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Salary: USD 250,000 - 350,000 / annual
Shepherd is a Managing General Underwriter (MGU) building an AI-native commercial risk platform that combines underwriting expertise with automation and data. The company has raised over $67M and is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. Shepherd currently operates in construction and energy segments, writing Primary and Excess Casualty, Builder's Risk, and Workers' Compensation through a nationwide broker network.
Shepherd is launching a Retail Commercial Property vertical and seeking a Commercial Property Underwriting Leader (Director) to build and shape this new business segment from the ground up. This role offers the opportunity to define underwriting strategy, go-to-market approach, and drive long-term profitable growth for a core pillar of the business.
In this position, you will define the production strategy for retail commercial property, including target classes, TIV bands, geographies, appetite, and growth/loss-ratio targets. You'll support development of underwriting guidelines, authority frameworks, referral rules, and rating approaches. You'll partner with Product, Engineering, and Data teams to design the submission-to-bind workflow, pricing tools, and CAT-exposure views. You'll underwrite new and renewal primary and excess property within your authority, own premium/profit/loss-ratio/retention/expense results for the vertical, and leverage your retail broker relationships to drive submission flow. As the vertical scales, you'll hire, coach, and grow a team of property underwriters and support staff. You'll work with Corporate Underwriting on letters of authority and underwriting audits, and collaborate with Claims, Actuarial, Customer Experience, and Finance to ensure the business is underwritten, serviced, and reported well.
The role is based in New York City, San Francisco, Chicago, Los Angeles, or Dallas-Fort Worth, with approximately 25% travel to meet brokers, partners, and the team.
REQUIREMENTS:
- 10+ years of commercial property underwriting experience with deep expertise in retail middle market and large accounts across classes such as real estate, retail, hospitality, manufacturing, and technology
- Proven record of profitable growth: quoting, binding, and building a property book while managing to loss-ratio and combined-ratio targets
- Strong technical command of risk selection, COPE analysis, valuation, pricing, coverage, primary and excess layering, and manuscript forms
- Hands-on CAT modeling experience (RMS/AIR/Verisk) and disciplined aggregate and exposure management
- Established retail broker relationships at regional and national levels 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
