Startups · AI

Commercial Casualty Underwriting Leader (Director)

Shepherd · San Francisco · On-site

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About Shepherd

The all-in-one learning co-pilot. Backed by Y Combinator.

About the role

Shepherd's underwriting approach is client-centric with a heavy emphasis on an efficient process. Our goal is to leverage our technology and data to make quick, informed underwriting decisions tailored to our clients' specific needs. Define the strategy for retail commercial casualty, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth and loss-ratio targets. Found on 1752vc Careers, the job board for startup and VC roles.

What they're looking for

  • 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
  • A 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
More about this role

The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth.

Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen.

We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us.

Our engineers, designers, underwriters, CX, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work.

The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work...

Read the full posting on Shepherd's site ↗

Underwriting

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