Senior Director of Litigation & Employment Counsel

• 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

Benefits

• Health Insurance: Comprehensive medical, dental, and vision coverage

• Fertility and family forming: Through a partnership, Handshake offers comprehensive family benefits, including infertility treatments and a $15K stipend, to its employees.

• LGBTQ+ coverage: All medical plans cover transgender services.

• Mental health: Discounts on a variety of wellness apps and an Employee Assistance Program with access to five free counseling sessions.

• Tax savings: Tax-advantaged benefits to save money on healthcare, dependent care, and other expenses.

• Life & disability insurance: Essential benefits and automatic coverage with basic life insurance, plus short-term and long-term disability coverage.

• 401k match: Dollar-for-dollar match up to 1% of pay, with a max of $1,200 per year.

• Equity: Our equity program includes grants at hire, refresher grants after two years of tenure, and grants alongside promotions.

• Financial management: Handshake partners to provide free professional financial planning services.

• Learning & development: Employees are provided with an annual stipend to use towards professional development, career development workshops, manager trainings, and 1-on-1 coaching through external partnerships

• Community leader support: Employee Resource Group leaders are compensated with a quarterly bonus for the high-impact work the role requires

• Parental leave: Leaves of 16 weeks for birth-giving parents and 10 weeks for non-birth-giving parents; the policy applies to adoptions as well. Handshake also partners to provide one-on-one coaching on preparing for leave and coming back from leave

• Flexible time off: No accrued time off or waiting period to take vacation. Two paid flexible holiday days off to observe holidays that closely align with religious, cultural, and personal needs

• Sabbatical: Paid six-week sabbatical to recharge and reset beginning at six years of continuous, full-time employment, and every four years thereafter

• Volunteer time off: Two days off for social and civil activism, volunteer work, and/or any related activities, including attending and participating in protests

• Hands-on litigation experience across commercial, employment, and platform disputes, including first-chair trial or arbitration experience

• Strong grounding in worker classification law and compliance strategy for gig and contractor populations at scale

• JD and active bar membership in at least one U.S. state (California admission or registration eligibility)

• Exceptional judgment and communication skills, with genuine interest in the legal questions shaping the future of work

• Deep employment law expertise: wage and hour, leaves and accommodations, investigations, agency practice (EEOC, DFEH/CRD)

• Track record advising Product, Engineering, and Operations on platform and marketplace legal questions

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

• 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