Senior Product Manager, Operator Experience - Handshake AI

Handshake•San Francisco, CA

About The Position

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:

Requirements

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.

Nice To Haves

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

Responsibilities

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.

Benefits

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

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