# Commercial Property Underwriting Leader (Director) at Shepherd

Shepherd is hiring a Commercial Property Underwriting Leader (Director) in New York, United States. It pays $250k-$350k a year and Level rates it Little AI ●○○○; you can [apply on Level](https://jobsbylevel.com/go/59330fb4-5f7c-4901-9c4b-16795c75238d?utm_medium=ai-agent).

AI Level 1, AI centrality 28 out of 100. New York City.

## Details

- Company: [Shepherd](https://jobsbylevel.com/companies/shepherd)
- AI level: AI Level 1 (score 28 out of 100)
- Location: New York City
- Salary: $250k-$350k
- Posted: October 19, 2026
- Apply: https://jobsbylevel.com/go/59330fb4-5f7c-4901-9c4b-16795c75238d?utm_medium=ai-agent

## Description

What We Do Commercial insurance still runs on processes built decades ago. Underwriting is slow, and pricing leans on broad averages instead of the specifics of each risk. Technology can change how commercial risk is priced and managed, as long as it's paired with real underwriting expertise. The companies that get this right will shape the next era of the industry, and Shepherd intends to lead it. 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 our broker partners and pricing that reflects the actual risk. We started where the gap is widest: construction and energy, two of the most complex and highest-hazard segments in commercial insurance. Today we write Primary and Excess Casualty, Builder’s Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. Our mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation. 🚀 Our Investors Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital. Intact also partners with Shepherd to provide capacity across its insurance products. Shepherd is also backed by leading institutional investors, including Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. Commercial Property Underwriting Leader (Director) Shepherd is launching a Retail Commercial Property vertical as an expansion to its current Property and Inland Marine offerings. The Commercial Property Underwriting Leader will play a lead role in building and shaping new industry segments from the ground up. This is an opportunity to help define the underwriting strategy, go-to-market, and drive long-term profitable growth for a core pillar of Shepherd’s business. We're looking for someone with 10+ years of commercial property underwriting experience, a proven track record of leadership, deep relationships in the retail channel, and an entrepreneurial mindset who is excited to build something new with modern technology and a forward-thinking team. About you You are a builder who wants to shape the future of commercial insurance and do the best work of your career. You have deep property expertise, a loyal broker network, and the drive to turn a blank page into a profitable book. You'd be a great fit if you have: 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. Executive presence to present strategy and results to leadership, capacity partners, and reinsurers. Comfort with ambiguity: you make sound decisions with incomplete information and adapt quickly as the business evolves. Willingness to travel about 25% to meet brokers, partners, and the team. A bachelor's degree or equivalent experience. 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. In this role, you will: Define the

The description is cut here. Read the full offer: https://jobsbylevel.com/jobs/commercial-property-underwriting-leader-director-at-shepherd-3097dc

Source: https://jobsbylevel.com/jobs/commercial-property-underwriting-leader-director-at-shepherd-3097dc

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