Commercial Casualty Underwriting Leader (Director) at Shepherd in San Francisco, CA

Job description

What we do Build the insurance behind the physical world. The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth. Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen. We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us. Real problems. Real ownership. Our engineers, designers, underwriters, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work. The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work around them. Join us to build systems whose decisions help real projects get built. 630+ customers / $500B+ insured project value Our investors Capital to build. Partners to grow with. $67M total funding / $42M Series B in March 2026 Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M. Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer. A bigger opportunity ahead We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible. Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both. Commercial Casualty Underwriting Leader (Director) Shepherd is launching a Retail Commercial Casualty vertical, as an expansion to its current Primary and Excess Casualty offerings.The Commercial Casualty Underwriting Leader will play a lead role in building and shaping new industry segments from the ground up. This is an opportunity to help define the underwriting strategy, go-to-market, and drive long-term profitable growth for a core pillar of Shepherd’s business. We're looking for someone with 10+ years of commercial property underwriting experience, a proven track record of leadership, deep relationships in the retail channel, and an entrepreneurial mindset who is excited to build something new with modern technology and a forward-thinking team. 🎯 About You You are a builder who wants to shape the future of commercial insurance and do the best work of your career. You have deep casualty expertise, a loyal broker network, and the drive to turn a blank page into a profitable book. You'd be a great fit if you have: • 10+ years of commercial casualty underwriting, with deep expertise in retail middle market and large accounts across classes such as real estate, retail, hospitality, manufacturing, and technology. • A proven record of profitable growth: originating new business, quoting, binding, and building a casualty book while managing to loss-ratio and combined-ratio targets. • Strong technical command of risk selection, exposure and loss analysis, loss development and trends, pricing, and coverage across Commercial General Liability, Commercial Auto, Workers’ Compe