Upwork

Principal, Technical Product Manager - AI Frontiers

Palo Alto, California, United States · Principal · Contract

Sponsorship not specified$191k-$385kDetected 2 days ago

Machine LearningLLMsAgentic AIAccountingCustomer SupportLeadershipCommunicationMentoring

About the role

Upwork Inc.'s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled.
Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.
This is, first and foremost, a deeply technical role.

Drive the human-to-AI progression by deciding which human steps to automate first, instrumenting the system so each step is cleanly swappable for AI, and advancing automation on schedule without sacrificing quality or unit economics.
Coordinate a broad cross-functional surface across engineering (frontend, backend, ML, architecture), design, data, and platform partners (payments, security, legal and privacy, search, reliability), keeping a small, high-velocity core team unblocked.
Sharp judgment about where AI belongs and where it doesn't, including the ability to tell which problems genuinely need a model from those better solved with deterministic code, and an understanding of model failure modes deep enough to design around them rather than be surprised by them.
Fluency in human-in-the-loop design, knowing how to start with humans as the safety net and replace them as confidence grows, with a clear sense of which steps are safe to automate next and which aren't yet ready.
Hands-on technical ability to prototype your own ideas and vibe-code working demos with AI coding tools, paired with strong enough technical partnership to hold your own with engineering leaders on API boundaries, data modeling, and build-vs-buy tradeoffs.
Own go-to-market for early cohorts alongside sales and customer engagement, routing the right customers into the funnel, sharpening the value proposition, and protecting the business model as it scales.

Please note that a criminal background check may be required once a conditional job offer is made.

no committee approvals, no waterfall specs, and broad ownership backed by the infrastructure and runway of a public company.
Build an evaluation-first practice around the product, defining how you measure whether an AI step is good enough to ship, designing evals that catch failure modes like hallucination, drift, and silent degradation before customers do, and turning every workflow step into structured data that drives what gets built, automated, or killed next.
While we have a physical office in Palo Alto, we currently hire full-time employees in 34 U.S. states, making it easier than ever to join our mission from wherever you call home.
Our culture is built on trust, risk-taking, customer focus, and excellence, all in service of our core mission: to create economic opportunities so people have better lives.
Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce.

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This listing is sourced directly from Upwork's careers page and normalized into a canonical job model.