{"jobs":[{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6002626004","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":5157588004,"location":{"name":"Remote"},"metadata":null,"id":6002626004,"updated_at":"2026-06-02T19:00:09-04:00","requisition_id":"585","title":"Compliance \u0026 Legal Operations Manager","company_name":"HopSkipDrive","first_published":"2026-06-02T19:00:09-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our lean, high-trust Legal \u0026amp;amp; Compliance team is foundational to HopSkipDrive\u0026#39;s expansion, directly managing the multi-state regulatory infrastructure and operational systems that power our growth. We support the business and build scalable programs through the following primary responsibilities:\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Regulatory Research \u0026amp;amp; Market Expansion:\u0026lt;/strong\u0026gt; Lead compliance analysis for new and existing state markets and develop state-specific documentation\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Client-Facing Compliance Support:\u0026lt;/strong\u0026gt; Act as the primary point of contact for school districts on compliance and regulatory questions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ironclad System Administration:\u0026lt;/strong\u0026gt; Serve as the platform owner for Ironclad, configuring workflows, maintaining integrations with Salesforce/Airbase, and driving internal process documentation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Contract Data \u0026amp;amp; Repository Management:\u0026lt;/strong\u0026gt; Own contract metadata extraction, define data models, and track terms in ClickUp and master tables to ensure renewal readiness.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Legal Operations and Financial Oversight:\u0026lt;/strong\u0026gt; Lead outside counsel management by reviewing vendor invoices and establishing billing discipline to optimize external legal spend.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Risk Review \u0026amp;amp; Policy Development:\u0026lt;/strong\u0026gt; Partner on data privacy, SOC 2 maintenance, and vendor risk reviews while drafting internal legal guidelines and compliance SOPs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI Tool Administration:\u0026lt;/strong\u0026gt; Manage legal-specific AI tool licensing, seats, onboarding, and new-feature rollouts as the team\u0026#39;s primary technical resource.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI-Assisted Workflow Automation:\u0026lt;/strong\u0026gt; Identify workflow leverage areas to build and iterate on compliance dashboards, intake chatbots, and automated tech stack solutions.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a collaborative, tech-forward professional who thrives at the intersection of regulatory complexity and emerging technology, ready to build systems that scale. You bring the following essential experiences and mindsets to our team:\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Regulated Industry Experience:\u0026lt;/strong\u0026gt; 4–7 years of dedicated experience in compliance, legal operations, or a closely related highly regulated field.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Ironclad Mastery:\u0026lt;/strong\u0026gt; Proven hands-on experience administering and configuring workflows within the Ironclad contract lifecycle management platform.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Technical Adaptability \u0026amp;amp; AI Agility:\u0026lt;/strong\u0026gt; Demonstrated track record of independently adopting, administering, and leveraging generative AI tools to accelerate professional workflows.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Regulatory Research Skills:\u0026lt;/strong\u0026gt; Strong capability to analyze complex, state-level regulatory frameworks and synthesize them into clear, actionable resources.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Multi-Project Management:\u0026lt;/strong\u0026gt; Proven ability to manage concurrent workstreams across different states, issue types, and cross-functional stakeholders simultaneously.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Process \u0026amp;amp; System Building:\u0026lt;/strong\u0026gt; A foundational background in establishing, scaling, and continuously improving operational legal systems and organizational frameworks.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;External Partner Communication:\u0026lt;/strong\u0026gt; Experience drafting high-stakes professional documentation and interfacing directly with external clients or district partners.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;br\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $110,000.00 - $115,000.00. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;* This is a fully remote role. Candidates must reside in and perform work from one of the following states: \u0026lt;strong\u0026gt;AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or\u0026amp;nbsp; WI\u0026lt;/strong\u0026gt;. We are not currently considering candidates who will perform work from any other state.\u0026lt;/p\u0026gt;","departments":[{"id":4017357004,"name":"Legal","child_ids":[],"parent_id":4103598004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5848097004","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":5073214004,"location":{"name":"Remote USA "},"metadata":null,"id":5848097004,"updated_at":"2026-06-04T12:10:13-04:00","requisition_id":"578","title":"Data Analyst - Revenue Ops","company_name":"HopSkipDrive","first_published":"2026-04-22T19:21:11-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our Data Science and Analytics team is a fast-moving, AI-forward group, that utilizes a modern data stack including SQL, dbt, and Snowflake to deliver accurate data across the company. This analyst role will provide a direct, embedded partnership to the Revenue Operations (RevOps) group. You will:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Support quota and attainment reporting, giving RevOps leadership real-time visibility into performance versus targets.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Analyze funnel conversion, win/loss rates, and revenue trends to surface growth opportunities and churn risks for RevOps to act on.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Contribute to dynamic, scenario-contingent models for revenue forecasting and pricing analysis using Excel, Google Sheets, and/or modern BI tools.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Sales leadership on forecasting by providing growth metrics and forward-looking projections to inform planning decisions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Maintain and improve Snowflake and dbt data models to ensure accurate, consistent reporting in the source data.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Version-control all data products in GitHub and build automations to eliminate recurring manual tasks.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Translate complex data findings into clear, decision-driving language for Sales and RevOps stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Develop self-serve reporting tools that allow business leaders to answer day-to-day questions independently.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;:\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a proactive, technically-grounded analyst who moves fast and understands the intricacies of the sales motion and revenue operations. You are inherently curious love to think critically about the details and the big picture.\u0026amp;nbsp; You are an expert at interpreting business requests and translating them into rigorous, reproducible analysis while utilizing AI tools to enhance your workflow. You excel at building strong cross-functional relationships to drive alignment on key business objectives. You have excellent communication skills and can translate findings for both technical and non-technical audiences. \u0026lt;br\u0026gt;\u0026lt;br\u0026gt;5+ years of experience in a data-intensive analyst role at a technology company, specifically within Sales or Revenue Operations.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Advanced, production-grade SQL skills with the ability to build reliable models and debug complex data issues independently.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven expertise building sophisticated, dynamic models in Excel or Google Sheets for scenario planning and revenue forecasting.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Direct experience working with dbt for data modeling and transformation within a cloud data warehouse like Snowflake.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Technical proficiency with Salesforce CRM data models, reporting structures, and data hygiene practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience using modern BI tools (such as Tableau, Looker, or Omni) to build reports and self-serve analytics.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated ability to use GitHub for version control, documentation, and maintaining reproducible data pipelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience integrating AI systems like Claude into your analytical workflow to increase speed and accuracy.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $95,000 - $110,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;","departments":[{"id":4067792004,"name":"Data","child_ids":[],"parent_id":4103599004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5850151004","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":5074310004,"location":{"name":"Remote USA"},"metadata":null,"id":5850151004,"updated_at":"2026-05-29T13:19:03-04:00","requisition_id":"583","title":"Government Relations Manager","company_name":"HopSkipDrive","first_published":"2026-04-16T12:37:22-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p data-path-to-node=\u0026quot;4\u0026quot;\u0026gt;\u0026lt;strong data-path-to-node=\u0026quot;4\u0026quot; data-index-in-node=\u0026quot;0\u0026quot;\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;5\u0026quot;\u0026gt;We are a team of advocacy and legislative professionals working to drive change through rulemaking, community organizing, and coalition building to support our policy priorities. Our small but impactful team is composed of creative problem-solvers dedicated to advancing transportation equity through strategic government relations.\u0026lt;/p\u0026gt;\n\u0026lt;ul data-path-to-node=\u0026quot;6\u0026quot;\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,0,0\u0026quot;\u0026gt;Monitor, analyze, and track legislative and regulatory activity across assigned markets to identify business risks and opportunities.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,1,0\u0026quot;\u0026gt;Build and maintain working relationships with policymakers, agency staff, legislative aides, and third-party advocates.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,2,0\u0026quot;\u0026gt;Draft high-impact position papers, testimony, comment letters, and internal policy memos.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,3,0\u0026quot;\u0026gt;Support the coordination of external lobbyists and advocacy consultants in assigned jurisdictions.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,4,0\u0026quot;\u0026gt;Partner with cross-functional teams, including Legal and Operations, to translate policy developments into actionable business guidance.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,5,0\u0026quot;\u0026gt;Represent HopSkipDrive in stakeholder meetings, coalition convenings, and public forums.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,6,0\u0026quot;\u0026gt;Contribute to internal reporting on legislative status, hearing calendars, and advocacy progress.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;6,7,0\u0026quot;\u0026gt;Utilize AI tools to support research, drafting, and workflow efficiency consistent with team standards.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;7\u0026quot;\u0026gt;\u0026lt;strong data-path-to-node=\u0026quot;7\u0026quot; data-index-in-node=\u0026quot;0\u0026quot;\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;8\u0026quot;\u0026gt;You are a highly organized, detail-oriented strategist with a proven track record in developing and overseeing results-driven policy campaigns. You are a skilled communicator who can navigate complex regulatory language and serve as a key advisor on all matters related to government affairs.\u0026lt;/p\u0026gt;\n\u0026lt;ul data-path-to-node=\u0026quot;9\u0026quot;\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,0,0\u0026quot;\u0026gt;At least 5-6 years of combined experience in government relations, regulatory agencies, or public policy roles.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,1,0\u0026quot;\u0026gt;Proven ability to research and analyze statutes and regulations with high attention to detail.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,2,0\u0026quot;\u0026gt;Demonstrated experience with the legislative process and managing relationships with external lobbyists.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,3,0\u0026quot;\u0026gt;Strong ability to translate complex policy impacts into clear guidance for business stakeholders.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,4,0\u0026quot;\u0026gt;Exceptional communication skills with experience serving as a public face to policymakers and governmental contacts.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,5,0\u0026quot;\u0026gt;Proven track record of building relationships with diverse stakeholders to further organizational missions.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,6,0\u0026quot;\u0026gt;Highly organized with the ability to manage and advance several policy initiatives simultaneously.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;9,7,0\u0026quot;\u0026gt;Strategic mindset with the ability to identify policy-related opportunities in rapidly shifting markets.\u0026lt;/p\u0026gt;\n\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;10\u0026quot;\u0026gt;\u0026lt;strong data-path-to-node=\u0026quot;10\u0026quot; data-index-in-node=\u0026quot;0\u0026quot;\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p id=\u0026quot;p-rc_747ddd49b8420ba3-21\u0026quot; data-path-to-node=\u0026quot;11\u0026quot;\u0026gt;We want you to be \u0026lt;span class=\u0026quot;citation-492 citation-493 citation-end-493\u0026quot;\u0026gt;an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positione\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;citation-492 citation-end-492\u0026quot;\u0026gt;d, VC-backed company in a hugely attractive space with significant\u0026lt;/span\u0026gt; upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $120,000 - $135,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation \u0026lt;span class=\u0026quot;citation-491\u0026quot;\u0026gt;for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, \u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;citation-490 citation-491 citation-end-491\u0026quot;\u0026gt;and specific work location. The total compensation package for this role also includes equity stock option\u0026lt;/span\u0026gt;\u0026lt;span class=\u0026quot;citation-490 citation-end-490\u0026quot;\u0026gt;s.\u0026lt;/span\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p id=\u0026quot;p-rc_747ddd49b8420ba3-22\u0026quot; data-path-to-node=\u0026quot;12\u0026quot;\u0026gt;\u0026lt;span class=\u0026quot;citation-489 citation-end-489\u0026quot;\u0026gt;HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employ\u0026lt;/span\u0026gt;ment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p data-path-to-node=\u0026quot;13,0,0\u0026quot;\u0026gt;*This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI*\u0026lt;/p\u0026gt;","departments":[{"id":4084654004,"name":"Government Affairs \u0026 Public Policy","child_ids":[],"parent_id":4103598004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5980234004","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":5146407004,"location":{"name":"Remote USA"},"metadata":null,"id":5980234004,"updated_at":"2026-05-28T18:36:10-04:00","requisition_id":null,"title":"Marketplace \u0026 Launch Operations Manager ","company_name":"HopSkipDrive","first_published":"2026-04-30T16:01:21-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;The New Markets team is a fast-moving, high-impact group focused on launching and scaling operations in new regions. We are looking for an analytical, adaptable, and proactive operator to join our team and own the end-to-end success of our marketplace performance.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Own near-term supply and demand forecasts for launch markets by designing and maintaining predictive models aligned to company directives.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Operate and optimize marketplace configurations, including zip code mapping and cluster assignments, to maximize supply-demand matching efficiency.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Design, build, and ship targeted productivity promotions to address fill rate gaps, manage market spend, and drive operational efficiency.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Evaluate market health by monitoring net revenue and contribution margin, recommending cross-functional remediation for struggling markets.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Monitor performance trends proactively, identifying root causes of off-track metrics and bringing forward data-backed recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own end-to-end project workstreams by defining scope, identifying owners, tracking progress, and ensuring cross-functional execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Leverage AI-assisted workflows to accelerate research, monitor territory performance, and pressure-test strategic recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a high-agency operator who thrives in ambiguous environments and possesses a relentless drive to solve complex operational challenges. You have a proven track record of managing stakeholders, utilizing data to influence outcomes, and building scalable processes from the ground up.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;3+ years of experience driving superior results in analytical, cross-functional, or operations roles, ideally in marketplace, logistics, or high-growth environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excel/Google Sheets power user capable of building complex, elegant models with advanced formulas and dashboards that work for non-technical stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated ability to make nuanced business decisions based on imperfect information while remaining accountable for the outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to lead projects involving stakeholders who do not report to you, aligning teams and resolving friction to drive closure.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong communication skills with the ability to translate complexity for different functions and levels without losing precision.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High agency in identifying necessary actions and executing them independently in a fast-moving environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience independently pulling and structuring data, with comfort using SQL or other data querying tools.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Working knowledge of Tableau; expected to grow in report-building and contribute to team dashboards\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated comfort using AI tools (such as Claude, ChatGPT, Perplexity, or equivalent) as an integral part of your actual daily workflow.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You’ll flex across the full lifecycle of a launch — from infrastructure setup to cross-functional coordination to performance monitoring — doing whatever it takes to get a city operational and on a path to contribution margin positive.\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;This is not a role for people who wait for direction. It’s for operators who identify gaps, build the tools to close them, and hold themselves accountable to outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;h3\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/h3\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 95,000 - 110,000.\u0026amp;nbsp; This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;**This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**\u0026amp;nbsp; Prioritizing candidates in Eastern and Southeast states based on business needs.\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4074432004,"name":"Growth Initiatives","child_ids":[],"parent_id":4103596004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6014607004","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":5162473004,"location":{"name":"Remote USA "},"metadata":null,"id":6014607004,"updated_at":"2026-06-04T23:44:31-04:00","requisition_id":"588","title":"Metro Service Manager","company_name":"HopSkipDrive","first_published":"2026-06-04T23:44:18-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role will provide exceptional, proactive support for our clients throughout the operational lifecycle. This position bridges the gap between Implementation, Customer Success, and ongoing Operations to streamline service delivery and ensure a premium client experience.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The Metro Service Manager will take ownership of ongoing client operations and issue resolution. This new role will work closely with cross-functional teams to proactively address client needs, improve service quality, and optimize ride experiences. We are looking for creative problem-solvers who, like us, believe that challenges require innovative approaches, unique perspectives, and new ways of thinking.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Serve as the primary point of contact for assigned clients, ensuring needs are addressed and solutions delivered with urgency and professionalism.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Respond to and resolve complex client inquiries, leveraging internal resources and collaboration to provide swift resolutions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead and manage the implementation of new business from contract signed through launch, ensuring a successful implementation process and maintaining communication with clients throughout the implementation\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Act as a trusted advisor by continuously learning about HopSkipDrive\u0026#39;s evolving products and services to best support clients.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Gather and analyze feedback on ride experiences to identify improvement opportunities and implement service enhancements.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with cross-functional teams to address systemic issues affecting client satisfaction and advocate for impactful changes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Customer Support Specialists to resolve real-time ride and account issues while delivering weekly optimization reports.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct virtual and in-person client meetings to strengthen relationships, align on goals, and ensure adoption of best practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive the strategic planning and execution of business reviews to align ongoing service strategies with client objectives.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’re a proactive and strategic customer success professional who excels at building strong client relationships, solving complex challenges, and driving measurable results. You thrive in fast-paced environments and are passionate about enhancing client experiences through data-driven insights and collaboration.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of experience in Customer Success, Account Management, or Implementation roles, preferably in a high-pressure or start-up environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Willingness to travel (10%-20%) to strengthen client relationships and support service strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to manage client relationships, resolve issues swiftly, and deliver exceptional customer service.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong communication skills, both written and verbal, with the ability to present insights and solutions effectively in meetings and reports.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Expertise in analyzing data, identifying trends, and implementing actionable solutions to improve client outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating across teams to address root causes of recurring challenges and enhance service delivery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with CRM tools such as Salesforce or Kustomer, and advanced Excel skills are preferred.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A proactive, problem-solving mindset with the initiative to drive continuous improvement and innovation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You are tech-forward and committed to operational excellence. You actively leverage AI tools (such as Gemini) to streamline workflows, summarize complex client issues, refine communication, and derive insights from data sets, and you are eager to apply this expertise to enhance client outcomes\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The base salary range for this role is $80,000 - $90,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;*NOTE* This role will be remote but candidates must be able to travel occasionally regionally (10-20%).\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;","departments":[{"id":4017353004,"name":"Customer Success","child_ids":[],"parent_id":4103596004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5980236004","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":5146408004,"location":{"name":"Remote Arizona"},"metadata":null,"id":5980236004,"updated_at":"2026-05-04T16:26:06-04:00","requisition_id":null,"title":"Metro Service Manager","company_name":"HopSkipDrive","first_published":"2026-04-29T02:59:21-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who we are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This role will provide exceptional, proactive support for our clients throughout the operational lifecycle. This position bridges the gap between Implementation, Customer Success, and ongoing Operations to streamline service delivery and ensure a premium client experience.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The Metro Service Manager will take ownership of ongoing client operations and issue resolution. This new role will work closely with cross-functional teams to proactively address client needs, improve service quality, and optimize ride experiences. We are looking for creative problem-solvers who, like us, believe that challenges require innovative approaches, unique perspectives, and new ways of thinking.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Serve as the primary point of contact for assigned clients, ensuring needs are addressed and solutions delivered with urgency and professionalism.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Respond to and resolve complex client inquiries, leveraging internal resources and collaboration to provide swift resolutions.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Lead and manage the implementation of new business from contract signed through launch, ensuring a successful implementation process and maintaining communication with clients throughout the implementation\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Act as a trusted advisor by continuously learning about HopSkipDrive\u0026#39;s evolving products and services to best support clients.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Gather and analyze feedback on ride experiences to identify improvement opportunities and implement service enhancements.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaborate with cross-functional teams to address systemic issues affecting client satisfaction and advocate for impactful changes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner with Customer Support Specialists to resolve real-time ride and account issues while delivering weekly optimization reports.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Conduct virtual and in-person client meetings to strengthen relationships, align on goals, and ensure adoption of best practices.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Drive the strategic planning and execution of business reviews to align ongoing service strategies with client objectives.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You’re a proactive and strategic customer success professional who excels at building strong client relationships, solving complex challenges, and driving measurable results. You thrive in fast-paced environments and are passionate about enhancing client experiences through data-driven insights and collaboration.\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of experience in Customer Success, Account Management, or Implementation roles, preferably in a high-pressure or start-up environment.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Willingness to travel (10%-20%) to strengthen client relationships and support service strategies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ability to manage client relationships, resolve issues swiftly, and deliver exceptional customer service.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong communication skills, both written and verbal, with the ability to present insights and solutions effectively in meetings and reports.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Expertise in analyzing data, identifying trends, and implementing actionable solutions to improve client outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience collaborating across teams to address root causes of recurring challenges and enhance service delivery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency with CRM tools such as Salesforce or Kustomer, and advanced Excel skills are preferred.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;A proactive, problem-solving mindset with the initiative to drive continuous improvement and innovation.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;You are tech-forward and committed to operational excellence. You actively leverage AI tools (such as Gemini) to streamline workflows, summarize complex client issues, refine communication, and derive insights from data sets, and you are eager to apply this expertise to enhance client outcomes\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The base salary range for this role is $80,000 - $90,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;*NOTE* This role will be remote but candidates must be based in the Arizona metro. There will be occasional (10-20%) travel required as well.\u0026amp;nbsp;\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;","departments":[{"id":4017353004,"name":"Customer Success","child_ids":[],"parent_id":4103596004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6002628004","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":5157589004,"location":{"name":"Remote"},"metadata":null,"id":6002628004,"updated_at":"2026-06-02T18:59:48-04:00","requisition_id":"584","title":"Paralegal","company_name":"HopSkipDrive","first_published":"2026-06-02T18:59:48-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our lean Legal \u0026amp;amp; Compliance team takes pride in operating as a high-trust, directly embedded partner to the business. We are a broad-scope, fast-moving team dedicated to building scalable tracking systems, protecting the company, and accelerating operations through the deliberate use of AI-forward legal tools.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We do, and you will, support the business through the following responsibilities:\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Contract Queue Management:\u0026lt;/strong\u0026gt; Manage the contract review queue end-to-end, including first drafts, redline cycles, counterparty coordination, and signature tracking.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Agreement Drafting:\u0026lt;/strong\u0026gt; Draft and redline standard agreements, including NDAs, vendor contracts, SOW amendments, and service contracts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Repository \u0026amp;amp; Template Ownership:\u0026lt;/strong\u0026gt; Maintain the contract repository within the CLM system and ensure the template library remains current and retrievable.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lifecycle Tracking:\u0026lt;/strong\u0026gt; Proactively flag upcoming contract renewals, key dates, non-standard terms, and counterparty obligations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Intake \u0026amp;amp; Matter Triage:\u0026lt;/strong\u0026gt; Triage incoming legal requests, route matters to the appropriate team members, and monitor compliance with contractual SLAs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Litigation Support \u0026amp;amp; Holds:\u0026lt;/strong\u0026gt; Coordinate document preservation notices, oversee litigation hold requests, track custodian compliance, and support discovery.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Legal Proceeding Operations:\u0026lt;/strong\u0026gt; Manage court filings, deadline calendaring, and procedural compliance for garnishments and external information requests.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI \u0026amp;amp; Workflow Optimization:\u0026lt;/strong\u0026gt; Utilize specialized generative AI tools to accelerate legal research, draft summaries, and continuously optimize team workflow efficiency.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a sharp, process-oriented legal professional who thrives in a growth-stage environment and takes genuine pride in operational excellence. You are an independent self-starter who can navigate ambiguity, build workflows from scratch, and ensure zero critical legal deadlines are missed.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You bring the following essential experiences and mindsets to our team:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Professional Paralegal Experience:\u0026lt;/strong\u0026gt; 4–6 years of dedicated paralegal experience within a law firm or fast-growing company managing significant volume.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Commercial Contracting Skills:\u0026lt;/strong\u0026gt; Proven ability to draft, review, and redline contracts (NDAs, vendor agreements, SOWs) with high attention to detail.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Systems Expertise:\u0026lt;/strong\u0026gt; Hands-on experience navigating and managing legal operations within Ironclad or an equivalent modern CLM system.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Matter Tracking Proficiency:\u0026lt;/strong\u0026gt; Demonstrated success managing legal intake systems and balancing high-volume workstreams with competing deadlines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Litigation \u0026amp;amp; Discovery Competency:\u0026lt;/strong\u0026gt; Experience executing litigation holds, managing discovery coordination, and overseeing court filing timelines.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Regulated Industry Exposure:\u0026lt;/strong\u0026gt; Background working within a highly regulated environment, such as transportation, education, healthcare, or similar.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Technical \u0026amp;amp; AI Adaptability:\u0026lt;/strong\u0026gt; A tech-forward mindset with an active interest in experimenting with AI drafting assistance and research automation tools.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;br\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $80,000.00\u0026amp;nbsp; - $95,000.00. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;* This is a fully remote role. Candidates must reside in and perform work from one of the following states: \u0026lt;strong\u0026gt;AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or\u0026amp;nbsp; WI\u0026lt;/strong\u0026gt;. We are not currently considering candidates who will perform work from any other state.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;br\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/p\u0026gt;","departments":[{"id":4017357004,"name":"Legal","child_ids":[],"parent_id":4103598004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6009635004","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":5160429004,"location":{"name":"Remote USA "},"metadata":null,"id":6009635004,"updated_at":"2026-06-03T21:32:00-04:00","requisition_id":"587","title":"Regional Account Manager","company_name":"HopSkipDrive","first_published":"2026-06-03T21:32:00-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility — while making a meaningful difference for those who need it most.\u0026amp;nbsp;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;The Role\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management, the RAM sets and executes account strategy and provides recommendations to senior staff for required resources, collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires strong client communication skills, demonstrated commercial acumen, high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;In-Person Client Engagement: \u0026lt;/strong\u0026gt;Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Spearhead Enterprise Growth:\u0026lt;/strong\u0026gt; Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Manage Client Accounts\u0026lt;/strong\u0026gt;: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Seek Net-New Opportunities: \u0026lt;/strong\u0026gt;Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Communicate Tailored Value: \u0026lt;/strong\u0026gt;Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Partner Cross-Functionally: \u0026lt;/strong\u0026gt;Align Sales, Operations, Product, Finance, Trust \u0026amp;amp; Safety and Support around client priorities and optimize our offerings to their needs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lead Pricing Discussions:\u0026amp;nbsp;\u0026lt;/strong\u0026gt;Lead renewals and expansions, including structured negotiations and closing motions\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI Enabled Operational Excellence: \u0026lt;/strong\u0026gt;Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications.\u0026amp;nbsp;Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Required\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ownership of retention and expansion revenue.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong executive communication and presentation skills.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success managing complex, multi-stakeholder accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advanced CRM discipline and data fluency (Salesforce or equivalent).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience leading cross-functional account execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in ambiguity with accountability for outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High operational rigor and the ability to leverage AI into daily workflows\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience in education, government, or regulated markets.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Challenger or similar insight-led sales methodologies.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background in transportation, logistics, or marketplace platforms.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $85,000-90,000 base with an OTE of $130,000 - $140,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal-opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;NOTE* The role will require 2-3 days on-site client visits every week regionally.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4017328004,"name":"Sales","child_ids":[],"parent_id":4103597004}],"offices":[{"id":4008745004,"name":"LA HQ","location":"Los Angeles, California, United States","child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6002560004","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":5157553004,"location":{"name":"Remote USA"},"metadata":null,"id":6002560004,"updated_at":"2026-06-03T15:40:34-04:00","requisition_id":"582","title":"Sales Development Representative","company_name":"HopSkipDrive","first_published":"2026-05-29T22:15:04-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our team of Sales Development Representatives create the first stage relationships with prospects at some of the largest school districts in the country. Your goal is to educate prospects on HopSkipDrive’s service and schedule meetings for them to speak with our Account Executives. Our Sales Development Team is the engine that drives HopSkipDrive’s growth. Here is a short list of what you will be doing:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Work in conjunction with sales team to research and evaluate prospective leads\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Establish a rapport with potential prospects\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Use a consultative sales approach during outreach to accurately assess the needs of prospective clients\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Cold call and email identified leads and determine if there is a potential need for HSD’s services\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Utilize Salesforce CRM to manage sales funnel and determine outreach strategies\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Meet or exceed SDR quotas (includes email and phone calls)\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Qualify leads that express interest in HSD’s service and assign them to an Account Executive, creating Sales Qualified Lead.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Meet or exceed assigned monthly and quarterly goals set forth by management.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a self-starter who is looking for a challenging and rewarding experience. The role of an SDR requires curiosity, great communication and persistence. We are building a team of creative problem-solvers from many different backgrounds who are excited to develop their skills. With the following skills, you’ll make a tangible and immediate impact:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Excellent written and verbal communication skills\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Honesty, empathy and curiosity for finding solutions for our prospective customers\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience handling objections\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Collaboration focused problem solving\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong desire for professional and personal growth\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience with CRM (Salesforce) platform preferred\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience in a sales or in the education space a plus\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong time management skills, creative problem solver, and self-sufficient worker\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proficiency in Google Suite and Microsoft Office\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $55,000 base + up to $20k OTE. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;* This role will be fully remote in one of the following states \u0026lt;strong\u0026gt;AZ, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI\u0026lt;/strong\u0026gt;**\u0026lt;/p\u0026gt;","departments":[{"id":4017328004,"name":"Sales","child_ids":[],"parent_id":4103597004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5989620004","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":5151237004,"location":{"name":"Remote USA"},"metadata":null,"id":5989620004,"updated_at":"2026-06-02T19:06:50-04:00","requisition_id":"579","title":"Senior Product Manager, Ops \u0026 Customer Experience","company_name":"HopSkipDrive","first_published":"2026-05-26T14:44:42-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;strong\u0026gt;\u0026lt;br\u0026gt;\u0026lt;br\u0026gt;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Our \u0026lt;strong\u0026gt;Support and Operational Productivity team\u0026lt;/strong\u0026gt; sits at the intersection of customer experience, operational excellence, and business growth. We\u0026#39;re a high-impact, collaborative group of product managers, engineers, designers, and operations specialists who build the systems and experiences that keep HopSkipDrive running — for our customers and for the teams that serve them.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our support world is uniquely complex.\u0026lt;/strong\u0026gt; We serve schools and parents coordinating their children’s transportation, school administrators managing district-wide logistics, drivers navigating complex pickup instructions and multi-stop coordination, and the operations team orchestrating it all. Every interaction involves multiple stakeholders, tight safety requirements, and real-time coordination.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our work spans the full operational landscape of HopSkipDrive\u0026lt;/strong\u0026gt; — from the customer-facing experiences that keep riders, CareDrivers, caregivers, and school partners informed and supported, to the internal platforms that power how our teams operate across support, sales, revenue operations, and safety. We think deeply about the people on both sides of every interaction: the customer navigating a problem, and the team member solving it. That dual lens — user experience and operational excellence, together — is what makes this work uniquely challenging and uniquely impactful.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We move fast, think big, and measure success by how much more effective we make our teams and how much better we serve our customers.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a seasoned, versatile \u0026lt;strong\u0026gt;Senior Product Manager\u0026lt;/strong\u0026gt; who leads with curiosity and conviction. You don\u0026#39;t just build features — you develop a deep understanding of your customers, your business, and your stakeholders, and use that understanding to make smart bets and drive real outcomes. You\u0026#39;re as comfortable in a strategic planning session as you are in a sprint review, and you have a track record of bringing people together around a shared vision.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Minimum of 8 years of experience\u0026lt;/strong\u0026gt; in product management, ideally spanning customer-facing platforms, operational tooling, or internal systems in complex, multi-stakeholder environments where reliability and user experience are non-negotiable.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Strong Customer Instincts: \u0026lt;/strong\u0026gt;a proven ability to build genuine, nuanced understanding of users through research and data, and to translate those insights into product decisions that matter\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Strategic Vision \u0026amp;amp; Execution\u0026lt;/strong\u0026gt;: You think in systems and over horizons. Skilled at defining multi-year product strategies, cutting through ambiguity to set clear direction, and driving execution from ideation through growth. You can zoom out to shape a roadmap and zoom in to unblock a team — and you know when to do each.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Cross-Functional Collaboration:\u0026lt;/strong\u0026gt; A proven partner to teams across the organization. You navigate competing priorities, broker alignment, and build the kind of collaborative relationships that make hard things possible. You understand that great product work happens at the intersection of functions, not in silos.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Platform \u0026amp;amp; Systems Thinking:\u0026lt;/strong\u0026gt; Comfortable building internal platforms, CRM solutions, and operational tooling that scales business processes and enables cross-functional teams. You think holistically about how systems interact and how tooling choices shape team performance and customer experience.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Data-Driven Decision Making: \u0026lt;/strong\u0026gt;Highly analytical. You leverage data, customer research, and operational metrics to inform product decisions, evaluate tradeoffs, and measure impact — and you foster that same orientation in the teams and stakeholders around you.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;Preferred experience that will set you up for success from day one:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Hands-on experience with customer support or helpdesk platforms such as Zendesk, Salesforce Service Cloud, or Intercom. Understanding how agents work, not just how the tools are configured\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with CRM systems and how they connect customer data, workflows, and team operations at scale\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building with or alongside generative AI tools, whether LLM-powered features, AI agents, or conversational experiences, with a practical understanding of where they work well and where they don\u0026#39;t\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience building internal tools or operational platforms that meaningfully changed how a team works\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background in industries where safety, trust, or care are central to the product — transportation, logistics, healthcare, childcare, or similar\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $160,000 - $180,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;* This is a fully remote role. Candidates must reside in and perform work from one of the following states: \u0026lt;strong\u0026gt;AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or\u0026amp;nbsp; WI\u0026lt;/strong\u0026gt;. We are not currently considering candidates who will perform work from any other state.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4017351004,"name":"Product","child_ids":[],"parent_id":4103599004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/5734603004","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":5018543004,"location":{"name":"Remote USA MN, WI, MI, PA, VA, MD, DC"},"metadata":null,"id":5734603004,"updated_at":"2026-05-28T18:37:37-04:00","requisition_id":"558","title":"Sr. Regional Account Manager ","company_name":"HopSkipDrive","first_published":"2025-12-11T02:41:21-05:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact.\u0026amp;nbsp; Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what\u0026#39;s possible in mobility-while making a meaningful difference for those who need it most.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;In-Person Client Engagement: \u0026lt;/strong\u0026gt;Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Spearhead Enterprise Growth:\u0026lt;/strong\u0026gt; Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Manage Client Accounts\u0026lt;/strong\u0026gt;: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Seek Net-New Opportunities: \u0026lt;/strong\u0026gt;Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Communicate Tailored Value: \u0026lt;/strong\u0026gt;Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Partner Cross-Functionally: \u0026lt;/strong\u0026gt;Align Sales, Operations, Product, Finance, Trust \u0026amp;amp; Safety and Support around client priorities and optimize our offerings to their needs\u0026lt;strong\u0026gt;.\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lead Pricing Discussions: \u0026lt;/strong\u0026gt;Lead renewals and expansions, including structured negotiations and closing motions\u0026lt;strong\u0026gt;.\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI Enabled Operational Excellence: \u0026lt;/strong\u0026gt;Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications.\u0026amp;nbsp;Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Required\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;8+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ownership of retention and expansion revenue.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong executive communication and presentation skills.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success managing complex, multi-stakeholder accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advanced CRM discipline and data fluency (Salesforce or equivalent).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience leading cross-functional account execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in ambiguity with accountability for outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience in education, government, or regulated markets highly preferred\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Challenger or similar insight-led sales methodologies highly preferred\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background in transportation, logistics, or marketplace platforms highly preferred\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High operational rigor and the ability to leverage AI into daily workflows\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $90,000-100,000 base with an OTE of $150,000 - $170,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal-opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;NOTE* This role will be based in MN, WI, MI, PA, VA, MD, DC. There will be travel required.\u0026amp;nbsp; The role will require 2-3 days on-site client visits every week.\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4017328004,"name":"Sales","child_ids":[],"parent_id":4103597004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6014647004","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":5162498004,"location":{"name":"Remote USA"},"metadata":null,"id":6014647004,"updated_at":"2026-06-04T23:42:49-04:00","requisition_id":"590","title":"Sr. Regional Account Manager ","company_name":"HopSkipDrive","first_published":"2026-06-04T23:42:49-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact.\u0026amp;nbsp; Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what\u0026#39;s possible in mobility-while making a meaningful difference for those who need it most.\u0026amp;nbsp;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;In-Person Client Engagement: \u0026lt;/strong\u0026gt;Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Spearhead Enterprise Growth:\u0026lt;/strong\u0026gt; Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Manage Client Accounts\u0026lt;/strong\u0026gt;: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Seek Net-New Opportunities: \u0026lt;/strong\u0026gt;Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Communicate Tailored Value: \u0026lt;/strong\u0026gt;Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Partner Cross-Functionally: \u0026lt;/strong\u0026gt;Align Sales, Operations, Product, Finance, Trust \u0026amp;amp; Safety and Support around client priorities and optimize our offerings to their needs\u0026lt;strong\u0026gt;.\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;Lead Pricing Discussions: \u0026lt;/strong\u0026gt;Lead renewals and expansions, including structured negotiations and closing motions\u0026lt;strong\u0026gt;.\u0026lt;/strong\u0026gt;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;\u0026lt;strong\u0026gt;AI Enabled Operational Excellence: \u0026lt;/strong\u0026gt;Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications.\u0026amp;nbsp;Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Required\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;8+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven ownership of retention and expansion revenue.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Strong executive communication and presentation skills.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Demonstrated success managing complex, multi-stakeholder accounts.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Advanced CRM discipline and data fluency (Salesforce or equivalent).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience leading cross-functional account execution.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Comfort operating in ambiguity with accountability for outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience in education, government, or regulated markets highly preferred\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Familiarity with Challenger or similar insight-led sales methodologies highly preferred\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Background in transportation, logistics, or marketplace platforms highly preferred\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;High operational rigor and the ability to leverage AI into daily workflows\u0026amp;nbsp;\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $90,000-100,000 base with an OTE of $150,000 - $170,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal-opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;NOTE* The role will require 2-3 days on-site client visits regionally.\u0026amp;nbsp;\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4017328004,"name":"Sales","child_ids":[],"parent_id":4103597004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]},{"absolute_url":"https://job-boards.greenhouse.io/hopskipdrive/jobs/6002665004","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":5157613004,"location":{"name":"Remote USA"},"metadata":null,"id":6002665004,"updated_at":"2026-05-29T22:43:35-04:00","requisition_id":"581","title":"VP, Engineering","company_name":"HopSkipDrive","first_published":"2026-05-29T22:42:42-04:00","language":"en","application_deadline":null,"content":"\u0026lt;div class=\u0026quot;content-intro\u0026quot;\u0026gt;\u0026lt;p\u0026gt;At \u0026lt;a href=\u0026quot;https://www.hopskipdrive.com/\u0026quot;\u0026gt;HopSkipDrive\u0026lt;/a\u0026gt;,\u0026amp;nbsp;our mission is to create opportunity for all through mobility. We\u0026#39;re\u0026amp;nbsp; the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;Founded by three moms as a solution to their own transportation challenges, we\u0026#39;ve now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a \u0026lt;em\u0026gt;Series D company and has raised $100M to date.\u0026lt;/em\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;How we work\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don\u0026#39;t expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We\u0026#39;re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.\u0026lt;/p\u0026gt;\u0026lt;/div\u0026gt;\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who We Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive\u0026#39;s Product \u0026amp;amp; Technology organization is the heart of our competitive advantage, building the technologies that have and continue to transform student transportation. Our applications span web and mobile, B2B and B2C, operational and transformational. We embrace the power of AI to allow us to deliver more value to our customers faster, while keeping humans at the center of our work. Our teams operate through shared ownership and close collaboration rather than functional handoffs. We value leaders who can navigate complex tradeoffs across customer experience, operational realities, technical scalability, and long-term platform health.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;As the VP of Engineering, you will lead our engineering organization through its next phase of scale and development. Partnering closely with the Chief Product \u0026amp;amp; Technology Officer (CPTO) and the SVP of Product, you will drive execution, foster a high-performance culture, and lead our transition toward an AI-accelerated engineering environment.\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;Lead and scale a high-performing engineering organization by building deep trust, diagnosing organizational strengths, and establishing the career growth paths and structural changes required to elevate performance.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Engage deeply and credibly in system design and architecture discussions, helping senior engineers navigate complex technical trade-offs across our platform (Ruby on Rails, React, iOS/Android), service boundaries, and modern infrastructure investments.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Pioneer the integration of AI and agentic capabilities into our software development lifecycle, spanning the evaluation of new technical infrastructure, coaching teams through change management, and establishing the workflows, testing methodologies, and QA guardrails required to safely accelerate shipping velocity.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Own the Engineering department\u0026#39;s delivery and operational excellence, ensuring predictable, high-quality execution, world-class reliability, and continuous improvement of technical health and process discipline.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Partner closely with the CPTO, SVP of Product, Design, Data, and Operations to align product vision with technical strategy and drive unified customer and business outcomes.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Manage the engineering department\u0026#39;s fiscal health, including headcount, contractors, software, and infrastructure budgets.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Who You Are\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;You are a seasoned engineering leader who has stayed close to the technology and understands how to navigate organizational growth with empathy and clarity. You possess the strategic vision to lead an engineering department into its next phase of maturity while maintaining a deep, credible connection to the architecture and tech stack.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;What You Bring:\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;ul\u0026gt;\n\u0026lt;li\u0026gt;Deep technical credibility rooted in the ability to engage constructively in architecture, system design, and engineering quality discussions as a collaborative peer to senior engineers and technical leaders.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Breadth across modern web, mobile, cloud, and marketplace-oriented\u0026amp;nbsp; environments, with the ability to reason across Ruby on Rails, React, native iOS and Android clients, and modern cloud infrastructure (AWS or GCP).\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Experience evolving developer workflows to leverage automation and AI agents, with a fluent understanding of how these tools impact code quality, security, and velocity, and a proven track record of successfully driving developer adoption.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Proven leadership at scale, including experience managing engineering managers, designing organizational structures for teams of 30-60 engineers, and making deliberate talent decisions to optimize team health.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Thoughtful change leadership and the resilience to drive organizational or cultural shifts with empathy, clarity, and a proven ability to bring skeptical teams along.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Business and product centricity, with a history of balancing technical hygiene, reliability, architecture investments, operational realities, and near-term customer and business needs.\u0026lt;/li\u0026gt;\n\u0026lt;li\u0026gt;Excellent asynchronous communication skills, emphasizing clear written documentation and structured delegation that empowers remote engineering teams to operate with high autonomy.\u0026lt;/li\u0026gt;\n\u0026lt;/ul\u0026gt;\n\u0026lt;p\u0026gt;\u0026lt;strong\u0026gt;Our Investment In You\u0026lt;/strong\u0026gt;\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $240,000 - $270,000 + bonus. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;HopSkipDrive is proud to be an equal opportunity employer.\u0026amp;nbsp; All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;* This role will be fully remote in one of the following states \u0026lt;strong\u0026gt;AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI\u0026lt;/strong\u0026gt;**\u0026lt;/p\u0026gt;\n\u0026lt;p\u0026gt;\u0026amp;nbsp;\u0026lt;/p\u0026gt;","departments":[{"id":4017329004,"name":"Engineering","child_ids":[],"parent_id":4103599004}],"offices":[{"id":4009959004,"name":"Remote","location":null,"child_ids":[],"parent_id":null}]}],"meta":{"total":13}}