Senior Director (AI Commercial Counsel)

• Handshake’s Legal team is a strategic partner to the business, helping Handshake move quickly, make sound decisions, and build trusted products and services
• We’re a lean, collaborative team solving novel questions at the intersection of frontier technology and the workforce
• As the senior commercial lawyer dedicated to Handshake AI and Handshake AI Enterprise, you’ll help turn ambitious opportunities into durable commercial relationships with leading AI labs and enterprise customers
• You’ll join a team that values commercial judgment, intellectual curiosity, urgency, and a deep commitment to Handshake’s mission of democratizing access to opportunity
• Reporting to the General Counsel, you’ll define and lead the commercial legal strategy for Handshake AI and Handshake AI Enterprise, with a focus on our most strategic frontier lab and enterprise customers
• You’ll serve as lead lawyer, strategic advisor, and deal quarterback on high-value, bespoke transactions
• Strategic commercial transactions: Own the legal strategy and negotiation of Handshake AI’s most important customer and partner transactions, including AI data and training agreements, enterprise AI services, and strategic partnerships
• Bespoke deal structuring: Create novel commercial structures for complex opportunities where market standards are still developing—translating product, operational, and economic objectives into durable agreements and clear allocations of risk
• Data, IP, privacy, and security: Lead negotiations and provide practical advice on data rights, model-training and output rights, IP ownership and licensing, privacy, and security, with a deep understanding of how those terms affect Handshake’s products and delivery model
• Customer and executive engagement: Represent Handshake directly with sophisticated customer legal teams and senior stakeholders, lead high-stakes negotiations, brief executives on material issues, and drive decisions that keep strategic deals moving
• Cross-functional partnership: Partner closely with Sales, Partnerships, Product, and Operations throughout the deal lifecycle—from opportunity shaping and term-sheet strategy through negotiation, signature, implementation, renewal, and expansion
• Commercial function leadership: Build the templates, playbooks, approval frameworks, deal-desk practices, and contracting workflows needed to improve deal velocity and risk calibration; establish the commercial legal function and build the team as the business grows

Benefits

• Health Insurance: Comprehensive medical , dental, and vision coverage
• Fertility and family forming: Through a partnership, Handshake offers comprehensive family benefits, including infertility treatments and a $15K stipend, to its employees.
• LGTBQ+ coverage: All medical plans cover transgender services.
• Mental health: Discounts on a variety of wellness apps and an Employee Assistance Program with access to five free counseling sessions.
• Tax savings: Tax-advantaged benefits to save money on healthcare, dependent care, and other expenses.
• Life & disability insurance: Essential benefits and automatic coverage with basic life insurance, plus short-term and long-term disability coverage.
• 401k match: Dollar-for-dollar match up to 1% of pay, with a max of $1,200 per year.
• Equity: Our equity program includes grants at hire, refresher grants after two years of tenure, and grants alongside promotions.
• Financial management: Handshake partners to provide free professional financial planning services.
• Learning & development: Employees are provided with an annual stipend to use towards professional development, career development workshops, manager trainings, and 1-on-1 coaching through external partnerships
• Community leader support: Employee Resource Group leaders are compensated with a quarterly bonus for the high-impact work the role requires
• Parental leave: Leaves of 16 weeks for birth-giving parents and 10 weeks for non-birth-giving parents; the policy applies to adoptions as well. Handshake also partners to provide one-on-one coaching on preparing for leave and coming back from leave
• Flexible time off: No accrued time off or waiting period to take vacation. Two paid flexible holiday days off to observe holidays that closely align with religious, cultural, and personal needs
• Sabbatical: Paid six-week sabbatical to recharge and reset beginning at six years of continuous, full-time employment, and every four years thereafter
• Volunteer time off: Two days off for social and civil activism, volunteer work, and/or any related activities, including attending and participating in protests

• JD and active membership in good standing in at least one U.S. state bar (California admission or eligibility to register as in-house counsel in California)
• 10+ years of combined legal experience, including law firm training and in-house experience at a sophisticated technology company
• Deep experience with enterprise technology and data licensing, including data-use rights, IP, privacy, and security terms
• Exceptional commercial instinct and judgment, with the ability to identify what matters and calibrate risk to business objectives
• A track record of structuring, negotiating, and closing complex, high-value commercial transactions with enterprise customers
• Executive presence and comfort with ambiguity, with the communication skills to earn trust with fast-moving internal teams and senior stakeholders
• Prior experience as the first or senior commercial lawyer for a high-growth business, including building scalable contracting processes
• Experience with AI data or training agreements, enterprise AI services, or transactions with frontier AI labs; AI experience is useful but not required