Senior Counsel, Policy & Regulatory

Responsibilities

• Own multi-state regulatory compliance obligations including TNC licensing and driver qualification standards
• Draft and submit regulatory filings, advice letters, and compliance attestations to state agencies
• Monitor and analyze federal and state legislation affecting transportation and school pupil transportation
• Develop legal and policy positions on pending legislation and prepare bill analyses
• Oversee a book of claims related to labor, employment, and civil litigation
• Manage discovery strategy, corporate witnesses, and direct litigation defense
• Serve as a legal subject matter expert on AI and automated decision-making compliance
• Manage data use agreements and research partnerships

Requirements

• J.D. from an accredited law school and active license to practice law
• 8+ years of legal experience, with at least 5 years in a law firm or in-house role
• Primary focus on regulatory or governmental affairs with exposure to litigation
• Demonstrated ability to use AI tools consistently in legal work
• Experience navigating state regulatory agencies or legislative processes
• Exceptional analytical and communication skills

Preferred Qualifications

• Experience in transportation, mobility, or the gig economy
• Familiarity with public utilities commissions or education regulatory frameworks
• Experience advising on AI governance or algorithmic compliance
• Background in data privacy (CCPA, HIPAA) or government contracting
• Exposure to multi-state compliance programs

About the Company

HopSkipDrive is a Series D company and the leader in safe, supplemental student transportation. We connect kids to highly-vetted caregivers through our marketplace and software to solve transportation challenges for schools and districts across the country.