Careers

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 design direction for our P&C underwriting product, from discovery through iteration.
• Design agentic workflows and human-in-the-loop interactions with AI engineers.
• Tinker and build—use agentic coding tools like Claude Code to ship changes and experiment.
• Mentor designers and raise the design bar across your product area.
• Synthesize research into insights that shape roadmap and workflow design.

What We're Looking For

• 7+ years in product design with enterprise software shipped to production.
• AI fluency — you engage on agentic architectures, HITL patterns, and failure modes as a peer.
• Systems-first thinking — you map agent flows and handoff logic before opening Figma, and connect dots across projects.
• Strong facilitator — you can lead a room through a hard decision even when you don't have all the answers.
• Enterprise SaaS / Insurtech experience preferred — complex, data-driven workflows. Even better if you've worked in insurance.

You'll be a great fit if…

• You bring generalist range across the design process, from research to visual design to content.
• 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 and stay hands-on — trying new models and tools to learn what they make possible.

Additional Information:

• Expected full-time salary range between $165,000 to $190,000 + 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.

Our Commitment:

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.