Underwriting Program Leader - Property and Casualty

PROGRAM LEADER - PROPERTY & CASUALTY

The company is on a mission to harness the power of data to revolutionize commercial insurance and enable a safer world. We're bringing much-needed innovation to the legacy, trillion-dollar commercial insurance industry with an AI-native platform that changes how an insurance company operates, from risk selection and pricing to underwriting, claims and loss prevention.

We proved the model in commercial auto, one of the toughest lines in insurance. Using real-time telematics data from more than 30 billion miles, we built predictive models that understand and price risk better. Since then we've grown to serve thousands of fleets and more than doubled written premium year over year, with a loss ratio, efficiency and customer experience that are redefining what's possible. Now we're taking the same platform (data, technology and underwriting discipline) into new lines of business and new programs.

With $270+ million raised, including our Series D round in December 2025, we’re only accelerating our growth, with strong support from top-tier VCs including Lightspeed, General Catalyst, and Valor. The company’s leadership team has previously helped scale multi-billion-dollar companies from scratch, including Samsara, Glassdoor, and Flexport, and includes industry veterans from Nationwide, The Hartford, and RLI.

About the Role

Are you a property and casualty underwriting leader with deep expertise in a profitable P&C niche, and a clear view of the program you’d build if you had the capital, capacity, and right platform behind you? We’re opening this role to P&C program leaders who want to build and own a program of their choice on the company’s platform. You bring the niche, the underwriting expertise and the relationships. We bring an AI-native platform, data science, engineering, capacity relationships, and the capital to launch and scale the program.

You’ll be accountable for the program’s P&L, top line and bottom line, and you’ll build it in close partnership with the company’s leadership. We’re not looking to replicate a traditional program. Together, we’ll design one that uses our data, technology and AI-native operating model from day one, and you’ll grow your own team as the program scales. The role comes with meaningful financial upside tied to the program’s success.

What you’ll do

• Bring a focused P&C market thesis and develop it into the program’s strategy, risk appetite, underwriting guidelines and operating rhythm in partnership with senior leadership, turning a focused market thesis into a disciplined, profitable program.

• Be the program’s lead line underwriter to get it off the ground, evaluating and pricing property and casualty risks and owning both new business and renewals.

• Own the brokerage relationships that drive the program’s growth: build the wholesale and retail distribution network, set production goals and be the face of the program in the market.

• Work closely with senior leadership, engineering, product and data science to shape the platform, underwriting workflows and operating procedures, so the program scales with technology instead of headcount.

• Own the relationship with reinsurers and capacity partners, and be accountable to them for portfolio performance (including catastrophe and accumulation exposure), reporting and renewals.

• Build and lead the program team (underwriting, distribution and operations) as the program grows.

About you

• 10+ years of underwriting in commercial property and casualty, with deep expertise in a defined niche.

• A track record of managing a large P&C portfolio, ideally $50M+ in premium, profitably and at scale.

• A clear program thesis. You can explain the P&C niche you’d target, why it’s profitable, why now, and how data and technology would give the program an edge.

• Proven underwriting discipline. You’ve written underwriting guidelines and appetite before, and your results show you stick to them.

• You’ve owned distribution. You’ve built and run broker relationships that drive production, and you enjoy getting on the road to meet partners.

• An entrepreneur at heart. You think like an owner, are comfortable with ambiguity, and use AI and technology to underwrite smarter and scale faster.

• You want to build something new, not repeat the old playbook. You’re excited to challenge traditional underwriting practices, work hand in hand with leadership and technologists, and do things the right way rather than the way they’ve always been done.

• Nice to have: experience launching a P&C program or new segment, working directly with reinsurers or capacity partners, or leading an underwriting team.

How to apply

In your application, include a short note on the P&C program you’d build: the class of business or niche, the opportunity you see, and the distribution relationships you’d bring.

Benefits

• Competitive salary and meaningful equity.

• Medical, dental and vision insurance.

• 401(k) with company match.

• Unlimited PTO.

• Work from home friendly.

We set our salary ranges using compensation data from companies similar to our stage and size. For this role, the estimated total compensation range for this position is $ 137,000 - 196,000. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job-related knowledge, transferable skills, work experience and our assessment of your level during the interview process. The company offers equity for all full-time employees, which is not included in the range listed above and will have an impact on your overall compensation.

The company offers a wide range of best-in-class, comprehensive benefits including 100% employer paid healthcare plans, an up to 4% 401k match program, paid time off, parental leave, wellness reimbursement, work-from-home stipend and more.the company is committed to building a diverse and inclusive workforce. If you’re interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. We'd like to consider you for this position and roles that may be a fit in the future.

The company is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, state, or local law. The company considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance.