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HopSkipDrive

Director Legal, Commercial & Product

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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

The Legal  team works hand-in-hand with leaders across the company to support HopSkipDrive’s growth, innovation, and strategic initiatives. It's an integral and highly impactful team that provides legal advice and guidance to ensure the company operates within legal boundaries while protecting intellectual property, financial interests, and regulatory compliance.  We navigate complex legal landscapes to mitigate risks and support innovation.  This is an exciting opportunity to learn in a fast-paced environment and own high-priority projects.


  • Overseeing and managing the entire contract lifecycle, from initiation and drafting to negotiation, execution, and termination.
  • Performing high-volume contract review, ensuring contracts are accurate, complete, and comply with company policies and legal requirements.
  • Managing vendor contracts, including negotiating terms, monitoring performance, and resolving disputes.
  • Leading and scaling teams in a fast-paced, high-growth environment, adapting quickly to changing business needs.
  • Managing a team of direct reports and skip-level reports, providing guidance, feedback, and development opportunities.
  • Collaborating with enterprise revenue teams to support sales and business development efforts.
  • Working effectively under pressure with demanding stakeholders, balancing competing priorities and meeting tight deadlines.
  • Maintaining a systems-oriented, process-driven approach to contract management, identifying opportunities for efficiency and automation.


Who You Are

You’re a seasoned attorney with a knack for collaboration and influence, and a proven people manager.  You are looking for an opportunity to serve as a trusted advisor and business partner, fostering strong relationships across the organization and externally.  Reporting to the VP, Legal who leads the company’s legal functions and with the following skills, you’ll make a tangible and immediate impact:


  • Juris Doctor (JD)  from an accredited Law School
  • Bar Membership in good standing and licensed to practice Law
  • 10+ years of experience working for an in-house legal team, preferably in the technology sector
  • 8+ years experience drafting, reviewing, and negotiating a wide range of commercial contracts, including vendor agreements, service contracts, NDAs, and licensing agreements
  • A track record of people-management, and success in mentoring and supporting direct reports
  • Strong communication and legal skills to counsel internal stakeholders on contractual risks, obligations, and potential liabilities
  • Comfort and familiarity working closely with key partners throughout the company to close high-value deals and bring new products to market
  • Ability to efficiently and strategically manage all commercial contracting processes, support product development, manage privacy law, and collaborate with key stakeholders to align business strategies with legal requirements
  • Ability to spearhead projects that make an immediate impact on our fast-growing, dynamic business, and design processes to automate and streamline high-velocity work
  • A solutions-oriented mindset with a focus on helping business partners solve problems and overcome obstacles

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 committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is 185,000 - 200,000. 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, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI**

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