Senior Counsel – Policy & Regulatory

This is a fully remote position, open to applicants in Arizona, +25 more states.

📋 Description

• Take ownership of multi-state regulatory compliance responsibilities for HopSkipDrive as a transportation network company in the education sector, including TNC licensing, driver qualification standards, DMV record check requirements, and state-specific transportation regulations.

• Prepare and submit regulatory filings, advice letters, and compliance attestations to state agencies; track and oversee agency review, approval, and outcomes.

• Provide guidance on revenue contracts and RFP provisions that have regulatory implications, including background check requirements, reporting obligations, and standards for drivers and vehicles.

• Advise internal stakeholders on regulatory obligations for entering new markets and maintaining compliance in existing markets.

• Develop AI projects and workflows related to regulatory issues.

• Monitor and evaluate federal and state legislation impacting HopSkipDrive’s operations, with a focus on transportation network companies, school pupil transportation, and automated decision-making systems.

• Formulate legal and policy positions on proposed legislation; work with the Policy and Government Relations teams to prepare bill analyses, public comments, and engagement strategies.

• Assist in bill review and drafting in collaboration with the Policy team.

• Identify legislative trends and create proactive compliance strategies, particularly regarding TNC regulation, school transportation, and gig economy classification.

• Represent HopSkipDrive’s interests in regulatory rulemakings before state public utility commissions and transportation agencies.

• Oversee and manage responses to public records and disclosure requests from state and local agencies.

• Utilize AI tools for more efficient legislative analysis.

• Manage a portfolio of claims related to labor and employment issues.

• Handle a limited number of cases or claims concerning civil litigation, including developing discovery strategies, preparing corporate witnesses, and directing litigation defense.

• Support outside counsel in preparing for and conducting arbitrations.

• Manage subpoenas, service of process, and regulatory investigations, coordinating with outside counsel as necessary.

• Build AI projects and workflows related to litigation.

• Manage data use agreements and research partnerships with academic institutions and government agencies.

• Provide legal research and rulemaking assistance as needed to support a busy and expanding regulatory portfolio.

• Serve as a legal subject matter expert on AI and automated decision-making, advising on compliance with emerging state AI legislation and internal AI governance frameworks.

⛳️ Requirements

• J.D. from an accredited law school and an active license to practice law in your jurisdiction.

• 8+ years of legal experience, including at least 5 years in a law firm or in-house role, primarily focused on regulatory and/or governmental affairs with significant exposure to litigation or claims management.

• Proven ability to work with AI tools in a legal context and consistently utilize AI in their own legal work, whether for contract analysis, legal research and synthesis, matter management, regulatory analysis, or various projects.

• Demonstrated experience in navigating state regulatory agencies, administrative proceedings, or legislative processes.

• Established capability to advise cross-functional teams on legislative and regulatory requirements and the legal implications of policy priorities.

• Exceptional analytical skills with the ability to interpret complex regulatory requirements and apply them to practical business operations.

• Excellent written and oral communication skills, with the ability to present information clearly to diverse audiences and collaborate effectively across teams.

• Strong organizational skills and the ability to manage a high-volume, rapidly changing regulatory portfolio with competing deadlines.

• Comfort in a fast-paced, ambiguous environment — bonus points for experience at a rapidly growing company.

🏝️ Benefits

• Equity

• Flexible vacation

• Medical, dental, vision, and life insurance

• 401(k)

• FSA

• Opportunity to work for a uniquely positioned, VC-backed company in a highly attractive space with significant upside potential