Principal, Technical Product Manager - AI Frontiers

Upwork•Palo Alto, CA

2d•Remote

About The Position

Upwork Inc.'s AI Frontiers operates like a funded startup inside Upwork, comprising a small, senior team focused on building the AI-native future of work. We are seeking a Principal Technical Product Manager to take ownership of a strategically critical 0-to-1 product initiative from conception through to its go-to-market strategy and operational execution. This role involves defining the strategy for transitioning a human-assisted experience to a more automated one, determining which human tasks AI can absorb and how to manage this transition without compromising quality or customer trust. The ultimate goal is to achieve high customer throughput, significantly faster time-to-value compared to current alternatives, and a reduction in human effort per engagement as automation is implemented. This is a hands-on role with broad ownership, free from committee approvals and waterfall specifications, supported by the infrastructure and resources of a public company.

Requirements

A proven track record of 0-to-1 product leadership, successfully guiding ambiguous, early-stage products from concept to market with real users and revenue, ideally multiple times.
Comfort operating in environments where the product specification is not fully defined.
AI-native product judgment, with expertise in agentic and LLM-driven systems, including human-in-the-loop design.
Understanding of where embedded AI in a workflow excels versus where bolt-on AI falls short.
Ability to initiate with humans as a safety net and progressively replace them as confidence in AI increases.
Hands-on technical capability to prototype ideas and create working demos using AI coding tools.
Experience using build-alongside AI workflows to test concepts, align with engineering, and accelerate progress.
Sufficient technical fluency to build with technology, not just discuss it.
Strong technical partnership skills with engineering leaders, focusing on API boundaries, data modeling, and build-vs-buy trade-offs.
A service design and operations sensibility that integrates the human-operations program as a core part of the product.
Executive-level communication skills.
A bias for shipping product.
The character to provide direct feedback, remain curious when plans change, and be genuinely invested in the team's success.

Responsibilities

Own the product end-to-end, including setting the vision and roadmap, writing and maintaining specifications, and making critical scope decisions for a multi-stage, AI-assisted workflow to achieve validated customer outcomes at scale.
Drive the progression from human-assisted to AI-driven processes by identifying which human steps to automate first, instrumenting the system for seamless AI integration, and advancing automation on schedule without impacting quality or unit economics.
Coordinate a wide range of cross-functional teams, including engineering (frontend, backend, ML, architecture), design, data, and platform partners (payments, security, legal and privacy, search, reliability), ensuring the core team remains unblocked.
Manage the operational program in collaboration with Operations, scaling the human expert function, supply, and playbooks that currently support the experience, while progressively decreasing human effort per engagement.
Oversee the go-to-market strategy for initial customer cohorts with sales and customer engagement teams, optimizing customer funnel routing, refining the value proposition, and safeguarding the business model as it scales.
Present progress, insights, and decisions to leadership, transforming early-stage complexities into clear strategic recommendations.
Manage the learning agenda by structuring workflow steps into data, partnering with user research for moderated studies, and utilizing both quantitative and qualitative data to inform decisions on what to build, automate, or discontinue.