Senior Product Manager, Operator Experience - Handshake AI

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 Role

Handshake AI powers expert-labeled data collection at scale, matching domain experts with leading AI companies to train frontier models. We're hiring a Senior Product Manager, Operator Experience to ensure our Operations team can run complex data annotation projects independently—without needing engineering support for every new task type.

Operators are the backbone of HAI. They manage thousands of fellows, spin up new projects, maintain quality, and keep customers happy. Today, too much of that work requires custom tooling or EPD involvement. In this role, you'll change that—building self-serve systems that let operators see everything, respond immediately, and scale projects from 0 to 100k tasks/day with a click.

You'll be part of a tight-knit cross-functional team embedded with Operations, working alongside engineers and designers to ship tools that make our operators world-class. Your work will directly impact HAI's ability to scale revenue while maintaining the quality bar that differentiates us.

You'll own the lifecycle end-to-end for operator tooling, including:

• Product Strategy. Develop a cohesive product vision for operator independence that ladders up to HAI's broader goals. Define what "self-serve" means for operators and build the roadmap to get there.

• Product Development. Lead a high-performing cross-functional squad with engineering and design partners, from research and roadmap planning through delivery.

• Voice of the Operator. Live in the details of how operators work. Shadow their workflows, understand their pain points, and translate their needs into prioritized product investments.

• Goals, Metrics, and Tracking. Create clear success metrics (operator time-to-action, projects launched without EPD support, quality audit coverage) and drive accountability against them.

• Launch and Adoption. Partner with operations leaders to bring new tools to life. Run pilots to maximize learning, get close to users, and iterate quickly.

• Cross-HAI Partnership. Collaborate with Model Enablement and Fellow Experience squads—your work enables theirs. Operator independence requires mature platforms across the board.

Desired Capabilities

• 5+ years as a product manager partnering with engineering teams to ship code. Ideally in a many-stakeholder environment with dependencies and collaboration.

• Strong operational intuition. You've built tools for internal users, operations teams, or power users—not just consumer-facing features. You understand workflows, edge cases, and the difference between "works in demo" and "works at scale."

• Systems thinker. You can connect the dots across complex workflows, spot challenges and edge cases, and integrate multiple considerations into coherent product decisions.

• Data-informed but action-oriented. You use data to prioritize and measure, but you also trust user feedback and move quickly when the signal is clear.

• User-focused. You dive headfirst into understanding the needs of operators and build products grounded in observation and research.

Bonus Points

• Experience at a human data company or in operator/driver management

• Background in workflow or task management tools

• Experience building internal tools for operations teams at a high-growth company

• Familiarity with AI/ML data pipelines, annotation workflows, or quality assurance systems

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.