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 a...