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

The Role

We’re looking for a VP, Operations to drive excellence and scalability across our core operations. This leader will oversee a portfolio of central operations teams — including Fellow Experience, Pay, Data & Analytics, and Training & Learning — that support the teams of operators powering our Human Data delivery engine, as well as a Strategy team helping to chart the future of the business.

The ideal candidate is an operator–strategist hybrid: analytical, execution-minded, and capable of building scalable systems and teams that keep pace with rapid company growth. This role sits at the intersection of business operations, people strategy, and execution enablement.

What You’ll Do

• Lead and Scale Core Operations: Evolve central teams responsible for Fellow Experience, Pay Operations, Data Analytics, Strategy, and Training & Learning to drive excellence in our operations

• Drive Operational Strategy: Translate company goals into operational plans that improve efficiency, quality, and Fellow engagement.

• Manage Cross-Functional Alignment: Partner with Product, Growth, Ops Delivery, and People teams to ensure smooth execution of initiatives

• Operational Analytics & Planning: Build dashboards, metrics, and business reviews that measure performance and inform strategy.

• Org Design & Capacity Planning: Ensure that operational structures scale efficiently as the business grows.

• Executive Leadership: Serve as a strategic advisor to the CEO and broader leadership team on operational scaling, resource allocation, and growth readiness.

What You Bring

• 10-15+ years of experience in operations, strategy, or business leadership, ideally in tech, AI, or platform-based companies.

• Proven track record building and managing high-performing, multidisciplinary teams.

• Comfort operating in ambiguous, fast-scaling environments.

• Strong analytical and structured problem-solving skills.

• Experience using systems thinking to design processes at scale.

• Excellent communication and executive presence; able to translate between operational and executive audiences.

Nice to Have

• Experience leading workforce operations or marketplaces (e.g., gig or flexible workforce models).

• Prior experience in management consulting, biz ops, or strategy roles in growth-stage tech.

• Familiarity with AI/ML operations or data annotation environments.

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.