Senior Director - Litigation & Employment Counsel

Handshake Technologies, Inc.

Job Overview

Location

San Francisco, CA

Job Type

Full-time

Full Job Description

📋 Description

• Serve as Handshake’s first dedicated Litigation and Employment Counsel, reporting directly to the General Counsel, and build the company’s litigation and employment function from the ground up.
• Own the end-to-end litigation strategy and docket across commercial, intellectual property, employment, and platform/product disputes, including pleadings, discovery, depositions, motion practice, mediation, arbitration, trial preparation, and settlement.
• Advise Product, Engineering, and Operations teams on legal risks arising from platform features such as contractor and gig workflows, employer/recruiter tools, user disputes, payout infrastructure, content moderation, and trust & safety issues.
• Act as the primary in-house employment expert, providing day-to-day guidance on hiring, performance management, separations, leaves of absence, reasonable accommodations, wage and hour compliance, pay equity, and internal investigations.
• Manage agency investigations and employment claims including single-plaintiff and class/representative actions (including PAGA), severance negotiations, and pre-litigation employee disputes, while partnering with the People team on root-cause analysis and systemic improvements.
• Partner with the People team to maintain, update, and roll out critical employment documents including the employee handbook, offer letters, restrictive covenants, separation templates, and mandatory training programs (anti-harassment, anti-retaliation, manager training).
• Monitor and ensure compliance with multi-state employment laws and lead implementation of new regulatory requirements such as AI-in-hiring rules across policies, training, and product workflows.
• Serve as a senior strategic advisor to the leadership team on employment, litigation, and platform-related risks that influence company strategy, product expansion, market entry, and high-stakes business decisions.
• Build and scale the legal infrastructure required to support Handshake’s rapid growth, including team development, external counsel management, and process automation for litigation and employment matters.
• Collaborate cross-functionally with Legal, People, Product, Engineering, Finance, and Communications to align on risk tolerance, compliance priorities, and operational workflows across a global workforce.
• Provide practical, risk-calibrated legal guidance that enables product teams to ship features while minimizing exposure to litigation and regulatory action in a fast-moving AI-driven labor market.
• Navigate complex legal questions at the intersection of frontier AI technology, gig economy labor models, and evolving employment regulations across multiple jurisdictions.
• Represent Handshake in negotiations with regulators, plaintiffs’ counsel, and external stakeholders on employment and litigation matters.
• Maintain up-to-date knowledge of emerging legal trends in AI, workforce classification, platform liability, and employment law to proactively advise the business.
• Foster a culture of legal pragmatism, intellectual curiosity, and bias for action within the Legal team and across the organization.

🎯 Requirements

• 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

🏖️ Benefits

• Equity in a fast-growing company
• 401(k) match, competitive compensation, financial coaching
• Paid parental leave, fertility benefits, parental coaching
• Medical, dental, and vision, mental health support, $500 wellness stipend
• $2,000 learning stipend, ongoing development
• Internet, commuting, and free lunch/gym in our SF office
• Flexible PTO, 15 holidays + 2 flex days
• Team outings & referral bonuses

Skills & Technologies

Senior

Remote

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

Handshake Technologies, Inc.

Visit Website

About Handshake Technologies, Inc.

Handshake Technologies provides a cloud-based career-services platform that connects university students, recent graduates, and employers. The software enables institutions to manage job postings, career fairs, on-campus interviews, and employer relations while giving students tools to discover internships and entry-level roles and giving employers access to early-career talent across a network of partner colleges and universities.

View Company Profile

Get more remote jobs like this

Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.

Weekly remote jobs and featured talent.

No spam. Only curated remote roles and product updates. You can unsubscribe anytime.