Commercial Casualty Underwriting Leader (Director)

About the role

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 broker partners and pricing that reflects the actual risk. Shepherd started in construction and energy — two of the most complex and highest-hazard segments in commercial insurance — writing Primary and Excess Casualty, Builder's Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. The mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation. Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital, which also provides capacity across Shepherd's insurance products. Additional investors include Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.

Shepherd is launching a Retail Commercial Casualty vertical as an expansion to its current Primary and Excess Casualty offerings. The Commercial Casualty Underwriting Leader will play a lead role in building and shaping new industry segments from the ground up, defining underwriting strategy, go-to-market, and driving long-term profitable growth for a core pillar of Shepherd's business. This position is based in New York City, San Francisco, Chicago, Los Angeles, or Dallas–Fort Worth offices, with willingness to travel about 25% to meet brokers, partners, and the team.

Responsibilities

• Define the strategy for retail commercial casualty, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth and loss-ratio targets.
• Support the development of underwriting guidelines, authority framework, referral rules, and rating approach.
• Partner with Product, Engineering, and Data to design the submission-to-bind workflow, pricing tools, and exposure and loss-trend views.
• Underwrite new and renewal primary and excess casualty within your authority.
• Own premium, profit, loss-ratio, retention, and expense results for the vertical.
• Use retail broker relationships to drive submission flow in the first year, and serve as Shepherd's senior casualty voice with brokers, clients, and other stakeholders.
• Hire, coach, and grow a team of casualty underwriters and support staff as the book scales.
• Work with Corporate Underwriting to help set letters of authority, run underwriting audits, and coach from the results.
• Work with Claims, Actuarial, Customer Experience and Finance so the business is underwritten, serviced, and reported well.

Qualifications

• 10+ years of commercial casualty underwriting, 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: 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 such as large deductibles and 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 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: ability to make sound decisions with incomplete information and adapt quickly as the business evolves.
• Bachelor's degree or equivalent experience.

Pay

The base salary range for this role is $250,000 – $350,000, plus an annual performance bonus and equity in Shepherd. Offers within the range depend on location, experience, and the relationships and market following you bring.

Benefits

• Premium Healthcare: 100% contribution to top-tier health, dental, and vision
• Fertility Benefits & Family Building Support
• Unlimited PTO: Flexibility to take the 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 (San Francisco office)

Schedule

Full-time, based in one of Shepherd's offices (New York City, San Francisco, Chicago, Los Angeles, or Dallas–Fort Worth) with approximately 25% travel required to meet brokers, partners, and the team.