Sr Counsel - Policy & Regulatory

About HopSkipDrive At HopSkipDrive, our mission is to create opportunity for all through mobility. We're 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. Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. 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 Series D company and has raised $100M to date. How we work We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before. About the Role HopSkipDrive is seeking a Senior Counsel, Regulatory & Litigation to own a significant portion of the company’s state and federal regulatory compliance program, lead engagement on legislation that shapes how we operate, and manage a litigation portfolio from onset to resolution. This is a high-visibility role for a lawyer who thrives at the intersection of policy and operations, builds credibility quickly with government agencies and internal partners alike, knows how to translate complex regulatory requirements into practical compliance strategies, and can oversee a litigated case. You will manage HopSkipDrive’s regulatory obligations across multiple jurisdictions — monitoring the legislative landscape, managing filings and agency relationships, advising cross-functional teams on compliance, and positioning the company to respond to audits, public records requests, and enforcement actions. You will also contribute to emerging areas including AI policy, data sharing, and government contracting compliance. On the litigation end, you will oversee a small book of claims and litigation related to driver union and other civil matters. What You’ll Do Regulatory Compliance & Licensing Own multi-state regulatory compliance obligations for HopSkipDrive as a transportation network company operating in the education sector, including TNC licensing, driver qualification standards, DMV record check requirements, and state-specific transportation regulations. Draft and submit regulatory filings, advice letters, and compliance attestations to state agencies; track and manage agency review, approval, and disposition. Advise on revenue contract and RFP provisions with regulatory implications, including background check requirements, reporting obligations, and driver and vehicle standards. Advise internal stakeholders on regulatory requirements for new market entry and ongoing compliance obligations in existing markets. Build AI projects and workflows related to regulatory matters. Legislative Affairs & Policy Monitor and analyze federal and state legislation affecting HopSkipDrive’s operations, with a focus on transportation network companies, school pupil transportation, and automated decision systems. Develop legal and policy positions on pending legislation; collaborate with the Policy and Government Relations teams to prepare bill analyses, public comments, and engagement strategies. Assist with bill review and bill drafting in partnership with the Policy team. Identify legislative trends and develop proactive compliance strategies, particularly around TNC regulation, school transportation, and gig economy classification. Represent HopSkipDrive’s interests in regulatory rulemakings before state public utility commissions and transportation agencies. Monitor and manage responses to public records and disclosure requests from state and…