Lead Product Designer

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.

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.

• Own the end-to-end design direction for our P&C 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.

• 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 coding to ship small changes, and experiment because you're genuinely curious.
• Strong facilitator: You lead productive conversations through ambiguity, align cross-functional teams on hard tradeoffs, and don't wait for someone else to call the meeting.
• Strong research craft: You can plan and run user research (from recruiting through synthesis) and translate findings into product decisions and shipped outcomes.
• Context switching with systems-level clarity: You can juggle a diverse set of projects, quickly build context, and connect the dots at a higher level so day-to-day decisions align with the broader product direction.
• Generalist range: Experience across the design process, from user research to visual design to content.
• Specialized depth in at least one: UX writing/content design, user research, visual design human-in-the-loop AI systems, or API design.
• Enterprise SaaS / Insurtech experience (preferred): Familiarity with designing for complex, data-driven workflows. Even better if you've worked in insurance before.

• You design the system before you design the screen—agent flows, confidence frameworks, and handoff logic come before pixels.
• You can lead a room through a hard decision even when you don't have all the answers.
• You're excited about building at the cutting edge of AI and discovering new UX patterns where best practices haven't been solidified.
• You want to rethink what a good design process looks like in the world of AI agents.
• You follow AI developments to understand how new capabilities can translate into better user experiences, and you stay hands-on by trying new models and tools to learn what they make possible.

• Expected full-time salary range between $165,000 to $180,000 + equity + benefits.
• Advertised and actual salary ranges may differ by geographic area, work experience, education, and/or skill level.
• About half the company works in the NYC office 3-4 days a week. This can be a remote role, but applicants need to work no more +/- 3 hours from Eastern time.
• This position does not include visa sponsorship. Candidates must be authorized to work in the United States without requiring employer sponsorship.

We foster an environment that welcomes professionals with a diversity of backgrounds and ideas. We value passionate professionals who bring creativity, determination, and a commitment to our mission. At Sixfold, every team member plays a crucial role, with opportunities to make meaningful and visible contributions to our success.

We believe in empowering our employees through continuous growth, learning, and a proactive problem-solving approach. Our comprehensive compensation package includes competitive salaries, equity opportunities, and robust benefits, all within a supportive and inclusive workplace culture. If you're driven to make a significant impact alongside exceptional colleagues, we want to hear from you.

We are committed to accessibility and provide reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout our recruitment process.If you have any difficulty using our online system and you need accommodation due to a disability, please reach out to us directly at (646) 847-8824.

Sixfold does not accept unsolicited agency resumes and is not responsible for any fees related to unsolicited resumes.