Principal, Technical Product Manager - AI Frontiers

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. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. 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.

AI Frontiers operates like a funded startup inside Upwork: a small, senior team with a real product in market and a clear mandate to build the AI-native future of work. We're hiring a Principal Technical Product Manager to own one of our most strategically important 0-to-1 bets end-to-end.

This is, first and foremost, a deeply technical role. You'll set the strategy for moving a human-assisted experience toward an increasingly automated one, and the hardest calls in that transition are technical ones: which parts of the workflow genuinely benefit from a model, which are better served by deterministic systems, and how to sequence automation so quality and trust never regress.

Success in this role means customers moving through the experience end-to-end at a high rate, achieving meaningfully faster time-to-value than today's alternatives, and human effort per engagement trending down as automation lands, all without a drop in quality. This is a builder's role: no committee approvals, no waterfall specs, and broad ownership backed by the infrastructure and runway of a public company.

Responsibilities:

• Own the product end-to-end: set the vision and roadmap, write and maintain the spec, make hard scope calls across a multi-stage, AI-assisted workflow, and translate messy early-stage reality into crisp strategic recommendations for leadership.
• Make the core AI architecture calls, deliberately choosing among retrieval, prompting, fine-tuning, agentic orchestration, and plain deterministic logic based on what each step of the problem actually requires, rather than defaulting to a model simply because one is available.
• 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.
• 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.
• 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.
• Run the operational program in partnership with Operations, scaling the human expert function, supply, and playbooks that power the experience today while steadily reducing human effort per engagement.
• 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.

What It Takes to Catch Our Eye:

• A deep, first-principles understanding of modern AI, including how LLMs and agentic systems actually work under the hood (context and retrieval, tool use, fine-tuning, evaluation, and the real latency, cost, and reliability tradeoffs involved), with the fluency to hold a technical conversation with ML engineers as a peer.
• 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.
• A clear-eyed view of why bolt-on AI so often fails while embedded, well-scoped AI works, informed by real product experience rather than industry hype.
• A track record of 0-to-1 product leadership, having taken at least one ambiguous, early-stage product from concept to real users and revenue, ideally more than once, with comfort operating when the spec is half-written.
• 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.
• Executive-grade communication and a bias to ship, paired with the character to give direct feedback, be curious when plans change, and be genuinely invested in the team's success.

Come change how the world works.

At Upwork, you'll shape the future of work for a global, remote-first workforce, creating economic opportunities for professionals worldwide. 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. We embrace authenticity and inclusion, encouraging everyone to bring their whole selves to work. Personal and professional growth is a priority here, supported through development programs, mentorship, and our Upwork Belonging Communities.

We're proud to offer benefits that go beyond the basics, including comprehensive medical coverage for you and your family, unlimited PTO, a 401(k) plan with matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan. Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.

Ready to help shape the future of work? Check out our Careers page and follow us on LinkedIn, Facebook, Instagram, TikTok, and X to learn more about life at Upwork.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances. The Company is committed to conducting an individualized assessment and giving all individuals a fair opportunity to provide relevant information or context before making any final employment decision.

We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled.

To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice.