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Director, Commercial Law

HopSkipDriveRemoteLegal & Corporate Affairs (Business Unit)
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Salary
Not listed
Job type
Full-time
Work mode
Remote
Posted
24 Aug 2026
Status
Open · checked 7d ago

About this role

HopSkipDrive is seeking a remote Director, Commercial Law to lead legal initiatives and modernize contracting processes using artificial intelligence. This position is ideal for a seasoned attorney with extensive commercial contracting and people-management experience who wants to make a measurable impact in a growing tech company.

Role Overview

The Director, Commercial Law will serve as a trusted advisor and business partner, working hand-in-hand with leaders across HopSkipDrive to support strategic initiatives, innovation, and growth. Reporting to the VP, Legal, this role involves navigating complex legal landscapes, mitigating risks, and protecting intellectual property and financial interests. The position requires a systems-oriented approach to modernize legal operations through the integration of artificial intelligence and contract lifecycle management platforms.

Key Responsibilities

Revamp and revitalize the contract review process for efficiency with a strong focus on AI integration.
Oversee and manage the complete contract lifecycle from initiation, drafting, and negotiation to execution and termination.
Perform high-volume contract review to ensure absolute accuracy and compliance with legal requirements and company policies.
Manage vendor contracts by negotiating terms, monitoring performance, and resolving potential disputes.
Lead, scale, and mentor a team of direct and skip-level reports in a fast-paced environment.
Collaborate directly with enterprise revenue teams to support business development and sales efforts.
Design, build, and deploy AI tools and agents to automate contract intake, redlining, drafting, risk flagging, and clause extraction.
Evaluate, select, and implement legal AI and contract lifecycle management platforms while owning vendor relationships and integrations.
Extend AI adoption into other legal functions such as compliance, privacy, and eDiscovery or litigation support.
Define and track efficiency and quality metrics to demonstrate the return on investment of AI initiatives to leadership.

Requirements

Possess a Juris Doctor (JD) degree from an accredited Law School.
Hold an active Bar Membership in good standing and a license to practice law.
Bring 10 or more years of experience working within an in-house legal team or a law firm.
Have 10+ years of experience drafting, negotiating, and reviewing a wide variety of commercial contracts, including service contracts, vendor agreements, NDAs, and licensing agreements.
Demonstrate hands-on experience implementing or configuring GenAI and AI tools for legal work, including prompt engineering and tuning AI agents.
Possess experience evaluating and implementing CLM platforms or legal AI tools like Ironclad, Ivo, Harvey, Spellbook, or Legora.
Understand AI governance and regulatory considerations such as data privacy requirements and the EU AI Act.
Show a proven track record of people management, mentoring, and supporting direct reports.

Skills and Tools

Commercial contract drafting and negotiation
AI tool configuration, prompt engineering, and GenAI implementation
Contract Lifecycle Management (CLM) platform evaluation and management
Vendor management and dispute resolution
AI governance and data privacy regulatory knowledge
Cross-functional collaboration and stakeholder communication

Salary and Benefits

Salary range for this role in Los Angeles, CA is $189,000.00 - $200,000.00, with final compensation determined by location, relevant experience, and skill set.
Full-time employees receive equity stock options as part of the total compensation package.
Comprehensive health benefits including medical, dental, vision, and life insurance.
Financial and retirement benefits such as a 401(k) and Flexible Spending Account (FSA).
Flexible vacation policy and the opportunity to work in a drug-free workplace.

About the Company

HopSkipDrive is the leader in safe, fast, and simple supplemental student transportation, connecting children with highly vetted caregivers through an innovative marketplace and software platform. Founded by three moms to solve real transportation challenges, the company has facilitated over five million rides across more than 20 states. Recognized frequently on the Inc. 5000 and Deloitte fast-growing technology lists, HopSkipDrive is a Series D, VC-backed company that has raised $100 million to date and weaves artificial intelligence into work at every level.

How to Apply

Interested candidates should apply directly on the official HopSkipDrive careers page.

Questions candidates ask

What is the location requirement for the Director, Commercial Law position?

This position is fully remote and can be performed from one of the following eligible 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, or WI.

What qualifications are required for this legal role?

Candidates must hold a Juris Doctor (JD) from an accredited law school, maintain an active bar membership in good standing, and have 10+ years of experience working in a law firm or in-house legal team.

What kind of experience with artificial intelligence is necessary?

Applicants need hands-on experience configuring or implementing GenAI and AI tools for legal work, building or tuning AI agents for contract review and negotiation, prompt engineering, and understanding AI governance and regulatory frameworks.

What is the salary range for the role?

The salary range for the role in Los Angeles, CA is $189,000.00 to $200,000.00, with final compensation varying based on location, experience, certifications, and skill set.

What additional benefits are included with the position?

Full-time employees receive equity stock options, flexible vacation, medical, dental, vision and life insurance, a 401(k), and an FSA.

Ready to apply?

The application is on the official HopSkipDrive careers page.

Apply on company site