$245K – $285K/yr
VP, Product 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. Who We Are 🏔 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 knowing when a manufacturing company's pivot from toys to medical devices fundamentally changes their risk profile. We ship fast and stay close to customers. 📈 Traction: Processing billions in premium for some of the world's largest carriers. We know AI. We know underwriting. We're building what comes next. 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. In this role, you will: