Senior Director - AI Commercial Counsel

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We've grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

• Partner hand-in-hand with world-class AI labs, Fortune 500 partners and the world's top educational institutions

• Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders

• Build a massive, fast-growing business with billions in revenue

Human data is the core infrastructure to AI advancement. Frontier AI labs currently improve model capabilities with various data-intensive post-training techniques. We believe that data spend for AI training will increase by 3-5x in the next few years and continue for much longer as models take on new domains. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale.

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.

• 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

• A track record of structuring, negotiating, and closing complex, high-value commercial transactions with enterprise customers

• 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

• Executive presence and comfort with ambiguity, with the communication skills to earn trust with fast-moving internal teams and senior stakeholders

• Experience with AI data or training agreements, enterprise AI services, or transactions with frontier AI labs; AI experience is useful but not required

• Prior experience as the first or senior commercial lawyer for a high-growth business, including building scalable contracting processes

Handshake delivers benefits that help you feel supported and thrive at work and in life.

The below benefits are for full-time US employees.

🎯 Ownership: Equity in a fast-growing company

💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching

🍼 Family Support: Paid parental leave, fertility benefits, parental coaching

💝 Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

📚 Growth: $2,000 learning stipend, ongoing development

💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

🤝 Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.