Subcontractor Default Underwriting Lead

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 Subcontractor Default Insurance (SDI) product in support of its existing Construction vertical. The Subcontractor Default Underwriting Lead will play a lead role in building and shaping the new SDI product expansion, and define how we best evaluate subcontractor prequalification controls and subcontractor management practices. This is an opportunity to help define the underwriting strategy, go-to-market, and drive long-term profitable growth for the core pillars of Shepherd’s business. We're looking for someone with 8+ years of SDI underwriting experience, a proven track record of leadership, deep broker relationships, 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 subcontractor default insurance 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:

• 8+ years of underwriting experience, with significant direct experience underwriting Subcontractor Default Insurance at an established SDI carrier or program. Contract surety underwriters with meaningful SDI exposure will also be considered.

• Deep knowledge of general contractors and construction managers across the construction industry.

• A proven record of building and growing an SDI portfolio profitably: originating new business, quoting, binding, and scaling premium while managing to loss-ratio and combined-ratio targets.

• Strong financial analysis skills, including reviewing contractor financial statements, work-in-progress (WIP) schedules, backlog, working capital, and bank lines, and judging a contractor's capacity to perform.

• Deep understanding of how general contractors prequalify, select, and manage subcontractors, and the ability to evaluate the strength of a contractor's prequalification, monitoring, and default-management practices.

• Technical command of SDI program structure, including enrollment, per-loss deductibles, co-pays, per-loss and aggregate limits, project and annual programs, and how SDI compares to subcontractor bonds.

• Sound judgment on policy wording, direct and indirect cost coverage, and default, cure, and completion scenarios, working closely with claims on complex losses.

• Established 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. A background in construction accounting, finance, or law is a plus.

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 and build Shepherd’s SDI strategy,including target contractor profiles, construction sectors, program sizes, limits and retentions, geographies, appetite, and growth and loss-ratio targets.

• Help establish the underwriting guidelines, authority framework, referral rules, and rating approach for the product.

• Work with capacity partners to secure and structure the paper behind the program, and keep those partners informed on results.

• Partner with Product, Engineering, and Data to design the submission-to-bind workflow, contractor financial and prequalification analysis tools, and portfolio views.

• Underwrite new and renewal SDI programs within your authority, including financial review, prequalification audits, and meetings with contractor leadership.

• Set up procedures for monitoring in-force programs for changes in contractor financial health, backlog, and subcontractor enrollment, and take action when the risk changes.

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

• Use your broker relationships to drive submission flow in the first year, and actively market Shepherd's SDI product at broker and client meetings, industry events, and through targeted business development.

• Hire, coach, and grow a team of SDI underwriters as the book scales.

• Track construction market trends, including labor, materials, and subcontractor financial stress, to keep Shepherd profitable and competitive.

• Work with Risk Engineering, Actuarial, Corporate Underwriting, Claims, 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 an SDI vertical meant to scale nationally, so the guidelines, products, 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 underwriter in this vertical, you set the standard every SDI 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