[Hiring] Director of Commercial Law @HopSkipDrive

Role Description

The Legal team works hand-in-hand with leaders across the company to support HopSkipDrive’s growth, innovation, and strategic initiatives. This is an exciting opportunity to learn in a fast-paced environment and own high-priority projects.

• 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.
• 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.
• Defining and tracking efficiency and quality metrics (e.g., cycle time, accuracy, cost savings) to demonstrate measurable ROI from AI initiatives.

Qualifications

• 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.
• Hands-on experience implementing or configuring AI/GenAI tools for legal work.
• Experience evaluating and implementing legal AI or contract lifecycle management (CLM) platforms.
• Working knowledge of AI governance and regulatory considerations.
• A track record of people-management, and success in mentoring and supporting direct reports.
• Strong communication and legal skills to counsel internal stakeholders.
• Ability to efficiently and strategically manage all commercial contracting processes.
• A solutions-oriented mindset with a focus on helping business partners solve problems.

Requirements

• Comfort and familiarity working closely with key partners throughout the company.
• Ability to spearhead projects that make an immediate impact on our fast-growing, dynamic business.
• Design processes to automate and streamline high-velocity work.

Benefits

• Equity for every full-time employee.
• Flexible vacation.
• Medical, dental, vision, and life insurance.
• 401(k) and FSA.
• Opportunity to work for a uniquely positioned, VC-backed company.
• Salary range for this role in Los Angeles, CA is $189,000.00 - $200,000.00.
• Fully remote position available in multiple states.

Company Description

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Founded by three moms, we've facilitated more than five million rides across over 20 states and continue to grow rapidly.