Director, Legal Risk & Regulatory Strategy

At HopSkipDrive, our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

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.

You will:

• 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.

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.

With the following experience, you’ll make an immediate impact:

• 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.