Executive Underwriter

What we do

Build the insurance behind the physical world.

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.

Real problems. Real ownership.

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 around them. Join us to build systems whose decisions help real projects get built.

630+ customers / $500B+ insured project value

Our investors

Capital to build. Partners to grow with.

$67M total funding / $42M Series B in March 2026

Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M.

Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer.

A bigger opportunity ahead

We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible.

Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both.

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 7+ 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, 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 Healthcare
100% contribution to health, dental, and vision

Fertility benefits and family building support

️ Flexible PTO
Flexibility to take the time off, recharge, and perform

Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

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

Professional Development
Access to premium coaching, including leadership development

Competitive 401(k) Plan

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