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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 technology and data to accelerate decisions and improve pricing accuracy. The company has raised over $67M (Series B led by Intact Private Capital) and focuses on complex, high-hazard segments including construction and energy, writing Primary and Excess Casualty, Builder's Risk, and Workers' Compensation through a nationwide broker network.
Shepherd is launching a new Retail Commercial Casualty vertical and seeking a Commercial Casualty Underwriting Director to build and shape this segment from the ground up. This is a leadership role responsible for defining underwriting strategy, go-to-market approach, and driving profitable growth for a core business pillar.
In this role, you will:
- Define strategy for retail commercial casualty, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth/loss-ratio targets
- Support development of underwriting guidelines, authority frameworks, referral rules, and rating approaches
- Partner with Product, Engineering, and Data teams to design submission-to-bind workflows, pricing tools, and exposure/loss-trend analytics
- Underwrite new and renewal primary and excess casualty within your authority
- Own premium, profit, loss-ratio, retention, and expense results for the vertical
- Leverage established retail broker relationships to drive submission flow and serve as Shepherd's senior casualty voice with brokers, clients, and stakeholders
- Hire, coach, and grow a team of casualty underwriters and support staff as the book scales
- Work with Corporate Underwriting to set letters of authority, run audits, and coach from results
- Collaborate with Claims, Actuarial, Customer Experience, and Finance to ensure proper underwriting, servicing, and reporting
The role is based in San Francisco, New York City, Chicago, Los Angeles, or Dallas-Fort Worth, with approximately 25% travel expected.
REQUIREMENTS:
- 10+ years of commercial casualty underwriting experience with deep expertise in retail middle market and large accounts across classes such as real estate, retail, hospitality, manufacturing, and technology
- Proven track 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 (large deductibles, 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 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
