Executive Underwriter

What We Do

Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

Complex commercial construction projects routinely wait weeks for a single quote

Legacy carriers rely on static applications and disconnected systems

Brokers chase carriers through calls, emails, and resubmissions

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real‑time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

Faster decisions

Smarter, more accurate pricing

Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

Our Investors

In March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building.

Intact Private Capital

Spark Capital

Costanoa Ventures

Y Combinator

Susa Ventures

And several others

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.

Benefits

Premium Healthcare: 100% contribution to top‑tier health, dental, and vision

Fertility benefits and family building support

Unlimited PTO

Daily lunches, dinners, and snacks

Multiple office locations: SF, NYC, Dallas‑Fort Worth, Chicago and LA

Professional Development: Access to premium coaching, including leadership development

Competitive 401(k) Plan

Dog‑friendly office

Compensation Range: $185K - $228K

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