Senior Counsel – Policy & Regulatory

HopSkipDrive

Senior Counsel overseeing regulatory compliance and litigation at HopSkipDrive, a leader in student transportation. Managing legal obligations and engaging with legislation in transportation.

Posted 7/7/2026full-timeRemote • Arizona, California, Colorado, District of Columbia, Florida, Illinois, Kansas, Maryland, Massachusetts, Minnesota, Missouri, Montana, Nevada, New Jersey, New Mexico, New York, North Carolina, Oklahoma, Oregon, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, Wisconsin • 🇺🇸 United StatesSenior💰 $178,000 - $200,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Expertise in regulatory compliance and legal analysis within the transportation sector, with a strong focus on AI tools and legislative processes. Proven ability to manage complex regulatory portfolios and advise cross-functional teams on compliance and policy implications.

Highest-signal resume keywords

J.D. From An Accredited Law School8+ Years Of Legal ExperienceRegulatory Compliance ExpertiseAI Tools Proficiency In Legal ContextExceptional Analytical Skills

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Regulatory ComplianceLitigation ManagementLegal ResearchContract AnalysisLegislative AnalysisClaims ManagementPolicy DevelopmentBill DraftingPublic Records ManagementTNC Licensing

Soft Skills

Excellent Written CommunicationOral Communication SkillsStrong Organizational SkillsCollaboration Across TeamsAbility To Work In Fast-Paced Environments

Tools & Technologies

AI ToolsMatter Management SystemsRegulatory Analysis SoftwareDocument Management SystemsData Use Agreements

Certifications & Qualifications

Active License To Practice Law

Industry Keywords

Transportation Network CompanySchool Pupil TransportationGig Economy ClassificationState Regulatory AgenciesAdministrative Proceedings

About the role

Key responsibilities & impact

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.
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 local agencies.
Leverage AI tools for more efficient legislative analysis.
Oversee a book of claims related to labor and employment claims.
Manage a small number of cases or claims related to civil litigation including discovery strategy, preparing corporate witnesses, and directing litigation defense.
Support outside counsel in preparing for and conducting arbitrations.
Handle subpoenas, service of process, and regulatory investigations, coordinating with outside counsel as appropriate.
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 growing 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

What you’ll need

J.D. from an accredited law school and active license to practice law in the jurisdiction where you live.
8+ years of legal experience, including at 5 in a law firm or in-house role, with primary focus on regulatory and/or governmental affairs and meaningful exposure to litigation or claims management.
Demonstrated ability to work with AI tools in a legal context and uses AI consistently in their own legal work, whether for contract analysis, legal research and synthesis, matter management, regulatory analysis, or various projects.
Demonstrated experience navigating state regulatory agencies, administrative proceedings, or legislative processes
Proven ability 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 varied audiences and collaborate effectively across teams
Strong organizational skills and the ability to manage a high-volume, rapidly evolving regulatory portfolio with competing deadlines
Comfort operating in a fast-paced, ambiguous environment — bonus points for experience at a rapidly growing company.

Benefits

Comp & perks

equity
flexible vacation
medical, dental, vision and life insurance
401(k)
FSA
opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential