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.
Responsibilities
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.
Advises internal stakeholders on regulatory requirements for new market entry and ongoing compliance obligations in existing markets.
Manage a small 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.
Oversee AI projects and workflows related to regulatory matters.
Oversee 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.
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.
Requirements
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.