Sr Counsel - Policy & Regulatory

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 company regulations.