Commercial Casualty Underwriting Leader (Director)

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. 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.

We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:

• Faster decisions

• Smarter, more accurate pricing

• Better risk outcomes

With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important industries and the progress they make possible.

Commercial insurance still runs on processes built decades ago. Underwriting is slow, and pricing leans on broad averages instead of the specifics of each risk. Technology can change how commercial risk is priced and managed, as long as it's paired with real underwriting expertise. The companies that get this right will shape the next era of the industry, and Shepherd intends to lead it.

Shepherd is a Managing General Underwriter (MGU) building the fastest and smartest AI-native commercial risk platform in the industry, where underwriters, data, and automation work together. The result is faster decisions for our broker partners and pricing that reflects the actual risk.

We started where the gap is widest: construction and energy, two of the most complex and highest-hazard segments in commercial insurance. Today we write Primary and Excess Casualty, Builder’s Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. Our mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation.

In 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 Capital, led our Series B round

• Costanoa Ventures, led our Series A round

• Spark Capital, led our Seed round

• Susa Ventures, lead our Pre-Seed round

• Y Combinator

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital. Intact also partners with Shepherd to provide capacity across its insurance products. Shepherd is also backed by leading institutional investors, including Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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.

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’ Compensation and Excess Casualty.

• Experience structuring both primary and excess casualty programs, including guaranteed-cost and loss-sensitive programs such as large deductibles and self-insured retentions.

• Sound judgment on contractual risk transfer, additional insured requirements, manuscript endorsements, and emerging exposures.

• Disciplined portfolio management, including limits, accumulation, and clash exposure.

• Established retail broker relationships at the regional and national level that can drive submission flow from day one.

• People leadership experience leading, mentoring, or managing underwriters, including setting authority and running underwriting audits.

• Executive presence to present strategy and results to leadership, capacity partners, and reinsurers.

• Comfort with ambiguity: you make sound decisions with incomplete information and adapt quickly as the business evolves.

• Willingness to travel about 25% to meet brokers, partners, and the team.

• A bachelor's degree or equivalent experience.

Shepherd's underwriting approach is client-centric with a heavy emphasis on an efficient process. Our goal is to leverage our technology and data to make quick, informed underwriting decisions tailored to our clients' specific needs.

In this role, you will:

• Define the strategy for retail commercial casualty, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth and loss-ratio targets.

• Support the development of underwriting guidelines, authority framework, referral rules, and rating approach.

• Partner with Product, Engineering, and Data to design the submission-to-bind workflow, pricing tools, and exposure and loss-trend views.

• Underwrite new and renewal primary and excess casualty within your authority.

• Own premium, profit, loss-ratio, retention, and expense results for the vertical.

• Use your retail broker relationships to drive submission flow in the first year, and serve as Shepherd's senior casualty voice with brokers, clients, and other stakeholders.

• Hire, coach, and grow a team of casualty underwriters and support staff as the book scales.

• Work with Corporate Underwriting to help set letters of authority, run underwriting audits, and coach from the results.

• Work with Claims, Actuarial, Customer Experience and Finance so the business is underwritten, serviced, and reported well.

This is a position based in our New York City, San Francisco, Chicago, Los Angeles, or Dallas–Fort Worth offices.

Shepherd runs on four values. Here's what each one means in this seat.

• 🚀 Think big, build big. We exist to protect progress and the industries that rely on it. You're building a casualty vertical meant to scale nationally, so the guidelines, team, and tools get designed for where the book is going, not just where it starts.

• 🤝 Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first leader of this vertical, you set the standard every casualty underwriter after you inherits.

• 🔄 Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best underwriting tools here come from underwriters who sit with engineers and data scientists, and much of this job is making that partnership work.

• 🔥 Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the appetite, the broker list, or the first submission. You build the plan, make the calls, and bind the first deal.

Shepherd runs on four values. Here's what each one means in this seat.

🐶 Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office