Senior Director - AI Commercial Counsel

About Handshake

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,…