Senior Director - Litigation & Employment Counsel

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

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

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

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

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

About the Team

Handshake’s Legal team is a strategic and collaborative partner across the company, helping to build and deploy trusted products and services that advance our mission. We’re a lean but growing team that thrives on tackling complex issues at the intersection of frontier technology and the workforce—supporting every part of the business from product development and AI governance to commercial partnerships, data privacy, and employment. As the first dedicated counsel for Litigation and Employment, you’ll join a tight-knit group that values practical judgment, intellectual curiosity, bias for action, and a deep commitment to Handshake’s goal of democratizing access to opportunity.

Your Impact

Reporting to the General Counsel, you’ll define how Handshake manages dispute and employment risk and the intersection of frontier AI, the labor market and an evolving regulatory environment. You’ll build and lead Handshake’s Litigation and Employment function—setting the company’s approach to disputes and employment risk, shaping how Legal partners with Product, Engineering, and Operations, and growing the team and infrastructure required to support Handshake at scale.

Responsibilities:

• Litigation: Own the company’s litigation strategy and docket end-to-end across commercial, IP, employment, and platform/product disputes—directing pleadings, discovery, depositions, motion practice, mediation, arbitration, trial preparation, and settlement.

• Product and platform partnership: 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.

• Employment counseling: Serve as Handshake’s in-house employment expert— advising the People team and managers on day-to-day matters including hiring, performance management, separations, leaves of absence, reasonable accommodations, wage and hour, pay equity, internal investigations, a reductions in force across a multi-state workforce, plus a growing international footprint.

• Employment claims: Manage agency investigations, single-plaintiff and class/representative claims (including PAGA), severance and separation negotiations, and pre-litigation employee disputes; partner with the People team on root-cause learnings.

• Policies, training, and compliance programs: Partner with the People team to maintain and evolve the employee handbook, offer letters, restrictive covenants, separation templates, and required training programs (anti-harassment) anti-retaliation, manager training); monitor multi-state compliance obligations and lead rollout of new requirements (e.g. AI-in-hiring rules) across handbook, training, and product.

• Cross-functional leadership: 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.

You Have

• 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).

• 12+ years of combined law firm and in-house experience at a high-growth technology, gig platform, or marketplace company.

• Hands-on litigation experience managing complex commercial, employment, and/or platform-related disputes from intake through resolution, including first-chair trial, arbitration, and/or hearing experience.

• Deep in-house employment expertise across wage and hour, leaves and accommodations, investigations, and agency practice (EEOC, DFEH/CRD); strong expertise in worker classification laws and proven compliance strategies for gig and contractor populations at scale.

• Demonstrated ability to advise Product, Engineering, and Operations teams on legal questions arising from platform or marketplace products.

• Exceptional judgment and communication skills, with a passion for Handshake’s mission and the legal questions presented by the future of work.

Bonus Points

• Prior 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, user disputes, and trust & safety issues.

We Offer

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