Subcontractor Default Underwriting Lead

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 to deliver faster decisions for broker partners and pricing that reflects actual risk. The company focuses on construction and energy — two of the most complex, highest‑hazard segments — writing Primary and Excess Casualty, Builder’s Risk, and Workers’ Compensation through a nationwide retail broker network. Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital, with participation from Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.

About the Role

Shepherd is launching a Subcontractor Default Insurance (SDI) product to support its Construction vertical. The Subcontractor Default Underwriting Lead will define the underwriting strategy, go‑to‑market approach, and drive long‑term profitable growth. This role is based in New York City, San Francisco, Chicago, Los Angeles, or Dallas–Fort Worth.

Responsibilities

• Define and build Shepherd’s SDI strategy: target contractor profiles, construction sectors, program sizes, limits and retentions, geographies, appetite, and growth and loss‑ratio targets.
• Establish underwriting guidelines, authority framework, referral rules, and rating approach for the product.
• Work with capacity partners to secure and structure program paper and keep 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 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; take action when risk changes.
• Own premium, profit, loss‑ratio, and retention results for the book.
• Leverage broker relationships to drive submission flow in year one; 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 — labor, materials, subcontractor financial stress — to keep Shepherd profitable and competitive.
• Collaborate with Risk Engineering, Actuarial, Corporate Underwriting, Claims, Customer Experience, and Finance to ensure the business is underwritten, serviced, and reported well.

Requirements

• 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 also considered).
• Deep knowledge of general contractors and construction managers across the construction industry.
• 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: reviewing contractor financial statements, work‑in‑progress (WIP) schedules, backlog, working capital, and bank lines; judging a contractor’s capacity to perform.
• Deep understanding of how general contractors prequalify, select, and manage subcontractors; ability to evaluate the strength of a contractor’s prequalification, monitoring, and default‑management practices.
• Technical command of SDI program structure: 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: making sound decisions with incomplete information and adapting quickly as the business evolves.
• Willingness to travel ~25% to meet brokers, partners, and the team.
• Bachelor’s degree or equivalent experience; background in construction accounting, finance, or law is a plus.

Compensation

Base salary range: $200,000 – $240,000, plus an annual performance bonus and equity in Shepherd. Offers within the range depend on experience and the relationships and market following you bring.

How We Work

• 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 guidelines, products, and tools are 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 come from underwriters who sit with engineers and data scientists.
• 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.

Benefits

• Premium Healthcare: 100% contribution to top‑tier health, dental, and vision
• Fertility Benefits & Family Building Support
• Unlimited PTO: flexibility to take time off, recharge, and perform
• Daily Lunches, Dinners & Snacks
• Offices in San Francisco, New York City, Dallas–Fort Worth, Chicago, and Los Angeles
• Professional Development: access to premium coaching, including leadership development
• Competitive 401(k) Plan
• Dog‑Friendly Office (SF office)