Startups · AI

Commercial Property Underwriting Leader (Director)

Shepherd · New York City · 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 using our AI-native platform. Our goal is to leverage our technology and data to make quick, informed underwriting decisions tailored to our clients' specific needs. Define the production strategy for retail commercial property, including target classes, TIV bands, 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 property 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: 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 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
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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