Insurtech Chicago Jobs in California (NOW HIRING)

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. Our investors:

• 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.
The Role
We're looking for a talented staff software engineer who's passionate about what we're building and ready to do the best work of their career. You thrive on ownership, drive results, and care deeply about both technical excellence and customer impact.
You would be our dream candidate if...

• You aren't afraid of ambiguity, and it may even excite you
• You enjoy shipping product every day (maybe multiple times a day) while maintaining high quality standards
• You enjoy wearing multiple hats while solving problems; as an engineer, product manager, and designer
• You take end-to-end ownership of features and systems, from conception through release
• You care about the built-world and how to improve construction safety and productivity
• You care about others' growth and welcome mentoring other engineers - you've led or been a major contributor on significant projects
• You have strong opinions, weakly held - you advocate for your ideas but adapt when presented with better solutions
• You communicate technical concepts clearly to both technical and non-technical stakeholders
• You have some experience with insurance - either from a prior InsurTech role or actuarial role
• You have experience working with Javascript/Typescript (backend and/or frontend)
• You have at least 8+ years of working experience (preferably as a full-stack engineer) with a track record of delivering high-impact products

About the Role
Shepherd's platform consists of three primary elements: data collection, automated underwriting, and policy administration.

• You will lead major initiatives and own a large area of Shepherd's product experience, in each vertical while driving technical decisions for your domain
• You will work across the stack, even across different disciplines (e.g. underwriting, design, product management)
• You will play an integral role in building our culture as the company grows and mentor other engineers as we scale the team
• You will balance innovation with pragmatic delivery - staying current with emerging tech while shipping quality products
• You will contribute to product strategy and architectural decisions, not just implementation
• You will collaborate closely with PM, Mo (CTO) and the insurance team (underwriters, actuaries and more!)

Our Tech Stack
Frontend

• React & Next.js
• Typescript
• GraphQL w/ Apollo

Backend

• Node.js
• Postgres & Redis
• Typescript
• GraphQL APIs

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
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