Senior Underwriter

Shepherd; Chicago (IL); On-site; USD 160,000 - 205,000; Full time

Benefits offered by this job

Premium Healthcare

Fertility benefits and family building

Unlimited PTO

Daily lunches, dinners, and snacks

Offices: SF, NYC, Dallas‑Fort Worth, /

Professional Development

Competitive 401(k) Plan

Dog-friendly office

Job summary

Shepherd is a technology-driven Managing General Underwriter transforming commercial Property & Casualty insurance for high-hazard industries. The role focuses on underwriting excellence, rapid decisions, and pricing accuracy in a fast-paced startup environment.

You will market, manage producers, develop new business, and negotiate with partners to align with Shepherd's underwriting appetite. We require 5+ years in commercial underwriting (Construction/Casualty/Builder’s Risk), strong

Qualifications

• Minimum 5+ years in commercial underwriting (Construction, Casualty, Builder's Risk preferred).
• Not afraid of ambiguity and able to manage multiple tasks.
• Excellent verbal and written interpersonal skills, high EQ.
• Strong sales and marketing capability to position accounts and close deals.
• Underwriting duties include developing/negotiating price, coverage, terms for new business & renewals; identify target accounts.

Responsibilities

• Market, manage producers, develop new business and negotiate with internal and external partners.
• Demonstrate teamwork, communication and negotiation skills.
• Background in risk analysis with construction and/or casualty underwriting.
• Knowledge of compliance, coverage, products and pricing strategies.
• Be adaptable and creative in a fast-paced startup environment.

Skills

Commercial underwriting

Builder's Risk

Construction underwriting

Sales & marketing

Negotiation

Ambiguity management

Interpersonal skills

Education

Bachelor's degree or equivalent experience

Job description

What We Do

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. 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.

We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:

• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes

With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important industries and the progress they make possible.

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, led our Series B round
• Costanoa Ventures, led our Series A round
• Spark Capital, led our Seed round
• Susa Ventures, lead our Pre-Seed round
• Y Combinator
• And several others

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.

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. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.
• 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 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
• Offices: 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