Senior Product Manager, AI Pod

About Vouch:

Vouch is the insurance broker that powers ambition.

We’re a tech-enabled insurance advisory and brokerage purpose-built for growing companies in technology, life sciences, and professional services. Our clients are ambitious leaders building complex businesses, and we help them manage risk with tailored advice, smart coverage, and responsive service.

Backed by over $200M from world-class investors, Vouch combines deep industry expertise with AI-powered tools to deliver a better insurance experience. Our digital workflows reduce friction, speed up decisions, and give our clients the confidence to move faster.

Not only is this an exciting and growing team where you can drive a real impact on our operational scalability, but Vouch is also the preferred insurance provider to customers of Y Combinator, Brex, Carta, and WeWork. We’re a quickly growing startup that believes in transparency and acknowledgment with our team members and cultivating a values-driven company. Our values are "Be Client Obsessed", "Own it together", "Act with integrity and empathy", "Stay Curious and Grow", and "Empower People."

Vouch has employees located across the U.S., with offices in San Francisco, Chicago, and New York City. This role is aligned to our Chicago office. While this role has hybrid work flexibility, we require team members to be in the office at least three days per week (Tuesday, Wednesday and Thursday) to foster close collaboration and team building.

We're building an AI system that learns from how domain experts make decisions — and gets measurably better over time. The challenge isn't building another chatbot or copilot. It's designing a system that can extract structured intelligence from messy, real-world professional workflows, identify reliable patterns across many decisions, and surface that knowledge to the point where it's actually useful — without requiring anyone to change how they work.

You’ll be the founding partner on the pod embedded in a team of AI and software engineers. This isn't a conventional PM role. You're the person who owns the seam between humans and the system, runs a parallel build track so the pod isn't single-threaded on engineering, and holds us accountable to whether the engine is actually learning.

You’ll report to the Director of Product and interface regularly with the leadership team as the voice of the pod — communicating progress, surfacing blockers, and translating system performance into strategic implications.

• Sit alongside brokers. Watch them work. Try interaction patterns. Discover what "human in the loop" actually means in practice — not as a phrase, as a working interaction pattern.
• Ensure the team is solving the right problem. You are the interface between what brokers need and what the system can produce.
• Map workflows into tangible assets, advice units, and recommendations for brokers to act on.
• Design the feedback loops that allow domain experts to validate, correct, and enrich what the system surfaces — without adding friction to how they already work.
• Stand up solutions brokers can touch by mid-week. Without blocking on the Lead AI Engineer. You'll use Claude Code, Cursor, Lovable, v0, or whatever gets there fastest.
• Run the learning backlog. Track what we've learned about the engine, what we still don't know, and whether each iteration is closing the gap. This is interpretive work — reading instrumentation, forming hypotheses, feeding them into the next cycle.
• Build instrumentation with the engineering team to track whether the system's intelligence is actually improving. If it isn't, the answer is stop — and you should find that useful, not threatening.
• Author the metric system — north-star, driver, and guardrail metrics tied to unit economics (revenue per FTE, cost per case) — and hold the team accountable to it.
• Recruit and run the pilot. Pick the first users yourself, sell them on it, walk each one through the system 1:1, and convert their feedback into the next build cycle. Adoption is yours to earn, not GTM's to deliver.

• You’v…