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 be Handshake’s first dedicated Litigation and Employment lawyer—owning the litigation docket, advising the company on employment matters, and partnering with Product, Engineering, and Operations on the legal questions that arise from our human data and careers businesses.

Responsibilities:

• Litigation: Own the company’s litigation strategy and docket end-to-end—pre-litigation disputes, commercial cases, platform and product-related claims, IP matters, and employment disputes—managing outside counsel through pleadings, discovery, depositions, motion practice, mediation, arbitration, trial preparation, and settlement.

• Pre-litigation and disputes management: Triage demand letters, regulatory inquiries, and threatened claims; lead internal investigations; oversee litigation holds and e-discovery; and develop standardized intake and escalation processes as the company scales.

• 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, and reductions in force across a multi-state (and growing international) workforce.

• Worker classification: Lead worker classification analysis across Handshake’s businesses—including the Handshake AI expert network and other 1099 populations—balancing federal and state tests (including California’s ABC test and evolving multi-state standards), structuring engagement models, and partnering with Product, Operations and Finance on contractor onboarding, payouts, and offboarding.

• 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 operationalize updates as new laws take effect.

• 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 and tax infrastructure, content and trust & safety issues, and platform terms—providing practical, risk-calibrated guidance that helps teams ship.

• Outside counsel and budget: Build and manage a panel of litigation and employment firms, negotiate engagement terms and AFAs, and drive consistent outcomes.

• Cross-functional leadership: Brief executive leadership on material disputes, employment risk, and emerging exposure; partner with Communications on sensitive matters; and translate evolving legal standards into actionable guidance for internal teams.

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.

• Deep in-house employment expertise across worker classification, wage and hour, leaves and accommodations, investigations, and agency practice (EEOC, DFEH/CRD).

• 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

• First-chair trial, arbitration, or hearing experience.

• Experience with gig-economy or independent-contractor classification at scale, including multi-state and California-specific (ABC test, AB 5, PAGA) analysis.

• 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.

• Experience advising on AI- or data-platform products, particularly where worker classification, payouts, or labor regulations intersect with product design.

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

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.