SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
HopSkipDrive is a Series D marketplace platform connecting students with vetted caregivers for supplemental transportation, operating across 20+ states and having facilitated over 5 million rides. The company has raised $100M and is recognized on the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists.
As Director of Commercial Law, you will lead the legal team's commercial contracting function and report to the VP of Legal. This is a high-impact role managing the entire contract lifecycle—from initiation and drafting through negotiation, execution, and termination. You will oversee a team of direct reports and skip-level reports, providing guidance, feedback, and development opportunities in a fast-paced, high-growth environment.
Key responsibilities include revamping the contract review process with a focus on AI integration, performing high-volume contract review to ensure accuracy and compliance, managing vendor contracts including negotiation and dispute resolution, and collaborating with enterprise revenue teams to support sales and business development. You will design, build, and deploy AI tools and agents to automate contract intake, drafting, redlining, clause extraction, and risk flagging, partnering with engineering and legal operations to continuously tune models and guardrails.
Additionally, you will evaluate, select, and implement legal AI and contract lifecycle management (CLM) platforms, own vendor relationships and integrations, and extend AI adoption into other legal functions such as compliance, privacy, and litigation support. You will define and track efficiency and quality metrics (cycle time, accuracy, cost savings) to demonstrate ROI from AI initiatives and report progress to legal and business leadership.
The role requires a seasoned attorney with proven people management experience, strong collaboration and influence skills, and the ability to serve as a trusted advisor and business partner across the organization. You must maintain a systems-oriented, process-driven approach to contract management, identifying opportunities for efficiency and automation while working effectively under pressure with demanding stakeholders.
