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 local agencies.

Leverage AI tools for more efficient legislative analysis.

Litigation

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.

Cross-Functional Advisory

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.

Leverage AI-powered tools to increase efficiency across the compliance portfolio, and advise the business on legal exposure from emerging federal and state AI policy developments.

What You’ll Bring

Required

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

Preferred

Exposure to litigation or claims management, especially answering discovery and drafting court filings, and/or preparing corporate representatives for testimony.

Experience in transportation, mobility, gig economy, or a similarly regulated industry.

Familiarity with public utilities commissions and/or transportation and education regulatory frameworks.

Experience advising on automated decision-making, AI governance, or algorithmic compliance.

Background in data privacy (CCPA, HIPAA) or government contracting.

Exposure to multi-state compliance programs or regulatory tracking systems.

Hands-on experience working with AI tools for legal or compliance purposes, or a demonstrated interest in building AI competency as a core part of your legal practice.

Who You Are

You build credibility fast. Government agencies, school districts, and internal partners take you seriously because you are prepared, responsive, and direct.

You don’t wait to be asked. You spot a compliance gap or a bill moving through committee and you’re already drafting the memo.

You can hold complexity without losing the thread. Multi-state, multi-agency, multi-stakeholder — you manage it without drama.

You’re curious about AI and legal technology and see tools like AI-assisted research and contract automation as part of how modern legal