Director, Commercial Law

HopSkipDrive
Arizona, California, Colorado, District of Columbia, Florida, Georgia, Illinois, Indiana, Kansas, Massachusetts, Maryland, Michigan, Minnesota, Missouri, North Carolina, New Jersey, New Mexico, Nevada, New York, Oklahoma, Oregon, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, Wisconsin
Workplace: RemoteFull timeUSD 189,000 - 200,000 annuallyFunction: Executive & General ManagementExperience: 10+ yearsEducation: professionalSkills: ["People management","Collaboration","Communication","Legal risk advising","Solutions-oriented mindset"]

Revamp and lead the end-to-end commercial contract lifecycle, from drafting and negotiation through execution and termination, including high-volume contract review. Manage vendor contracts and disputes while scaling people leadership across direct and skip-level reports. Partner with enterprise revenue teams and build AI-driven contract intake, drafting, redlining, clause extraction, and risk flagging—evaluating CLM/AI tools, integrating systems, and tracking cycle-time and quality/ROI metrics.

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HopSkipDrive
HopSkipDrive
2 days ago

Director, Commercial Law

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Last checked: 10 hours agoStatus: Live

Job Summary

Revamp and lead the end-to-end commercial contract lifecycle, from drafting and negotiation through execution and termination, including high-volume contract review. Manage vendor contracts and disputes while scaling people leadership across direct and skip-level reports. Partner with enterprise revenue teams and build AI-driven contract intake, drafting, redlining, clause extraction, and risk flagging—evaluating CLM/AI tools, integrating systems, and tracking cycle-time and quality/ROI metrics.
Location: Arizona, California, Colorado, District of Columbia, Florida, Georgia, Illinois, Indiana, Kansas, Massachusetts, Maryland, Michigan, Minnesota, Missouri, North Carolina, New Jersey, New Mexico, Nevada, New York, Oklahoma, Oregon, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, Wisconsin
Workplace: Remote
Employment Type: Full time
Job Function: Executive & General Management
Seniority: Director level

Key Responsibilities

  • •Revamp and scale the contract review process for efficiency, with a focus on AI use.
  • •Oversee the entire commercial contract lifecycle from initiation and drafting through negotiation, execution, and termination.
  • •Manage vendor contracts by negotiating terms, monitoring performance, and resolving disputes.
  • •Lead and scale people management across direct reports and skip-level reports in a fast-paced, high-growth environment.
  • •Design, build, deploy, and operationalize AI tools/agents and evaluate/implement legal AI/CLM platforms, integrating systems and tracking efficiency/quality metrics to demonstrate ROI.

Pay and Benefits

Salary: USD 189,000 - 200,000 annually
Equity and Bonus:Equity
Perks:Health InsuranceDentalVisionLife Insurance401kFsaEquityPaid Leave

Key Requirements

  • •Juris Doctor (JD) from an accredited law school and active Bar Membership in good standing to practice law.
  • •10+ years of experience working in-house or at a law firm, with 10+ years drafting, reviewing, and negotiating commercial contracts (e.g., vendor agreements, NDAs, service and licensing agreements).
  • •Hands-on experience implementing/tuning AI or GenAI tools for legal work (e.g., building/tuning AI agents, prompt engineering, evaluating outputs for accuracy and risk).
  • •Experience evaluating and implementing legal AI or contract lifecycle management (CLM) platforms, including vendor management and system integrations.
  • •A track record of people-management, mentoring direct reports, and advising stakeholders on contractual risks, obligations, and liabilities.
Experience:10+ yearsIn-house legalLaw firmLegal techAI/GenAIContract lifecycle management (CLM)
Education:Professional (JD, MD, etc.)
Skills:People managementCollaborationCommunicationLegal risk advisingSolutions-oriented mindset
Licenses:Bar Membership
Languages:English
Tech Stack:AIGenAIAI agentsPrompt engineeringContract lifecycle management (CLM)IroncladIvoHarveySpellbookLegoraEU AI ActEDiscovery

Company Brief

HopSkipDrive
Provides on-demand, vetted-driver transportation services for children and seniors, partnering with school districts, families, and care providers to offer safe, scheduled, and ad hoc rides through a tech-enabled platform.
Industry: Mobility Platforms
Company Size: Large (251 to 1,000 employees)
Growth: Scaleup
Funding: Series D
Headquarters: Los Angeles, United States
Founded: 2013
WebsiteLinkedIn