Senior Product Manager, Platform (AI)

Vouch Insurance is a tech-enabled insurance advisory and brokerage focused on helping growing companies manage risk. They are seeking a Senior Product Manager to design an AI system that captures expert judgment and improves decision-making processes, while working closely with a team of AI and software engineers.

Responsibilities:

• Define what broker judgment looks like when it's captured correctly — the artifact schema that turns unstructured decisions into structured intelligence
• 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
• Own the broker relationship: understand what advice actually looks like, what experts trust, and what the system gets wrong in interesting ways
• Map workflows into tangible assets, advice units, and recommendations for brokers to act on
• Translate expert corrections into system improvements. When brokers tell you the output is wrong, that's your most valuable signal — make sure the team acts on it
• Own the evaluation framework: what does it mean for this system to be materially better than a generic AI model with the same context?
• Define success criteria for each phase — not in business metrics, but in system performance. Does the extraction work? Do brokers trust the patterns? Is month 8 better than month 5?
• 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
• Distinguish real learning from noise. Patterns that don't hold are not product failures — they're data. Own how the team uses them
• Translate domain complexity into a prioritization framework the team can execute against — without perfectly defined requirements
• Work with GTM and embedded domain experts to ensure the team is solving the right problem. You are the interface between what brokers need and what the system can produce
• Remove ambiguity without adding process. This team moves fast — your job is to create clarity, not overhead

Requirements:

• 3–5 years of product experience, including meaningful time in environments where the 'right' design wasn't obvious upfront — ideally 0-to-1 or early-stage product work
• Hands-on experience with deployed AI systems — not experimentation or exploration, but systems that shipped and operated in production. You understand where these systems are strong and where they fail
• Systems thinking: you design workflows, feedback loops, not feature sets. You've thought seriously about how systems learn and improve over time, not just how they process inputs. You connect the dots across systems and workflows
• Experience in regulated or complex professional domains — insurance, fintech, legal, healthcare, or similar fields where the signal is human judgment and the stakes of being wrong are real
• Comfort with ambiguity: you can define and make progress on a problem when the requirements are incomplete and success metrics don't yet exist
• Strong written and verbal communication — you can articulate technical tradeoffs to non-technical stakeholders and hold your own in architecture conversations with engineers
• An analytical mindset: you know how to distinguish signal from noise in both qualitative feedback and quantitative instrumentation
• Experience working with LLM-based systems — extraction pipelines, retrieval architectures, structured generation, or confidence calibration
• Background in knowledge management, expert systems, or any domain where the core challenge was capturing and systematizing human judgment
• Familiarity with data platforms (SQL, Snowflake) — you don't need to write the queries, but you should be able to read them
• Prior startup experience, or experience inside a company operating in a startup mode — where shipping, learning, and pivoting happened in weeks, not quarters