Executive Underwriter

What We DoShepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation.The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:Complex commercial construction projects routinely wait weeks for a single quoteLegacy carriers rely on static applications and disconnected systemsBrokers chase carriers through calls, emails, and resubmissionsWe built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:Faster decisionsSmarter, more accurate pricingBetter risk outcomes for insureds who invest in safer practicesWe're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.Our InvestorsIn March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:Intact Private CapitalSpark CapitalCostanoa VenturesY CombinatorSusa VenturesAnd several othersOur TeamWe're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.About YouWe are looking for a motivated and eager individual who’s passionate about the future of construction and eager to do the best work of their career.You would be a dream candidate if…You have a minimum of 7+ years of previous experience in the commercial underwriting space (Construction, Casualty, and/or Builder's Risk experience preferred)You aren’t afraid of ambiguityYou have a strong work ethic, are self-motivated, and have the ability to manage multiple tasks/projects simultaneouslyYou have exceptional interpersonal skills (verbal and written) and a high EQYou have strong sales and marketing skills and are able to position accounts and close dealsUnderwriting duties will include developing and negotiating price, coverage, terms and conditions for all new business and renewals while actively identifying target accounts that fit Shepherd’s underwriting appetiteBachelor’s degree or equivalent experienceAbout The RoleShepherd's underwriting approach will be client-centric with a heavy emphasis on an efficient process. Our goal will be to leverage our technology and data to make quick, informed, underwriting decisions tailored to our client's specific needs.Candidates must be able to demonstrate success in marketing, producer management, new business development, and the ability to successfully negotiate on all levels with both internal and external partners. Teamwork, communication, and negotiation skills are required. Solid background in risk analysis and experience with construction and/or casualty underwriting. Knowledge and proficiency with compliance, coverage, products and pricing strategies. Be adaptable and creative in a fast paced startup environmentThis is an onsite position in our New York City, San Francisco, or Dallas Fort Worth offices.Benefits🏥 Premium Healthcare100% contribution to top-tier health, dental, and vision🥕 Fertility benefits and family building support🏖️ Unlimited PTOFlexibility to take the time off, recharge, and perform🥗 Daily lunches, dinners, and snacksWe work together, and enjoy meals together too🖥️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices📚 Professional DevelopmentAccess to premium coaching, including leadership development🏦 Competitive 401(k) Plan🐶 Dog-friendly officePlenty of dogs to play with and make friends with in the SF officeCompensation Range: $185K - $228K