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.

About You

We are looking for a motivated and eager individual who’s passionate about the future of construction and eager to do the best work of their career.

You would be a dream candidate if…

• You have a minimum of 5+ years of previous experience in the commercial underwriting space (Construction, Casualty, and/or Builder's Risk experience preferred)

• You aren’t afraid of ambiguity

• You have a strong work ethic, are self-motivated, and have the ability to manage multiple tasks/projects simultaneously

• You have exceptional interpersonal skills (verbal and written) and a high EQ

• You have strong sales and marketing skills and are able to position accounts and close deals

• Underwriting duties will include developing and negotiating price, coverage, terms and conditions for all new business and renewals while actively identifying target accounts that fit Shepherd’s underwriting appetite

• Bachelor’s degree or equivalent experience

About the Role

Shepherd's underwriting approach will be client-centric with a heavy emphasis on an efficient process. Our goal will be to leverage our technology and data to make quick, informed, underwriting decisions tailored to our client's specific needs.

Candidates must be able to demonstrate success in marketing, producer management, new business development, and the ability to successfully negotiate on all levels with both internal and external partners.

• Teamwork, communication, and negotiation skills are required.

• Solid background in risk analysis and experience with construction and/or casualty underwriting.

• Knowledge and proficiency with compliance, coverage, products and pricing strategies.

• Be adaptable and creative in a fast paced startup environment

This is an onsite position in our New York City, San Francisco, Chicago, Los Angeles, or Dallas Fort Worth offices.

#LI-Onsite

How we work

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. Come set a standard the rest of the team inherits.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

Benefits 

Premium Healthcare100% contribution to top-tier health, dental, and vision

Fertility benefits and family building support

️ Unlimited PTOFlexibility to take the time off, recharge, and perform

Daily lunches, dinners, and snacksWe work together, and enjoy meals together too

️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

Professional DevelopmentAccess to premium coaching, including leadership development

Competitive401(k) Plan

Dog-friendly officePlenty of dogs to play with and make friends with in the SF office