Senior Director - Litigation & Employment Counsel at Handshake — San Francisco, CA

About Handshake

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

About Handshake AI

About the Role

Handshake's Legal team is a strategic, collaborative partner across the company — spanning product development, AI governance, commercial partnerships, data privacy, and employment. As the first dedicated counsel for Litigation & Employment, you'll build and lead this function from the ground up, reporting to the General Counsel. You'll define how Handshake manages dispute and employment risk, partner with Product, Engineering, and Operations on the litigation- and employment-adjacent questions that surface in the platform itself — contractor and gig workflows, employer/recruiter features, user disputes, payout infrastructure, and platform terms.

• Serve as a senior thought partner to the leadership team on the disputes, employment, and platform-risk questions that shape company strategy—influencing how Handshake calibrates risk, expands into new products and markets, and navigates high-stakes inflection points, and building alignment with peer leaders in Product, Engineering, People, Finance, and Communications.
• Own the company's litigation strategy and docket end-to-end — commercial, IP, employment, and platform disputes — directing pleadings, discovery, depositions, motion practice, mediation, arbitration, and trial
• Partner cross-functionally with Product, Engineering, and Operations on the employment- and litigation-adjacent legal questions that surface in the platform itself—contractor and gig workflows on Handshake AI, employer/recruiter features on the careers platform, user disputes, payout infrastructure, content and trust & safety issues, and platform terms—providing practical, risk-calibrated guidance that helps teams ship.
• Serve as Handshake's in-house employment expert, advising the People team and managers on hiring, performance management, separations, leaves, accommodations, wage and hour, pay equity, and RIFs across a multi-state and growing international workforce
• Manage agency investigations, single-plaintiff and class/representative claims (including PAGA), and severance negotiations, partnering with the People team on root-cause learnings

You Have

• JD and active bar membership in at least one U.S. state (California admission or registration eligibility)
• 12+ years combined law firm and in-house experience at a high-growth tech, gig platform, or marketplace company
• Hands-on litigation experience across commercial, employment, and platform disputes, including first-chair trial or arbitration experience
• Deep employment law expertise: wage and hour, leaves and accommodations, investigations, agency practice (EEOC, DFEH/CRD)
• Strong grounding in worker classification law and compliance strategy for gig and contractor populations at scale
• Track record advising Product, Engineering, and Operations on platform and marketplace legal questions
• Exceptional judgment and communication skills, with genuine interest in the legal questions shaping the future of work

Bonus Points:

• Experience as the first or early litigation/employment hire at a high-growth company
• Familiarity with two-sided platform or marketplace businesses, including platform liability and trust & safety issues

We Offer