Why This Job is Featured on The SaaS Jobs
Shepherd sits in a growing SaaS category where software and data are being applied to traditionally manual financial workflows, in this case commercial insurance underwriting. The role stands out because it is anchored in a product-led approach to risk assessment, where decision quality and turnaround time are shaped by platform capabilities and integrations rather than only by carrier process.
For a SaaS career, this kind of position builds fluency in how domain expertise translates into scalable workflows. It offers proximity to AI-assisted operations, partner ecosystems, and the feedback loop between real-world outcomes and product iteration. Experience gained here tends to travel well across vertical SaaS businesses that rely on complex compliance, pricing, and risk decisions, especially where go-to-market success depends on credibility with specialist buyers.
This role is best suited to an underwriter who enjoys operating at the intersection of commercial judgment and systems thinking. It will fit someone comfortable collaborating across technical and business stakeholders, and who prefers roles where negotiation, producer management, and process improvement sit alongside core underwriting work. Onsite expectations also signal a preference for high-touch coordination with internal teams and external partners.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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:
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. Our investors:
Our Team
We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.
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
Benefits
🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision
🥕 Fertility benefits and family building support
🏖️ Unlimited 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
