Backed by Y Combinator.
About the role
You'll inherit a strong product and a capable team, but that's the starting point, not the job. The job is figuring out what underwriting becomes once AI stops assisting and starts deciding, and getting there faster than the market expects. You prototype to find out, not to perform speed. You're drawn to this problem because the underwriter of the future is one of the more interesting design problems in software right now.
What they're looking for
- You think about the underwriter of the future the way some people think about a chess position. You can't stop turning it over, and you have hot takes about what's underrated
- You said you built something yourself, you mean you wrote the prompt chains, ran the eval, sat with the customer, not that you wrote the spec and someone else built it
- You took from zero to production, and you know the ARR, retention, or adoption number it moved
- Facing a new problem, your instinct is to build something small and get it in front of a real customer rather than write a spec. You find the lighthouse customer, get honest feedback, and iterate from there
- You've inherited good teams before and know the difference between "this is broken, replace it" and "this is good, but it has to improve." You default to the latter until proven otherwise
More about this role
Insurance underwriting runs on human judgment, manual workflows, and knowledge locked in someone's head. It breaks when that person leaves and doesn't scale when the book doubles. Sixfold is building AI agents that understand risk the way a 20-year veteran underwriter does. Not summaries or flags, but systems that make real decisions on billions in premium for some of the world's largest carriers. AI is the product, the workflow, and the moat. If you think in systems, move fluidly from research to pixels, and are energized by designing AI-native experiences where the best practices haven't been written yet — this role was made for you.
🏔 Product: Sixfold is the AI brain for underwriting. Our platform handles submissions at scale, assessing risk against appetite, surfacing cited insights, and deploying AI agents to handle research, referrals, and triage so underwriters can focus on building profitable portfolios.
💪 Team: A focused team of insurance operators, AI researchers, and engineers who love hard problems. We've pushed the boundaries of what AI can do with unstructured data — from teaching AI to understand that a bakery in Florida faces different risks than one in Montana, to...
Browse similar: Startup jobs