceeding annual performance targets, with demonstrated YoY growth and sustained results\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;The ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong business judgment, clear written and verbal communication, and a collaborative, accountable approach\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort with ambiguity and enthusiasm for building a sales motion while carrying a quota\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated commitment to CRM hygiene, including accurate opportunity management, pipeline tracking, and forecast reliability\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Preferred experience:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Serving as an early sales hire or helping build a new enterprise sales motion\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Candidates must have strong technical acumen. Background in selling infrastructure, networking, cybersecurity, developer tools, or cloud software is a bonus\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;You’ll Thrive Here If You…\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Enjoy building from the ground up - creating account strategies, testing approaches, and shaping a playbook as you go\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Love opening doors and winning complex enterprise deals through executive relationships, technical curiosity, and teamwork\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Are energized by ambiguity and take initiative to create structure and momentum\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring the same focus and discipline to building pipeline as you do to navigating complex negotiations and closing strategic deals\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Want to help define how Tailscale wins and grows its largest enterprise customers\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$350,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$350,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019621005,"name":"Sales","child_ids":[],"parent_id":null}],"offices":[{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4730717005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4452023005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Contract","value_type":"single_select"}],"id":4730717005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"412","title":"Talent Acquisition Partner (Contract)","company_name":"Tailscale","first_published":"2026-09-03T11:05:55-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;p\u0026gt;We’re hiring multiple experienced Talent Acquisition Partners to join Tailscale on an initial 6-month contract basis, with the potential to extend and/or convert to full-time roles based on business needs and performance.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;These roles will support different parts of the organization, with individual assignments focused on \u0026lt;strong\u0026gt;Engineering, Product \u0026amp;amp; Design (EPD), Go-to-Market \u0026amp;amp; G\u0026amp;amp;A, or a broader cross-functional portfolio spanning multiple organizations\u0026lt;/strong\u0026gt;. During the application process, candidates will have the opportunity to indicate where they have the most experience and where they would prefer to focus.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll operate as a fully integrated member of our Talent Acquisition team, owning searches from intake through offer and partnering with hiring managers and business leaders to develop thoughtful recruiting strategies, navigate competitive talent markets, and deliver an exceptional candidate experience.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale operates in a highly technical, fast-moving environment, so we’re looking for recruiters who are curious, adaptable, and comfortable learning new areas quickly. Whether your background is primarily technical, commercial/corporate, or broad-based, you’ll bring strong recruiting craft, market intelligence, data, and sound judgment to help hiring teams make great decisions while maintaining a consistently high hiring bar.\u0026lt;/p\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Lead Full-Cycle Recruiting\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own complex searches from intake through offer across EPD, GTM, G\u0026amp;amp;A, or a combination of functions based on assigned business needs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with hiring managers to define candidate profiles, develop recruiting strategies, and establish effective interview processes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage multiple searches while maintaining a high bar for quality, speed, and candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead candidate assessment, offer strategy, negotiation, and closing in partnership with hiring teams.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Develop Talent \u0026amp;amp; Sourcing Strategies\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build recruiting and sourcing strategies based on business priorities, role requirements, talent availability, and market conditions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Sourcers on targeted searches and talent mapping while sourcing directly as needed and maintaining accountability for pipeline health.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Use recruiting data, candidate feedback, and market intelligence to evaluate search performance and adjust strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify alternative talent pools, companies, locations, or profiles when searches require a different approach.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Advise \u0026amp;amp; Influence Hiring Teams\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build trusted relationships with hiring managers and business leaders and serve as a consultative recruiting partner.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide actionable insights on talent markets, candidate expectations, hiring timelines, and potential tradeoffs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Constructively challenge assumptions and create accountability around interview quality, timely feedback, decision-making, and candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactively identify hiring risks and partner with TA leadership when broader support or escalation is needed.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Recruit Across Your Area of Focus\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Depending on your background and assignment, you may support:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Engineering, Product \u0026amp;amp; Design:\u0026lt;/strong\u0026gt; including highly technical or specialized Engineering, Product, Design, and leadership searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;GTM \u0026amp;amp; G\u0026amp;amp;A:\u0026lt;/strong\u0026gt; including Sales, Customer Success, Marketing, Revenue Operations, Partnerships, Finance, Legal, People, and other business functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cross-Functional / All Orgs:\u0026lt;/strong\u0026gt; a mix of technical and non-technical hiring across the company as priorities evolve.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Partner Across Talent Acquisition\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Collaborate closely with Sourcers, Coordinators, TA Operations, fellow TA Partners, and TA leadership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Share market insights, sourcing approaches, and recruiting best practices across the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to recruiting initiatives and process improvements that strengthen hiring effectiveness and scalability.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ years of full-cycle recruiting experience, ideally within high-growth SaaS, cloud, infrastructure, developer tools, cybersecurity, or other technology environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success recruiting within EPD, GTM/G\u0026amp;amp;A, or across multiple functions and levels.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong full-cycle recruiting skills across intake, sourcing, candidate assessment, stakeholder management, offer negotiation, and closing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing recruiting and sourcing strategies for complex or highly competitive searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to quickly understand unfamiliar technical or business roles and translate hiring needs into effective recruiting strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to partner with hiring managers and business leaders as a trusted advisor, using strong judgment to influence decisions, challenge assumptions, and maintain accountability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort using recruiting data and market intelligence to diagnose challenges and improve hiring outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication, organization, and prioritization skills with the ability to independently manage multiple searches in a fast-moving, distributed environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting across multiple areas of the business, including both technical and non-technical functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting highly technical talent within infrastructure, networking, security, distributed systems, developer tools, cloud, or adjacent areas.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting Sales and broader GTM talent across different functions, levels, or sales motions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with Sourcers on sophisticated strategies for difficult-to-fill roles.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using talent mapping, market intelligence, recruiting data, AI, or emerging recruiting technologies to improve hiring outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Note:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;this is a contract position and is not eligible for the full-time, exempt benefits listed below.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$67\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$81 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4037251005,"name":"People \u0026 Talent","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4728969005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4452023005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Contract","value_type":"single_select"}],"id":4728969005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"412","title":"Talent Acquisition Partner (Contract)","company_name":"Tailscale","first_published":"2026-09-03T11:05:53-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;p\u0026gt;We’re hiring multiple experienced Talent Acquisition Partners to join Tailscale on an initial 6-month contract basis, with the potential to extend and/or convert to full-time roles based on business needs and performance.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;These roles will support different parts of the organization, with individual assignments focused on \u0026lt;strong\u0026gt;Engineering, Product \u0026amp;amp; Design (EPD), Go-to-Market \u0026amp;amp; G\u0026amp;amp;A, or a broader cross-functional portfolio spanning multiple organizations\u0026lt;/strong\u0026gt;. During the application process, candidates will have the opportunity to indicate where they have the most experience and where they would prefer to focus.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll operate as a fully integrated member of our Talent Acquisition team, owning searches from intake through offer and partnering with hiring managers and business leaders to develop thoughtful recruiting strategies, navigate competitive talent markets, and deliver an exceptional candidate experience.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale operates in a highly technical, fast-moving environment, so we’re looking for recruiters who are curious, adaptable, and comfortable learning new areas quickly. Whether your background is primarily technical, commercial/corporate, or broad-based, you’ll bring strong recruiting craft, market intelligence, data, and sound judgment to help hiring teams make great decisions while maintaining a consistently high hiring bar.\u0026lt;/p\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Lead Full-Cycle Recruiting\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own complex searches from intake through offer across EPD, GTM, G\u0026amp;amp;A, or a combination of functions based on assigned business needs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with hiring managers to define candidate profiles, develop recruiting strategies, and establish effective interview processes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage multiple searches while maintaining a high bar for quality, speed, and candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead candidate assessment, offer strategy, negotiation, and closing in partnership with hiring teams.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Develop Talent \u0026amp;amp; Sourcing Strategies\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build recruiting and sourcing strategies based on business priorities, role requirements, talent availability, and market conditions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Sourcers on targeted searches and talent mapping while sourcing directly as needed and maintaining accountability for pipeline health.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Use recruiting data, candidate feedback, and market intelligence to evaluate search performance and adjust strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify alternative talent pools, companies, locations, or profiles when searches require a different approach.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Advise \u0026amp;amp; Influence Hiring Teams\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Build trusted relationships with hiring managers and business leaders and serve as a consultative recruiting partner.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Provide actionable insights on talent markets, candidate expectations, hiring timelines, and potential tradeoffs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Constructively challenge assumptions and create accountability around interview quality, timely feedback, decision-making, and candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proactively identify hiring risks and partner with TA leadership when broader support or escalation is needed.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Recruit Across Your Area of Focus\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;Depending on your background and assignment, you may support:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Engineering, Product \u0026amp;amp; Design:\u0026lt;/strong\u0026gt; including highly technical or specialized Engineering, Product, Design, and leadership searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;GTM \u0026amp;amp; G\u0026amp;amp;A:\u0026lt;/strong\u0026gt; including Sales, Customer Success, Marketing, Revenue Operations, Partnerships, Finance, Legal, People, and other business functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cross-Functional / All Orgs:\u0026lt;/strong\u0026gt; a mix of technical and non-technical hiring across the company as priorities evolve.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Partner Across Talent Acquisition\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Collaborate closely with Sourcers, Coordinators, TA Operations, fellow TA Partners, and TA leadership.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Share market insights, sourcing approaches, and recruiting best practices across the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to recruiting initiatives and process improvements that strengthen hiring effectiveness and scalability.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;6+ years of full-cycle recruiting experience, ideally within high-growth SaaS, cloud, infrastructure, developer tools, cybersecurity, or other technology environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success recruiting within EPD, GTM/G\u0026amp;amp;A, or across multiple functions and levels.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong full-cycle recruiting skills across intake, sourcing, candidate assessment, stakeholder management, offer negotiation, and closing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing recruiting and sourcing strategies for complex or highly competitive searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to quickly understand unfamiliar technical or business roles and translate hiring needs into effective recruiting strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to partner with hiring managers and business leaders as a trusted advisor, using strong judgment to influence decisions, challenge assumptions, and maintain accountability.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort using recruiting data and market intelligence to diagnose challenges and improve hiring outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication, organization, and prioritization skills with the ability to independently manage multiple searches in a fast-moving, distributed environment.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting across multiple areas of the business, including both technical and non-technical functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting highly technical talent within infrastructure, networking, security, distributed systems, developer tools, cloud, or adjacent areas.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience recruiting Sales and broader GTM talent across different functions, levels, or sales motions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience partnering with Sourcers on sophisticated strategies for difficult-to-fill roles.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using talent mapping, market intelligence, recruiting data, AI, or emerging recruiting technologies to improve hiring outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Note:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;this is a contract position and is not eligible for the full-time, exempt benefits listed below.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$90\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$109 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4037251005,"name":"People \u0026 Talent","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4731033005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4453062005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Contract","value_type":"single_select"}],"id":4731033005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"414","title":"Talent Acquisition Sourcer (Contract)","company_name":"Tailscale","first_published":"2026-09-04T10:47:11-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for an experienced Talent Acquisition Sourcer to help identify and engage exceptional talent as Tailscale continues to scale. This is initially a 6-month contract position with the potential to extend and/or convert to a full-time role based on business needs and performance.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll operate as a fully integrated member of our Talent Acquisition team, partnering with Talent Acquisition Partners and hiring teams to build high-quality pipelines across Engineering, Product, Design, GTM, G\u0026amp;amp;A, and other business-critical searches.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for someone who is curious, resourceful, and creative; can quickly understand new roles and talent markets; and is comfortable going beyond traditional sourcing methods to find and engage exceptional people.\u0026lt;/p\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Build \u0026amp;amp; Execute Sourcing Strategies\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to understand candidate profiles, hiring priorities, and sourcing needs across the company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and execute targeted sourcing strategies across Engineering, Product, Design, GTM, G\u0026amp;amp;A, and other functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and engage passive talent using a range of sourcing channels, research methods, communities, networks, and creative approaches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage multiple searches and adjust sourcing strategies based on pipeline performance, candidate feedback, and evolving priorities.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Source Technical \u0026amp;amp; Specialized Talent\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop a strong understanding of Tailscale’s product, technology, business, and culture to effectively identify candidates who may thrive here.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate technical and specialized role requirements into effective searches in partnership with Talent Acquisition Partners and hiring teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Research relevant companies, technologies, communities, and talent pools to identify candidates beyond traditional sources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build knowledge of talent markets relevant to Tailscale, including infrastructure, networking, security, developer tools, cloud technologies, and other functional areas.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Use Data \u0026amp;amp; Market Intelligence\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Bring comfort with sourcing data and market insights to evaluate pipeline health, identify search challenges, and improve sourcing outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct talent research and market mapping across relevant companies, locations, candidate profiles, and competitive talent pools.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Surface actionable insights on candidate availability, market trends, and search constraints to Talent Acquisition Partners.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build reusable talent maps and research that can support current and future hiring needs.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Build Inclusive Talent Pipelines\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Incorporate inclusive sourcing practices into search strategies from the outset.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify talent across a broad range of backgrounds, experiences, communities, and career paths.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Explore new networks, communities, and sourcing channels that expand access to qualified talent.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to broaden search approaches and improve candidate representation where appropriate.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Engage Exceptional Talent\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Create thoughtful, personalized outreach that communicates why Tailscale and the specific opportunity may be compelling.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build authentic relationships with passive candidates and assess interest, motivation, experience, and potential alignment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to ensure seamless candidate handoffs and a consistent candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Represent Tailscale thoughtfully and authentically in every interaction with prospective talent.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Partner Across Talent Acquisition\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with Talent Acquisition Partners, Sourcers, Operations, and hiring teams on search strategy, candidate calibration, and pipeline development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participate in sourcing jams and share sourcing techniques, talent pools, market observations, and search learnings across the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support high-priority or specialized searches as needed, adapting quickly as hiring priorities evolve.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Operations to improve sourcing tools, workflows, data quality, automation, and AI-enabled practices.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;3+ years of talent sourcing and/or recruiting experience, ideally within high-growth technology companies or similarly competitive talent environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing technical talent and supporting searches across multiple functions such as Engineering, Product, Design, GTM, or G\u0026amp;amp;A.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to quickly understand complex or unfamiliar roles and translate candidate requirements into effective sourcing strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong research skills and experience using sourcing techniques beyond basic keyword, title, or traditional platform searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong passive candidate engagement and communication skills, including the ability to create thoughtful, personalized outreach.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong organizational and analytical skills, with the ability to manage multiple searches and use sourcing data to evaluate pipeline effectiveness.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborative and adaptable working style, with experience using sourcing platforms, ATS technology, and an interest in AI, automation, and emerging sourcing tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing within a highly technical startup, developer tools, infrastructure, networking, security, cloud, or similar environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience identifying technical talent through GitHub, open-source or technical communities, and other channels beyond traditional recruiting platforms.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing across technical and non-technical functions, geographies, or globally distributed teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting difficult-to-fill, leadership, or confidential searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building talent maps, conducting competitive research, or contributing to collaborative sourcing sessions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of building broad candidate pipelines and finding strong talent through creative research, persistence, and thoughtful engagement.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Note: \u0026lt;/strong\u0026gt;this is a contract position and is not eligible for the full-time, exempt benefits listed below.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$65\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$71 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4037251005,"name":"People \u0026 Talent","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4731178005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4453062005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Contract","value_type":"single_select"}],"id":4731178005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"414","title":"Talent Acquisition Sourcer (Contract)","company_name":"Tailscale","first_published":"2026-09-04T10:47:13-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for an experienced Talent Acquisition Sourcer to help identify and engage exceptional talent as Tailscale continues to scale. This is initially a 6-month contract position with the potential to extend and/or convert to a full-time role based on business needs and performance.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll operate as a fully integrated member of our Talent Acquisition team, partnering with Talent Acquisition Partners and hiring teams to build high-quality pipelines across Engineering, Product, Design, GTM, G\u0026amp;amp;A, and other business-critical searches.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re looking for someone who is curious, resourceful, and creative; can quickly understand new roles and talent markets; and is comfortable going beyond traditional sourcing methods to find and engage exceptional people.\u0026lt;/p\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Build \u0026amp;amp; Execute Sourcing Strategies\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to understand candidate profiles, hiring priorities, and sourcing needs across the company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and execute targeted sourcing strategies across Engineering, Product, Design, GTM, G\u0026amp;amp;A, and other functions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify and engage passive talent using a range of sourcing channels, research methods, communities, networks, and creative approaches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage multiple searches and adjust sourcing strategies based on pipeline performance, candidate feedback, and evolving priorities.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Source Technical \u0026amp;amp; Specialized Talent\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop a strong understanding of Tailscale’s product, technology, business, and culture to effectively identify candidates who may thrive here.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate technical and specialized role requirements into effective searches in partnership with Talent Acquisition Partners and hiring teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Research relevant companies, technologies, communities, and talent pools to identify candidates beyond traditional sources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build knowledge of talent markets relevant to Tailscale, including infrastructure, networking, security, developer tools, cloud technologies, and other functional areas.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Use Data \u0026amp;amp; Market Intelligence\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Bring comfort with sourcing data and market insights to evaluate pipeline health, identify search challenges, and improve sourcing outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct talent research and market mapping across relevant companies, locations, candidate profiles, and competitive talent pools.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Surface actionable insights on candidate availability, market trends, and search constraints to Talent Acquisition Partners.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build reusable talent maps and research that can support current and future hiring needs.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Build Inclusive Talent Pipelines\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Incorporate inclusive sourcing practices into search strategies from the outset.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Identify talent across a broad range of backgrounds, experiences, communities, and career paths.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Explore new networks, communities, and sourcing channels that expand access to qualified talent.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to broaden search approaches and improve candidate representation where appropriate.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Engage Exceptional Talent\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Create thoughtful, personalized outreach that communicates why Tailscale and the specific opportunity may be compelling.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Build authentic relationships with passive candidates and assess interest, motivation, experience, and potential alignment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Partners to ensure seamless candidate handoffs and a consistent candidate experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Represent Tailscale thoughtfully and authentically in every interaction with prospective talent.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Partner Across Talent Acquisition\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with Talent Acquisition Partners, Sourcers, Operations, and hiring teams on search strategy, candidate calibration, and pipeline development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Participate in sourcing jams and share sourcing techniques, talent pools, market observations, and search learnings across the team.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Support high-priority or specialized searches as needed, adapting quickly as hiring priorities evolve.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Talent Acquisition Operations to improve sourcing tools, workflows, data quality, automation, and AI-enabled practices.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;3+ years of talent sourcing and/or recruiting experience, ideally within high-growth technology companies or similarly competitive talent environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing technical talent and supporting searches across multiple functions such as Engineering, Product, Design, GTM, or G\u0026amp;amp;A.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to quickly understand complex or unfamiliar roles and translate candidate requirements into effective sourcing strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong research skills and experience using sourcing techniques beyond basic keyword, title, or traditional platform searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong passive candidate engagement and communication skills, including the ability to create thoughtful, personalized outreach.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong organizational and analytical skills, with the ability to manage multiple searches and use sourcing data to evaluate pipeline effectiveness.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborative and adaptable working style, with experience using sourcing platforms, ATS technology, and an interest in AI, automation, and emerging sourcing tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h2\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/h2\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing within a highly technical startup, developer tools, infrastructure, networking, security, cloud, or similar environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience identifying technical talent through GitHub, open-source or technical communities, and other channels beyond traditional recruiting platforms.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience sourcing across technical and non-technical functions, geographies, or globally distributed teams.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting difficult-to-fill, leadership, or confidential searches.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building talent maps, conducting competitive research, or contributing to collaborative sourcing sessions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A track record of building broad candidate pipelines and finding strong talent through creative research, persistence, and thoughtful engagement.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Note: \u0026lt;/strong\u0026gt;this is a contract position and is not eligible for the full-time, exempt benefits listed below.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$49\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$53 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4037251005,"name":"People \u0026 Talent","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4710785005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4443073005,"location":{"name":"Remote (United States)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4710785005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"341","title":"Windows Engineer","company_name":"Tailscale","first_published":"2026-06-30T13:59:03-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented and motivated full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop the Tailscale product, contributing to client code and backend services. The client code is a mix of C#, XAML, and Go. Prior Go expertise is not a requirement.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring a special focus on our Windows platform, building and maintaining our Windows client using the modern WinUI/Windows App SDK stack, while contributing to common code that supports macOS, mobile, and other core client platforms.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Implement support for the latest Windows platform features while maintaining compatibility with a subset of older versions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and optimize product features on Windows, with a focus on UI components and platform integration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to common, cross-platform Tailscale code\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Four or more years of experience in software development\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of software development principles, capabilities, and limitations of the Windows platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in C# and modern native UI frameworks (WinUI/UWP/WPF)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with general networking concepts - DNS, VPNs, IP Networking, routing, etc.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience with WinUI 3 and Windows App SDK\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing native Windows applications and services\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Windows networking stack and Windows Filtering Platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Windows security model, session isolation, access tokens and related concepts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in Go\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;US Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$143,000\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$179,000 USD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null},{"absolute_url":"https://job-boards.greenhouse.io/tailscale/jobs/4710781005","data_compliance":[{"type":"gdpr","requires_consent":false,"requires_processing_consent":false,"requires_retention_consent":false,"retention_period":null,"demographic_data_consent_applies":false}],"internal_job_id":4443073005,"location":{"name":"Remote (Canada)"},"metadata":[{"id":4536497005,"name":"Employment Type","value":"Full-time","value_type":"single_select"}],"id":4710781005,"updated_at":"2026-09-29T20:38:27-04:00","requisition_id":"341","title":"Windows Engineer","company_name":"Tailscale","first_published":"2026-06-30T13:59:02-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;Thank you for considering Tailscale. If this job description resonates with you, please apply.\u0026amp;nbsp;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. \u0026lt;/em\u0026gt;\u0026lt;em data-stringify-type=\u0026quot;italic\u0026quot;\u0026gt;We encourage you to help us break that statistic!\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About Tailscale\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We\u0026#39;re building a future for the Internet that\u0026#39;s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we\u0026#39;re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;About the Role\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We’re seeking a talented and motivated full-time Software Engineer to join our growing team. You will work as part of the engineering team to:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Develop the Tailscale product, contributing to client code and backend services. The client code is a mix of C#, XAML, and Go. Prior Go expertise is not a requirement.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bring a special focus on our Windows platform, building and maintaining our Windows client using the modern WinUI/Windows App SDK stack, while contributing to common code that supports macOS, mobile, and other core client platforms.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.\u0026lt;/p\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Key Responsibilities\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Implement support for the latest Windows platform features while maintaining compatibility with a subset of older versions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and optimize product features on Windows, with a focus on UI components and platform integration\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to common, cross-platform Tailscale code\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;What We Are Looking For\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Four or more years of experience in software development\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong understanding of software development principles, capabilities, and limitations of the Windows platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in C# and modern native UI frameworks (WinUI/UWP/WPF)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with general networking concepts - DNS, VPNs, IP Networking, routing, etc.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to give and process constructive feedback, as well as work independently\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Flexibility to adjust to the dynamic nature of a startup\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;span style=\u0026quot;font-size: 12pt;\u0026quot;\u0026gt;\u0026lt;strong\u0026gt;Nice to Have\u0026lt;/strong\u0026gt;\u0026lt;/span\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Experience with WinUI 3 and Windows App SDK\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience developing native Windows applications and services\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Windows networking stack and Windows Filtering Platform\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Windows security model, session isolation, access tokens and related concepts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in Go\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale\u0026#39;s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire\u0026#39;s base salary. Individual offers may vary based on experience and skill set.\u0026lt;/p\u0026gt;\u0026lt;div class=\u0026quot;content-pay-transparency\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;pay-input\u0026quot;\u0026gt;\u0026lt;div class=\u0026quot;title\u0026quot;\u0026gt;CAN Pay Range\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;pay-range\u0026quot;\u0026gt;\u0026lt;span\u0026gt;$191,620\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;divider\u0026quot;\u0026gt;\u0026amp;mdash;\u0026lt;/span\u0026gt;\u0026lt;span\u0026gt;$239,860 CAD\u0026lt;/span\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;div class=\u0026quot;content-conclusion\u0026quot;\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What We Offer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;An inclusive, flexible environment where you can be your authentic self.\u0026lt;/strong\u0026gt; We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A competitive total compensation package.\u0026lt;/strong\u0026gt; This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Comprehensive group benefits with no waiting period. \u0026lt;/strong\u0026gt;Take advantage of coverage for health, vision, dental, and more for you and your family!\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Remote first company\u0026lt;/strong\u0026gt;—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Employer-funded retirement contributions. \u0026lt;/strong\u0026gt;Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Connect with other Tailscalars IRL. \u0026lt;/strong\u0026gt;Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Support for your personal and professional development.\u0026lt;/strong\u0026gt; Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid time off and a healthy work-life integration.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;A build-your-own home office setup. \u0026lt;/strong\u0026gt;You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Paid parental leave program\u0026lt;/strong\u0026gt;. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;em\u0026gt;Please be aware that legitimate emails from Tailscale\u0026#39;s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit \u0026lt;a href=\u0026quot;https://tailscale.com/scam-awareness\u0026quot;\u0026gt;https://tailscale.com/scam-awareness\u0026lt;/a\u0026gt;.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;","departments":[{"id":4019620005,"name":"Engineering","child_ids":[],"parent_id":null}],"offices":[{"id":4008467005,"name":"Remote (Canada)","location":"Canada","child_ids":[],"parent_id":null},{"id":4008466005,"name":"Remote (United States) ","location":"United States","child_ids":[],"parent_id":null}],"ai_disclaimer":null,"include_ai_disclaimer":null,"ai_opt_out_request_url":null}],"meta":{"total":62}}