Director of Legal Risk & Regulatory Strategy, HopSkipDrive
Safe youth transportation solution
Be an early applicant
Safe youth transportation solution
501-1000 employees
Be an early applicant
501-1000 employees
Company mission
To create opportunity for all through mobility.
Role
Who you are
- You are a strategic legal and regulatory leader who thrives in high-growth environments where the challenge is to build what does not yet exist. You are energized by solving complex systems problems, navigating ambiguity, and creating scalable frameworks that enable innovation. You bring the depth of experience needed to shape company-wide regulatory strategy, paired with the agility to operate in a fast-moving, scaling tech environment
- 10+ years of legal experience, with significant expertise in compliance and at least 5 years managing litigation or claims portfolios
- Demonstrated success designing and operationalizing compliance systems in a fast-growing or multi-jurisdictional environment—Big Tech or highly regulated tech preferred
- Experience advising executives and influencing strategy in environments where regulatory requirements intersect with product, operations, and growth
- Deep understanding of TNC, DOE, or other regulatory frameworks involving minors—or the ability to quickly become a subject-matter expert
- Proven ability to manage audits, implement governance controls, and translate complex regulations into practical business processes
- Experience building and leading teams, with an orientation toward systems, empowerment, and scalable processes
- Highly analytical, a strong communicator, and comfortable operating at both strategic and tactical levels
- A bias for action and adaptability as regulations, markets, and the business evolve rapidly
What the job involves
- HopSkipDrive's Legal & Regulatory team is scaling rapidly to support the next phase of company growth, operational complexity, and national expansion. As a transportation network company operating in a highly regulated and safety-critical environment, we are building the foundational systems, strategic insights, and compliance infrastructure that will support multi-state scale
- As Director, Legal Risk & Regulatory Strategy, you will help architect these systems. You will shape how a fast-growing technology company proactively manages litigation, aligns regulatory strategy with product and operations, and builds durable frameworks that support long-term scalability
- Build and lead the strategic roadmap for regulatory compliance across TNC and education-focused requirements, ensuring we scale responsibly and efficiently
- Own the company’s litigation and claims portfolio, building systems for early risk detection, streamlined management, and high-quality outcomes
- Partner deeply with senior leadership, Product, Operations, and cross-functional teams to anticipate regulatory shifts and inform company-wide strategy
- Develop and operationalize compliance programs, policies, audits, and controls in a way that is built for scale and automation—not manual lift
- Lead, mentor, and grow a team of compliance managers focused on market-level or client-specific compliance operations
- Build repeatable, data-driven processes for monitoring regulatory change, surfacing insights, and enabling leadership decision-making
- Serve as a subject-matter expert on TNC and DOE regulations, ensuring alignment between emerging business models and the regulatory landscape
- Drive cross-functional initiatives that reduce operational risk, strengthen governance, and prepare the organization for multi-state and multi-product growth
Our take
Across the US, school transportation is under pressure as driver shortages, budget cuts, and rigid bus routes are making it harder for students to get to school safely and on time. This has opened the door for smaller vehicles and ride-hailing services to step in and support those students who don't fit neatly into traditional routes. HopSkipDrive has grown within this space, offering a flexible alternative that helps schools fill these gaps.
HopSkipDrive connects children with carefully vetted caregivers (often grandparents, nurses or childcare processionals) who then provide reliable rides when buses or public transport falls short. Operating in 17 states and supporting over 10,000 schools, the services has certainly eased commutes for many families.
And now the company is focsued on strenghtening its impact with technology and innovation. With its RouteWise AI platform it helps districts cut costs, improve efficiency and manage driver shortages, all while new safety modules and AI-driven planning tools continue to raise industry standards. With these advancements and a growing network of partners, the company is ready to keep shaping a more flexible futur for school transportation.
Freddie
Company Specialist at Welcome to the Jungle
Insights
23% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Sep 2022
$37m
SERIES D
Aug 2021
$25m
SERIES C
Total funding: $107m
Company benefits
- Medical, Dental & Vision
- Health Spending Account
- Mental Health Resources
- Employee Assistance Program
- Short- & Long-Term Disability Insurance
- Paid Parental Leave
- 401K Plan
- Company Ownership/Equity
- Medical & Dependent Care FSA
- Travel Insurance
- Supplemental Legal
- Fully Remote Work Option
- Flexible Time Off
- 11 Annual Paid Holidays
- Week Closure at End of Year
- Sick Time Off for You and Family
- Home Internet Reimbursement
- Professional Development & Learning Stipend
- Remote & In-Person Quarterly Team Events
- Internal Rewards & Recognition Program
- Employee Referral Bonuses
Company HQ
Little Tokyo, Los Angeles, CA
Leadership
Joanna McFarland
(Co-Founder & CEO)Former Board Member at the Marketplace Industry Association and LA Tech.org.
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