Sr Counsel

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.

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 least 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.

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.