Senior Director - Litigation & Employment 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 ABOUT HANDSHAKE AI 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. 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 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 http://joinhandshake.com/careers.