Lead Product Designer

Who we are At Sixfold, we’re building the AI platform that transforms how insurers evaluate and price risk. Not just another tool that generates summaries or flags issues—we’re creating AI agents that actually understand risk the way veteran underwriters do. Our platform is processing billions in premium for some of the world’s largest carriers, and we’re just getting started. The technical challenges are wild. We’re teaching AI to understand that a bakery in Florida faces different risks than one in Montana. To know when a manufacturing company’s pivot from toys to medical devices fundamentally changes their risk profile. To make million-dollar decisions with the same intuition as someone who’s been underwriting for 20 years. What makes Sixfold special isn’t just the technology—it’s that we’re building it with people who deeply understand insurance. Our team includes folks who’ve built and scaled carriers, researchers who’ve pushed the boundaries of AI, and engineers who just love solving seemingly impossible problems. We’re still early, but the impact is already real. If you want to build AI that matters—that affects real businesses, real people, and billions in economic activity—Sixfold is where you should be. We’re not just digitizing insurance. We’re reimagining what it can be. The Role We’re looking for a Lead Product Designer to own design for our flagship Property Casualty underwriting AI product. This role is ideal for a senior, generalist designer who thrives in a highly collaborative environment and enjoys tackling complex problems in enterprise AI software. You’ll partner with PMs, developers, and AI engineers as a peer—shaping an experience that blends agent automation with the nuanced judgment of underwriters, and defining how our agents reason, act, fail, and hand off to humans. This role reports to our Head of Design and is a senior IC position with mentorship responsibilities, with meaningful influence on our design patterns, process, and culture. What You'll Do Own the end-to-end design direction for our PC underwriting product—from discovery through implementation and iteration. Drive product strategy alongside PMs by framing problems, running discovery, and bringing back recommendations that shape the roadmap. Design agentic workflows and human-in-the-loop interactions—defining how AI agents plan, execute, fail, and hand off to underwriters. Engage directly with AI engineers on how agent behavior maps to user intent. Use agentic coding tools like claude codea to push quick design changes and refinements directly to the product. Lead alignment conversations and facilitate through ambiguity—even when you're not the subject matter expert in the room. Mentor designers on the team and raise the design bar across your product area. Jam with the design team on new designs, the design system, agentic prototyping, and anything else that enables Sixfold designers to excel. Drive continuous discovery with underwriters and customer teams—running interviews, concept tests, and usability studies to pressure-test direction. Synthesize research into crisp insights and recommendations that shape roadmap, agent behavior, and workflow design. Help our customers smoothly transition to the world of enterprise AI agents. What We're Looking For 7+ years of experience as a product designer with a proven track record in enterprise software. A portfolio demonstrating outcomes fully delivered into production. AI fluency: You can engage with engineers on agentic architectures, HITL patterns, and failure modes as a peer—not just as someone who designs the UI layer on top. You understand how agents reason and where humans need to intervene. Systems-first thinking: You design the logic before the screen. You map agent flows, confidence thresholds, and handoff moments before opening Figma. Tinkerer mentality: When you see an inefficiency, you build something to fix it. You prototype with AI tools, use agentic co ... (truncated, view full listing at source)