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Senior Builders Risk/Inland Marine Underwriter

June 5, 2026

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: <ul><li>Complex commercial construction projects routinely wait weeks for a single quote</li><li>Legacy carriers rely on static applications and disconnected systems</li><li>Brokers chase carriers through calls, emails, and resubmissions </li></ul>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: <ul><li>Faster decisions</li><li>Smarter, more accurate pricing</li><li>Better risk outcomes for insureds who invest in safer practices </li></ul>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: <ul><li>Intact Private Capital</li><li>Spark Capital</li><li>Costanoa Ventures</li><li>Y Combinator</li><li>Susa Ventures</li><li>And several others </li></ul>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… <ul><li>You have a minimum of 5+ years of previous experience in the commercial underwriting space (Construction, Casualty, and/or Builder's Risk experience preferred)</li><li>You aren’t afraid of ambiguity</li><li>You have a strong work ethic, are self-motivated, and have the ability to manage multiple tasks/projects simultaneously</li><li>You have exceptional interpersonal skills (verbal and written) and a high EQ</li><li>You have strong sales and marketing skills and are able to position accounts and close deals</li><li>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</li><li>Bachelor’s degree or equivalent experience </li></ul>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. <ul><li>Teamwork, communication, and negotiation skills are required. </li><li>Solid background in risk analysis and experience with construction and/or casualty underwriting. </li><li>Knowledge and proficiency with compliance, coverage, products and pricing strategies. </li><li>Be adaptable and creative in a fast paced startup environment </li></ul>This is an onsite position in our New York City, San Francisco, Chicago, Los Angeles, 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 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 Compensation Range: $160K - $205K

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...