Principal, Technical Product Manager

About the role

Join the AI Frontiers team, an internal startup within Upwork focused on building the future of AI-native work. You will lead a high-priority, 0-to-1 product initiative, managing the technical strategy and execution required to automate complex human-assisted workflows.

Key facts

What you'll do

• Direct the product vision, roadmap, and specifications for a multi-stage AI-assisted workflow.
• Determine the appropriate technical architecture for each workflow step, choosing between deterministic logic, retrieval, fine-tuning, or agentic orchestration.
• Manage the transition from human-led processes to automated systems while maintaining strict quality and unit economic standards.
• Build an evaluation framework to identify failure modes such as hallucination or system drift before they impact users.
• Lead cross-functional collaboration across engineering, ML, design, data, and platform teams to keep development moving quickly.
• Oversee operational programs to scale human expert functions while reducing manual effort per engagement.
• Execute go-to-market strategies, refining value propositions and business models for early customer cohorts.

Requirements

• Proven track record of 0-to-1 product leadership, taking ambiguous concepts to market and revenue.
• Deep technical understanding of modern AI, including LLMs, agentic systems, retrieval, and cost/latency tradeoffs.
• Ability to engage as a peer with ML engineers regarding API boundaries, data modeling, and build-versus-buy decisions.
• Experience with human-in-the-loop design and the ability to define safe, incremental automation paths.
• Hands-on prototyping skills using AI coding tools to demonstrate concepts.
• Executive communication skills and a bias for shipping functional products.

Skills & tools

• LLMs and Agentic Orchestration
• Retrieval Augmented Generation (RAG)
• Fine-tuning and Model Evaluation
• Deterministic Logic vs. Probabilistic Modeling
• Data Modeling and API Architecture
• Human-in-the-loop Workflow Design

Practical notes

• Benefits include comprehensive medical coverage, unlimited PTO, 401(k) matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan.
• Interviews are recorded via BrightHire for transcription purposes; candidates may opt out during scheduling.
• A criminal background check may be required post-offer, conducted in accordance with the California Fair Chance Act.