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Vouch is a tech-enabled insurance advisory and brokerage serving ambitious companies in technology, life sciences, and professional services. Backed by over $200M in funding, Vouch combines deep industry expertise with AI-powered tools to deliver a better insurance experience. The company is the preferred insurance provider for customers of Y Combinator, Brex, Carta, and WeWork.
You will join a small, expert team building AI software for judgment-heavy insurance work—a system that learns from experts and improves measurably week over week. This is early-stage, production-ready work with real customers and real technical challenges. The role focuses on the hard problems at the intersection of making LLM systems durable, auditable, and measurably improving in a regulated domain.
Vouch values transparency, integrity, and empathy. The company operates with offices in San Francisco, Chicago, and New York City. This hybrid role requires in-office presence at least three days per week (Tuesday, Wednesday, Thursday) to foster collaboration and team building. You'll work on a genuinely interesting technical challenge where the company is betting on a specific approach to AI in insurance—not a commodity problem, but one with real edge and complexity.
