Sr Counsel - Policy & Regulatory

About the role

HopSkipDrive is seeking a Senior Counsel to manage a significant portion of the company's regulatory compliance efforts. This role involves leading engagement on legislation impacting operations, overseeing a portfolio of legal cases, and advising cross-functional teams on complex compliance matters.

Key facts

What you'll do

• Oversee multi-state regulatory compliance for a transportation network company focused on student transport, including licensing, driver standards, and state-specific regulations.
• Prepare and submit regulatory filings, manage agency communications, and advise on contract provisions with regulatory implications.
• Monitor and analyze federal and state legislation affecting transportation network companies and school transportation.
• Develop legal and policy stances on proposed legislation and collaborate on engagement strategies.
• Manage a portfolio of legal claims, including labor and employment matters, and oversee litigation defense.
• Provide legal guidance on data use agreements and research partnerships.
• Act as a subject matter expert on AI and automated decision-making, advising on compliance with emerging AI legislation.
• Utilize AI tools to enhance efficiency in legal and compliance work.

Requirements

• Juris Doctor degree from an accredited law school and an active law license.
• A minimum of 8 years of legal experience, with at least 5 years in a law firm or in-house setting, focusing on regulatory affairs or government relations, and experience managing litigation or claims.
• Demonstrated experience working with and consistently using AI tools in legal contexts such as research, contract analysis, or regulatory analysis.
• Proven track record of navigating state regulatory agencies, administrative proceedings, or legislative processes.
• Ability to advise internal teams on regulatory requirements and policy implications.
• Strong analytical skills to interpret and apply complex regulations to business operations.
• Excellent written and verbal communication abilities for diverse audiences.
• Proficient organizational skills to manage a high-volume, evolving regulatory portfolio with competing deadlines.
• Comfort working in a fast-paced and ambiguous environment.

Nice to have

• Experience with litigation, including discovery and drafting court filings, or preparing witnesses for testimony.
• Background in transportation, mobility, the gig economy, or a similarly regulated industry.
• Familiarity with public utility commissions or transportation and education regulatory frameworks.
• Experience advising on AI governance or algorithmic compliance.
• Knowledge of data privacy regulations (e.g., CCPA, HIPAA) or government contracting.
• Experience with multi-state compliance programs or regulatory tracking systems.

Skills & tools

• AI tools for legal and compliance work.

Practical notes

• Salary range: $178,000.00 - $200,000.00 annually, with final compensation based on location, experience, and skills.
• Total compensation includes equity stock options.
• Benefits include flexible vacation, medical, dental, vision, and life insurance, 401(k), and FSA.
• HopSkipDrive operates as a drug-free workplace.
• Equal opportunity employer.