Principal, Technical Product Manager - AI Frontiers

Upwork•Palo Alto, CA

2d•$190,500 - $384,750•Remote

About The Position

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, from product and go-to-market motion to the operational program behind it. You'll set the strategy for moving a human-assisted experience toward an increasingly automated one, deciding which human steps AI absorbs first and how to steer that transition without sacrificing quality or customer trust. 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. 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.

Requirements

A track record of 0-to-1 product leadership, taking ambiguous, early-stage products from concept to real users and revenue, ideally more than once, with comfort operating when the spec is half-written.
AI-native product judgment grounded in agentic and LLM-driven systems, including human-in-the-loop design: knowing where AI embedded in a workflow wins, where bolt-on AI fails, and how to start with humans as the safety net and replace them as confidence grows.
Hands-on technical ability to prototype your own ideas and vibe-code working demos with AI coding tools, using build-alongside AI workflows to pressure-test concepts, align engineering, and move faster. You don't need to be a production engineer, but you're fluent enough with the technology to build with it, not just talk about it.
Strong technical partnership with engineering leaders on API boundaries, data modeling, and build-vs-buy trade-offs, alongside a service design and operations sensibility that treats the human-ops program as part of the product.
Executive-grade communication and a bias to ship, paired with the character to be direct in feedback, to be curious when plans change, and to be genuinely invested in the team's success.

Responsibilities

Own the product end-to-end, setting the vision and roadmap, writing and maintaining the spec, and making hard scope calls across a multi-stage, AI-assisted workflow to drive validated customer outcomes at scale.
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 a drop in 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.
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.
Present progress, learnings, and decisions to leadership, translating messy early-stage reality into crisp strategic recommendations.
Run the learning agenda by turning every workflow step into structured data, partnering with user research on moderated studies, and using both quantitative and qualitative signals to decide what to build, automate, or kill next.