Director, Commercial Law

About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across 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 over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

How we work

We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.

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. The team is embracing AI as a core part of how we work, and is investing in building AI agents and other legal tech tools to modernize contracting and other legal functions.

What You’ll Do

• Revamping and revitalizing the contract review process for efficiency with a focus on AI use.
• 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.
• Designing, building, and deploying AI tools and/or agents to automate contract intake, drafting, redlining, clause extraction, and risk flagging, partnering with engineering and legal operations to continuously tune models, playbooks, and guardrails.
• Evaluating, selecting, and implementing legal AI and contract lifecycle management (CLM) platforms, and owning vendor relationships, integrations, and performance metrics.
• Extending AI adoption beyond contracts into other legal functions, such as compliance, privacy, and litigation support/eDiscovery, identifying additional opportunities for automation and efficiency.
• Defining and tracking efficiency and quality metrics (e.g., cycle time, accuracy, cost savings) to demonstrate measurable ROI from AI initiatives and reporting progress to legal and business leadership.

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 or law firm.
• 10+ years experience drafting, reviewing, and negotiating a wide range of commercial contracts, including vendor agreements, service contracts, NDAs, and licensing agreements
• Hands-on experience implementing or configuring AI/GenAI tools for legal work, such as building or tuning AI agents for contract review, drafting, or negotiation, prompt engineering, and evaluating model outputs for accuracy and risk
• Experience evaluating and implementing legal AI or contract lifecycle management (CLM) platforms (e.g., Ironclad, Ivo, Harvey, Spellbook, Legora, or similar), including vendor management and system integrations
• Working knowledge of AI governance and regulatory considerations (e.g., the EU AI Act, state-level AI laws, and data privacy requirements) as applied to legal AI tools
• 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $189,000.00 - $200,000.00. 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 **