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Salary: USD 200,000 - 240,000 / annual
Shepherd is a Managing General Underwriter (MGU) building an AI-native commercial insurance platform focused on construction and energy risk. The company has raised $67M+ including a $42M Series B led by Intact Private Capital and is backed by Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.
Shepherd is launching a Subcontractor Default Insurance (SDI) product to expand its Construction vertical. The Subcontractor Default Underwriting Lead will play a foundational role in building and shaping this new product line, defining underwriting strategy, go-to-market approach, and driving long-term profitable growth.
In this role, you will:
- Define Shepherd's SDI strategy, including target contractor profiles, construction sectors, program sizes, limits, retentions, geographies, appetite, and growth/loss-ratio targets
- Establish underwriting guidelines, authority framework, referral rules, and rating approach
- Work with capacity partners to secure and structure reinsurance capacity
- Partner with Product, Engineering, and Data teams to design submission-to-bind workflows, financial analysis tools, and portfolio views
- Underwrite new and renewal SDI programs, including financial review and prequalification audits
- Set up monitoring procedures for in-force programs and take action when risk changes
- Own premium, profit, loss-ratio, and retention results for the book
- Leverage broker relationships to drive submission flow and actively market the SDI product at industry events
- Hire, coach, and grow a team of SDI underwriters as the book scales
- Track construction market trends to keep Shepherd profitable and competitive
- Collaborate cross-functionally with Risk Engineering, Actuarial, Corporate Underwriting, Claims, Customer Experience, and Finance
The role is based in San Francisco, NYC, Chicago, LA, or Dallas-Fort Worth, with approximately 25% travel to meet brokers, partners, and the team.
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, including reviewing contractor financial statements, work-in-progress (WIP) schedules, backlog, working capital, and bank lines
- Deep understanding of how general contractors prequalify, select, and manage subcontractors, and ability to evaluate the strength of contractor 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
- Established broker relationships at 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 and ability to make sound decisions with incomplete information
- Willingness to travel approximately 25%
- Bachelor's degree or equivalent experience (background in construction accounting, finance, or law is a plus)
