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Director, Commercial Law

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Logo of HopSkipDrive

HopSkipDrive

51 - 200 employees

Founded 2014

📦 Logistics

💼 Consulting

✈️ Travel

💰 $37M Series D on 2022-09

Logistics • Consulting • Travel

HopSkipDrive is a leading provider of innovative and scalable school transportation solutions, partnering with schools, districts, and counties to provide safe, reliable transportation for youth. They specialize in providing alternatives to traditional school bus routes, catering to students' non-routine needs, those in foster care, and students with special transportation requirements. HopSkipDrive also supports personalized and small group transportation solutions, and uses RouteWise AI technology for transportation optimization. Their service is known for being 40% more affordable than traditional underutilized bus routes. They also address challenges such as bus driver shortages and provide a flexible network of CareDrivers, ensuring safety and reliability.

📋 Description

• Revamp and revitalize the contract review process with a focus on AI-driven efficiency • Oversee the entire contract lifecycle from initiation and drafting through negotiation, execution, and termination • Perform high-volume contract review for accuracy, completeness, policy compliance, and legal compliance • Manage vendor contracts, including negotiating terms, monitoring performance, and resolving disputes • Lead and scale teams in a fast-paced, high-growth environment • Manage direct and skip-level reports, providing guidance, feedback, and development opportunities • Collaborate with enterprise revenue teams on sales and business development efforts • Balance competing priorities and meet tight deadlines with demanding stakeholders • Maintain a systems-oriented, process-driven approach to contract management • Design, build, and deploy AI tools or agents for contract intake, drafting, redlining, clause extraction, and risk flagging • Partner with engineering and legal operations to tune models, playbooks, and guardrails • Evaluate, select, and implement legal AI and CLM platforms while managing vendors, integrations, and performance metrics • Extend AI adoption into compliance, privacy, and litigation support/eDiscovery • Define and track efficiency and quality metrics, including cycle time, accuracy, and cost savings • Report AI initiative progress to legal and business leadership

🎯 Requirements

• 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 of experience drafting, reviewing, and negotiating commercial contracts, including vendor agreements, service contracts, NDAs, and licensing agreements • Hands-on experience implementing or configuring AI/GenAI tools for legal work • Experience building or tuning AI agents for contract review, drafting, or negotiation • Experience with prompt engineering and evaluating model outputs for accuracy and risk • Experience evaluating and implementing legal AI or contract lifecycle management (CLM) platforms, including vendor management and system integrations • Working knowledge of AI governance and regulatory considerations, including the EU AI Act, state-level AI laws, and data privacy requirements • Track record of people management and mentoring direct reports • Strong communication and legal skills for counseling internal stakeholders • Familiarity working with company partners to close high-value deals and launch products • Ability to manage commercial contracting processes, support product development, manage privacy law, and align business strategies with legal requirements • Ability to lead projects and design processes that automate and streamline high-velocity work • Solutions-oriented mindset • Must be licensed to practice law and maintain bar membership in good standing

🏖️ Benefits

• Equity stock options for every full-time employee • Flexible vacation • Medical insurance • Dental insurance • Vision insurance • Life insurance • 401(k) • FSA • Opportunity to work for a VC-backed company with significant upside potential

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