{"jobs":[{"absolute_url":"https://job-boards.greenhouse.io/contactmonkey/jobs/4685951006","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":4549972006,"location":{"name":"Toronto "},"metadata":null,"id":4685951006,"updated_at":"2026-06-03T13:41:45-04:00","requisition_id":"156","title":"Customer Success Manager – Mid-Market (Spanish Fluency)","company_name":"ContactMonkey","first_published":"2026-06-03T12:00:59-04:00","language":"en","application_deadline":null,"content":"\u0026lt;p\u0026gt;Hey there! We’re ContactMonkey 👋\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the job\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Customer Success Manager, Mid-Market at ContactMonkey, you’ll be responsible for managing a portfolio of mid-market accounts and ensuring their continued success with the platform. Your primary focus will be to onboard, manage, and retain customers, while also supporting expansion across your book of business. This role directly impacts customer satisfaction, adoption, retention, and overall revenue growth at ContactMonkey.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll work closely with Sales, Product, and Support to ensure the customer’s voice is represented across the organization. You’re comfortable uncovering customer needs and identifying growth opportunities, supporting upsell and cross-sell conversations in a way that delivers value to the customer.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our Customer Success team is looking for a motivated individual with 2+ years of customer-facing experience and a strong foundation in relationship-building to join our growing team. In this role, you’ll own customer relationships, drive product adoption and engagement, increase customer value over time, and act as a trusted partner throughout the customer lifecycle.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The ideal candidate is collaborative and eager to learn, with the ability to work cross-functionally to support customer outcomes. If you’re proactive, curious, and excited to grow your career in Customer Success, this role could be a great fit.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role requires fluency in Spanish, as you will support a portion of Spanish-speaking customers across your portfolio.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Your impact\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own and manage a portfolio of mid-market accounts, ensuring strong adoption, engagement, and customer satisfaction\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Onboard new customers through training of best practices\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive retention across your book of business while identifying opportunities for expansion and growth\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate closely with Sales, Product, and Support to deliver a seamless customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Facilitate the customer’s product journey through support touch-points; including business reviews, identifying upsell/cross sell opportunities and providing recommendations on best practices\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct client outreach and manage customer expectations to drive customer retention and growth\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Utilize customer feedback and data to identify potential risk and use your curiosity and business acumen to mitigate churn\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About you\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;2+ years experience in a customer relationship management role - preferably in a B2B SaaS environment\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven track record of meeting and exceeding retention targets across a book of business\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven track record of driving growth revenue through increased platform adoption and broader product usage across customer accounts\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Native or professional fluency in Spanish and English is required. You will be responsible for handling renewals, onboarding, and day-to-day success metrics for our Spanish-speaking portfolio\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience delivering software training with the ability to convey information in a clear, digestible manner\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to solve problems effectively and timely\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong project management and detail oriented organizational skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent communication and teamwork skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Ability to work independently and collaboratively\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How you can stand out\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You are a problem solver that doesn’t shy away from a challenging situation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You are enthusiastic about building lasting partnerships and deliver a customer-first focused mindset\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have an aptitude for technology and are eager to learn and upskill\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What we bring to the table\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏥 100% employer-paid benefits + a Health Spending Account from day one\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🌎 Work from anywhere in the world for up to 4 weeks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💰 Stock option plan—own a piece of our success\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💲 RRSP Group Savings Plan to plan for your future\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏝 Generous vacation package to recharge and relax\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;📚 Personal development budget to fuel your growth\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🧖 One personal day + two volunteering days to give back\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🎂 Your Birthday off—celebrate on us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🍎 Five health days per year to stay at your best\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Compensation \u0026amp;amp; Work Details\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The base salary range for this role is $60,000 - $80,000 CAD. In addition to base salary, this role includes a variable compensation component. Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re always happy to answer questions about compensation throughout the hiring process.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a backfill position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x/week to promote collaboration.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ranked by the Globe \u0026amp;amp; Mail \u0026lt;/strong\u0026gt;as one of Canada’s fastest-growing companies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™\u0026lt;/strong\u0026gt; awards for revenue growth over the \u0026lt;strong\u0026gt;past four years\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ \u0026lt;/strong\u0026gt;as one of the fastest-growing companies in North America\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Raised $55 million Series A financing\u0026lt;/strong\u0026gt; in 2023\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Diversity is our strength\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;AI Disclosure:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.\u0026lt;/p\u0026gt;","departments":[{"id":4009932006,"name":"Customer Success ","child_ids":[],"parent_id":null}],"offices":[{"id":4005312006,"name":"Toronto","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/contactmonkey/jobs/4686097006","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":4550056006,"location":{"name":"Toronto "},"metadata":null,"id":4686097006,"updated_at":"2026-06-02T13:48:33-04:00","requisition_id":"157","title":"GTM Engineer, Revenue Operations","company_name":"ContactMonkey","first_published":"2026-06-02T13:48:01-04:00","language":"en","application_deadline":null,"content":"\u0026lt;p\u0026gt;Hey there! We’re ContactMonkey 👋\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the job - GTM Engineer, Revenue Operations\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are looking for a GTM Engineer, Revenue Operations to join our Revenue Operations team and help build the next generation of ContactMonkey’s revenue engine.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You will sit at the intersection of RevOps, Sales, Marketing, Data, and AI automation. You will own core GTM systems, build scalable workflows, improve lead and account distribution, support forecasting and stage discipline, and turn ideas into working systems that help our revenue teams generate, manage, and convert pipeline more effectively.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You will be the primary owner of Salesforce, HubSpot, and Clay, and you will partner closely with the VP of RevOps on our analytics stack, including AWS AppFlow, Athena, and QuickSight. You will also help expand our AI personalization initiatives and enable the sales team through better process, data, Gong insights, and MEDDIC adoption.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The ideal candidate is a builder-operator: technically curious, commercially sharp, automation-obsessed, and comfortable using AI and low-code/no-code tools to ship practical solutions quickly.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Your impact\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Own and evolve the GTM technology stack\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will own the day-to-day health, architecture, and continuous improvement of Salesforce and HubSpot. This includes object design, fields, workflows, automations, integrations, data quality, permissions, campaign and lifecycle tracking, and the handoffs between Marketing, Sales, Customer Success, and Finance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will also own ContactMonkey’s Clay instance and use it to build high-impact automation across enrichment, routing, research, personalization, scoring, and outbound/inbound workflows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will evaluate, implement, and optimize GTM tools that improve speed, data accuracy, rep productivity, and revenue visibility.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Build AI-powered revenue automation\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will design and ship AI-enabled workflows that reduce manual work and improve GTM execution. This may include account research, persona mapping, lead enrichment, territory/account matching, inbound routing, outbound personalization, follow-up automation, and sales-assist workflows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will use AI-assisted development, automation tools, and “vibe coding” practices to prototype and operationalize new ideas quickly, while maintaining appropriate controls, documentation, and data hygiene.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Own lead and account distribution\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will manage and improve the processes that determine how leads, accounts, and opportunities are assigned across the GTM team. This includes routing logic, ownership rules, round robins, territory mapping, SLA tracking, source attribution, deduplication, and exception handling.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will partner with Sales and Marketing leaders to make sure the right records get to the right people at the right time, with the right context.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Partner with Marketing on demand gen operations\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will work closely with the Marketing team to optimize inbound lead flow, including the routing and speed-to-lead logic in Chili Piper, so that high-intent prospects reach the right reps quickly and reliably.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will help operationalize demand and intent tools like G2, turning buyer signals into actionable workflows that prioritize and surface the right accounts and leads.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will build the workflows, data, and reporting needed to understand channel performance, giving Marketing and RevOps clear visibility into where pipeline and revenue are coming from.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will support initiatives related to LLM discoverability, helping ensure ContactMonkey is well represented and easily found across AI-driven search and discovery experiences.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Support analytics, forecasting, and revenue visibility\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will partner with the VP of RevOps to improve ContactMonkey’s revenue analytics foundation across AWS AppFlow, Athena, QuickSight, Salesforce, HubSpot, and related data sources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will help maintain clean, reliable data flows and build dashboards or reporting layers that give leaders visibility into pipeline creation, conversion, stage progression, forecast health, rep productivity, lead performance, campaign impact, and GTM efficiency.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Strengthen sales process and methodology\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will support forecasting, stage management, pipeline hygiene, and MEDDIC adoption. This includes building the fields, validation rules, workflows, reporting, and enablement assets that help sales leaders inspect deals consistently and coach reps effectively.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will help ensure Salesforce reflects the reality of the deal cycle, not just administrative updates.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Build Tools to Support Enablement through Gong and GTM insights\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You will build the tools and systems that allow Sales leadership and Enablement to effectively use Gong insights to improve rep performance, messaging, discovery, objection handling, MEDDIC adherence, and stage progression.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You will design and implement the practical enablement workflows, dashboards, trackers, and feedback loops based on call and deal insights, ensuring the right tools are in place for the enablement team.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About you\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Experience\u0026lt;/strong\u0026gt;: 5+ years in Revenue Operations, Sales/Marketing Operations, or GTM Engineering.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;GTM Systems Expertise\u0026lt;/strong\u0026gt;: Hands-on experience with Salesforce and HubSpot, covering architecture, process design, data quality, and reporting.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Automation/AI:\u0026lt;/strong\u0026gt; Experience with Clay (or the ability to master it) for building AI-powered automations, including enrichment, personalization, and CRM writeback. Proven ability with other automation tools (e.g., Zapier, Salesforce Flow).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Data Fluency\u0026lt;/strong\u0026gt;: Comfortable with data schemas, SQL, troubleshooting, and partnering on analytics infrastructure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;GTM Acumen\u0026lt;/strong\u0026gt;: Deep understanding of B2B SaaS GTM motions, including pipeline generation, forecasting, and sales methodology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Mindset\u0026lt;/strong\u0026gt;: A detail-oriented, commercially sharp builder-operator who prioritizes speed, iteration, and clear communication with technical and non-technical stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How you can stand out\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Salesforce certifications (e.g., Administrator, Platform App Builder).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with AWS AppFlow, Athena, QuickSight, S3, or similar data/BI infrastructure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience supporting MEDDIC or another enterprise sales methodology inside Salesforce.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with Gong administration, trackers, call analysis, enablement workflows, or sales coaching insights.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with AI personalization at scale, outbound automation, intent-based routing, lead scoring, account scoring, or sales-assist workflows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience working in a high-growth SaaS company with Sales, Marketing, Customer Success, and Finance stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Basic scripting experience in Python, JavaScript, or another language.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with Salesforce Flow, Apex, HubSpot Operations Hub, APIs, webhook-based automation, or reverse ETL tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What we bring to the table\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏥 100% employer-paid benefits + a Health Spending Account from day one\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🌎 Work from anywhere in the world for up to 4 weeks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💰 Stock option plan—own a piece of our success\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💲 RRSP Group Savings Plan to plan for your future\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏝 Generous vacation package to recharge and relax\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;📚 Personal development budget to fuel your growth\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🧖 One personal day + two volunteering days to give back\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🎂 Your Birthday off—celebrate on us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🍎 Five health days per year to stay at your best\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Compensation \u0026amp;amp; Work Details\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The base salary range for this role is $120,000 CAD - $150,000 CAD. Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re always happy to answer questions about compensation throughout the hiring process.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a net new position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week to promote collaboration\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ranked by the Globe \u0026amp;amp; Mail \u0026lt;/strong\u0026gt;as one of Canada’s fastest-growing companies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™\u0026lt;/strong\u0026gt; awards for revenue growth over the \u0026lt;strong\u0026gt;past four years\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ \u0026lt;/strong\u0026gt;as one of the fastest-growing companies in North America\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Raised $55 million Series A financing\u0026lt;/strong\u0026gt; in 2023\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Diversity is our strength\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;AI Disclosure:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.\u0026lt;/p\u0026gt;","departments":[{"id":4025606006,"name":"Revenue Operations","child_ids":[],"parent_id":null}],"offices":[{"id":4005312006,"name":"Toronto","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/contactmonkey/jobs/4677805006","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":4545854006,"location":{"name":"Toronto "},"metadata":null,"id":4677805006,"updated_at":"2026-05-22T14:42:56-04:00","requisition_id":"155","title":"Principal Software Engineer","company_name":"ContactMonkey","first_published":"2026-05-04T15:11:53-04:00","language":"en","application_deadline":null,"content":"\u0026lt;p\u0026gt;Hey there! We’re ContactMonkey 👋\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the job - Principal Software Engineer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;ContactMonkey\u0026#39;s platform already runs AI in production - AI-powered template editing, a standalone ConfidenceCheck service that evaluates outgoing emails for editorial quality and link safety, Braintrust-backed evaluations, and per-organization feature gating. The next wave is bigger: grounded assistants, retrieval over customer brand and campaign history, richer agentic flows inside the composer, and data products that make sending decisions smarter.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re forming a dedicated AI pod to own that trajectory. With the team you will be setting the technical direction for the pod, make the foundational infrastructure bets (vector store, evals, data warehouse, agent orchestration), and ship the first production systems yourself. AI is a major thrust, and the Principal Engineer will set technical direction across this work — making the foundational infrastructure bets. This is a lead position role in the sense that you own the shape of the thing - it is not a role where you stop writing code.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Your impact:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI platform direction:\u0026lt;/strong\u0026gt; Model selection and routing, prompt and context architecture, evaluation strategy, cost and latency budgets, safety and PII handling. Decide where we go deeper with frontier models, where we fine-tune smaller ones, and where classical ML beats an LLM.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Retrieval and grounding infrastructure\u0026lt;/strong\u0026gt;: You\u0026#39;ll pick it, design the ingestion path (brand kits, past campaigns, template library, per-org knowledge), own the chunking/embedding/refresh strategy, and set the quality bar via evals.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Agent and tool-use patterns:\u0026lt;/strong\u0026gt; Multi-turn tool-calling loops, deterministic fallbacks, observability, recoverable failure modes across Sidekiq and SQS, human-in-the-loop checkpoints where they matter.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Data engineering foundations\u0026lt;/strong\u0026gt;: You\u0026#39;ll decide whether we need a warehouse (BigQuery / Snowflake / DuckDB-on-S3/ RedShift), design the pipelines that feed both product analytics and model training/eval datasets, and make sure the lineage is clean enough that we trust what we ship. Build a foundation for the next level data analytics across the company.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cloud and deployment architecture: \u0026lt;/strong\u0026gt;We run on AWS (ECS, S3, SQS etc). You\u0026#39;ll make the calls on how AI services are deployed - when a new microservice like ConfidenceCheck is the right pattern vs. embedding in the Rails monolith, how we handle GPU/accelerated inference if we ever need it, how we isolate model spend per tenant.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What we expect from you technically:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You should be credible across all four of AI, Cloud, Data, and Fullstack - not a specialist in one with passing knowledge of the others.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Concretely:\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;AI / ML\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Built and operated LLM-backed features in production against real users.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Deep familiarity with at least one major provider SDK (Anthropic, OpenAI, AWS Bedrock) and comfort switching between them. Understand prompt caching, structured outputs, tool use, and the tradeoffs between agent loops and pipeline-style orchestration.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evals are a reflex, not an afterthought. You\u0026#39;ve run a real eval harness (Braintrust, promptfoo, in-house) against golden datasets and used it to block regressions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Working knowledge of retrieval systems: embeddings, hybrid search, reranking, and where each breaks. Opinions on pgvector vs. dedicated vector DBs and when either is wrong.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: fine-tuning or distillation experience, classical ML for ranking/classification, prompt-injection and jailbreak threat modelling.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Cloud\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;AWS fluency at the architecture level - VPCs, IAM boundaries, secrets management, queue-based decoupling, cost control.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Container-native deployment (ECS, EKS, or equivalent). IaC experience (Terraform or CDK) - even if we aren\u0026#39;t using it yet, you should expect to bring it in.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Have operated production systems under real load. You\u0026#39;ve been paged, and you\u0026#39;ve written the postmortem.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Data Engineering\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Can design a data pipeline end-to-end: ingestion, transformation, storage, serving. Batch and streaming. Have built this in at least one real organization.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfortable with SQL and non SQL at a level that lets you reason about query plans, not just write queries. You\u0026#39;ve tuned a slow query by looking at the plan, not by guessing.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Opinion on when a warehouse earns its keep vs. when read replicas are enough. We\u0026#39;re at that decision point.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Bonus: dbt, Airflow / Dagster / Prefect, CDC patterns, multi-tenant data partitioning at scale.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Fullstack\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Our backend is Ruby on Rails and our frontends is Vue.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Write real TypeScript. The AI-adjacent services are TS-first and that is likely to grow.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Understand API design past the happy path - versioning, auth modes (we run session auth for the main API and bearer tokens for integrations), rate limiting, idempotency.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What we bring to the table\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏥 100% employer-paid benefits + a Health Spending Account from day one\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🌎 Work from anywhere in the world for up to 4 weeks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💰 Stock option plan—own a piece of our success\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💲 RRSP Group Savings Plan to plan for your future\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏝 Generous vacation package to recharge and relax\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;📚 Personal development budget to fuel your growth\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🧖 One personal day + two volunteering days to give back\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🎂 Your Birthday off—celebrate on us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🍎 Five health days per year to stay at your best\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Compensation \u0026amp;amp; Work Details\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re always happy to answer questions about compensation throughout the hiring process.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a net new position based out of our downtown Toronto office, at King and Spadina. Our engineering team works primarily remote but we are looking for someone who is willing to come into the office occasionally on an as needed basis.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ranked by the Globe \u0026amp;amp; Mail \u0026lt;/strong\u0026gt;as one of Canada’s fastest-growing companies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™\u0026lt;/strong\u0026gt; awards for revenue growth over the \u0026lt;strong\u0026gt;past four years\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ \u0026lt;/strong\u0026gt;as one of the fastest-growing companies in North America\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Raised $55 million Series A financing\u0026lt;/strong\u0026gt; in 2023\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Diversity is our strength\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;AI Disclosure:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.\u0026lt;/p\u0026gt;","departments":[{"id":4009928006,"name":"Engineering ","child_ids":[],"parent_id":null}],"offices":[{"id":4005312006,"name":"Toronto","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/contactmonkey/jobs/4661903006","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":4537917006,"location":{"name":"Toronto "},"metadata":null,"id":4661903006,"updated_at":"2026-04-27T14:46:43-04:00","requisition_id":"153","title":"Senior AI Engineer","company_name":"ContactMonkey","first_published":"2026-03-10T14:55:04-04:00","language":"en","application_deadline":null,"content":"\u0026lt;p\u0026gt;Hey there! We’re ContactMonkey 👋\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About the job - AI Engineer\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Join the Engineering Team, where you’ll help shape and build our agentic future.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’ll work closely with our Product and Engineering Teams, and our Chief Product \u0026amp;amp; Technology Officer (CPTO), to turn vision into reality, partnering with a small, high-impact team to design, prototype, and ship AI-powered capabilities quickly. This role is hands-on and iterative, focused on building production-grade\u0026lt;strong\u0026gt; \u0026lt;/strong\u0026gt;agentic workflows that improve how internal communications are curated, designed, delivered, measured, and orchestrated.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Your impact\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Architectural Ownership:\u0026lt;/strong\u0026gt; Contribute to the technical vision for our AI layer, driving technology adoption and research initiatives from spike to task breakdown, with a focus on core AI infrastructure to ensure our systems are robust and scalable.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Agentic Design \u0026amp;amp; Orchestration:\u0026lt;/strong\u0026gt; Move beyond simple features to architect and implement robust agentic workflows, multi-agent systems, intelligent system behaviors, and orchestration patterns (e.g., dynamic routing, autonomous agents, feedback loops).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Strategic Execution \u0026amp;amp; Experimentation:\u0026lt;/strong\u0026gt; Operate with autonomy by building and executing against a 3-month strategic roadmap while refining work as you learn. Design and execute different approaches and experimentation frameworks to benchmark model value, measure success, and systematically iterate on prompts and model configurations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Production Ownership \u0026amp;amp; Reliability:\u0026lt;/strong\u0026gt; Own the reliability and scalability of AI subsystems in production, so our AI layer stays trustworthy as it grows. This includes designing and implementing comprehensive testing strategies that move beyond existing framework, focusing on systematic testing of LLM responses and failure modes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cross-Functional Partnership:\u0026lt;/strong\u0026gt; Collaborate closely with Product Management and the CPTO to translate business vision into concrete technical specifications and product-facing or internal workflow automation tools.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lead by Example\u0026lt;/strong\u0026gt;: Be active within your team and the company. Participate in meetings; volunteer to lead initiatives; escalate questions or issues when necessary. Act as a subject matter expert for complex subsystem troubleshooting, cross-org dependencies, and architectural reviews, including how to structure and maintain documentation (e.g., using agents, markdown, or external Knowledge Bases).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cultural Stewardship:\u0026lt;/strong\u0026gt; Be a full participant in helping the engineering culture evolve as we grow.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;About you\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You hold a Bachelor’s degree (or higher) in Computer Science, Statistics, Mathematics, or Engineering, or equivalent practical experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;7+ years of professional software engineering experience, including 2+ years building AI/ML or data-driven systems in production SaaS environments\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You possess deep technical proficiency in AI systems, including handling complex subsystem interactions and dependencies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You\u0026#39;ve moved LLM work past prototypes into production—thinking through eval frameworks, monitoring output quality, and iterating on prompts based on real-world performance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You understand how to structure LLM calls for reliability: using function calling to ground outputs, testing responses systematically, and designing for failure modes (hallucinations, latency, cost).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have working knowledge of multi-agent orchestration frameworks and RAG architectures, including vector stores.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You prioritize a \u0026quot;question first, then answer\u0026quot; approach, thinking critically about problems before committing to a code path.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You bring intellectual humility, empathy, and strong listening skills to the team; you lead by example.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You are able to work collaboratively and independently.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You are comfortable with agile development.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have excellent oral and written communication skills.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How you can stand out\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;You have designed and shipped autonomous workflows where LLMs reason across multiple steps, make decisions based on tool outputs, and adapt their behavior based on feedback.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have previous experience working within the email ecosystem or similar high-scale communication platforms.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You have a proven track record of rapid prototyping, iterating quickly on features, and leveraging data to pivot when necessary.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You act as a catalyst for new engineering principles and tools within your current organization, helping to raise the technical bar for your peers.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What we bring to the table\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏥 100% employer-paid benefits + a Health Spending Account from day one\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🌎 Work from anywhere in the world for up to 4 weeks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💰 Stock option plan—own a piece of our success\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💲 RRSP Group Savings Plan to plan for your future\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🏝 Generous vacation package to recharge and relax\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;📚 Personal development budget to fuel your growth\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🧖 One personal day + two volunteering days to give back\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🎂 Your Birthday off—celebrate on us!\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;🍎 Five health days per year to stay at your best\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Compensation \u0026amp;amp; Work Details\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’re always happy to answer questions about compensation throughout the hiring process.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a net new position for our AI Engineering Team based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week or as needed to promote collaboration\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ranked by the Globe \u0026amp;amp; Mail \u0026lt;/strong\u0026gt;as one of Canada’s fastest-growing companies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™\u0026lt;/strong\u0026gt; awards for revenue growth over the \u0026lt;strong\u0026gt;past four years\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ \u0026lt;/strong\u0026gt;as one of the fastest-growing companies in North America\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Raised $55 million Series A financing\u0026lt;/strong\u0026gt; in 2023\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Diversity is our strength\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;AI Disclosure:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.\u0026lt;/p\u0026gt;","departments":[{"id":4009928006,"name":"Engineering ","child_ids":[],"parent_id":null}],"offices":[{"id":4005312006,"name":"Toronto","location":"Toronto, Ontario, Canada","child_ids":[],"parent_id":null}]}],"meta":{"total":4}}