VP, Legal

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 & External Affairs team plays a critical role in enabling rapid growth while mitigating risk and ensuring the highest standards of safety and compliance. As a strategic partner to all teams across the business, we design scalable legal, regulatory, and compliance frameworks to support HopSkipDrive’s expanding marketplace operations. As we continue to grow our national footprint and navigate complex legal and commercial landscapes, we’re excited to welcome a Vice President of Legal who will shape the future of our legal function and serve as a trusted advisor to the executive team by:

• Serving as a key legal advisor to the Chief Legal and Corporate Affairs Officer as well as the executive leadership team
• Leading HopSkipDrive’s legal function through strategic planning, budget oversight, managing team accountability, and supporting team development You’ll also be responsible for building scalable legal infrastructure, including contracting systems, playbooks, and workflows, to increase speed and consistency across the organization
• Overseeing all legal functions by playing a lead role in setting the strategic vision in partnership with the legal directors, with a particular focus on commercial (vendor and B2B agreements), product, regulatory affairs & compliance, and insurance and litigation
• Directing corporate legal matters, including governance, risk management, and entity structuring in partnership with external counsel
• Overseeing the compliance function, supporting legal directors in ensuring robust controls across data privacy, regulatory filings, and internal policies.
• Collaborating closely with cross-functional partners in Policy, Communications, and Safety to support strategic initiatives, while ensuring legal and reputational risk is well-managed
• Partnering cross-functionally with GTM, Finance, Product, and People teams to anticipate and address legal issues in a fast-paced, marketplace-driven, highly regulated, and public-sector facing environment
• Leading and developing a high-performing legal team of 10, while managing outside counsel relationships in alignment with business priorities and budget discipline.

Who You Are

You’re a strategic and collaborative legal leader with deep experience in commercial contracts and compliance. You thrive in fast-paced, scaling environments and know how to translate legal risk into actionable, business-minded decisions. You’re passionate about mentoring others and building systems that support long-term success, and with the following skills, you’ll make a tangible and immediate impact:

• 15+ years of legal experience with a strong in-house track record at high-growth, marketplace or platform-based companies, marketplace company experience strongly preferred
• Juris Doctorate and active bar membership in at least one U.S. jurisdiction
• Demonstrated leadership across commercial and/or compliance legal areas inclusive of document and contract preparation and review of vendor/supplier agreements, customer/sales agreements; corporate legal experience a strong plus.
• Experience building commercial legal processes and partnering across functions including – but not limited to – IT, People Teams and Go-To-Market as to support business scaling
• Proven ability to oversee compliance programs including privacy, data handling, and regulatory frameworks
• Strong management skills, including hiring, mentoring, and guiding legal teams and external counsel
• Comfortable operating in ambiguity with strong judgment, prioritization, and execution skills
• Based anywhere in the U.S. with preference for candidates located in Los Angeles or Chicago

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The base salary range for this role is $240,000 - $260,000. The total compensation package for this role also includes equity stock options and a target bonus. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

• This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI