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Insurtech Chicago Jobs in California (NOW HIRING)

Insurtech Chicago information

What types of projects do professionals typically work on in insurtech roles in Chicago?

In Insurtech roles in Chicago, professionals often collaborate on innovative projects such as developing digital insurance platforms, implementing data analytics for risk assessment, and creating customer-centric mobile applications. Teams are usually cross-functional, bringing together software developers, data scientists, product managers, and insurance experts to address industry challenges. The dynamic environment encourages continuous learning and adaptation to new technologies, offering plenty of opportunities for professional growth and advancement within both startups and established insurance companies.

What are the key skills and qualifications needed to thrive in an insurtech role in Chicago?

To thrive in an Insurtech role in Chicago, you need a solid understanding of insurance fundamentals, data analytics, and technology integration, often backed by a degree in business, finance, or computer science. Familiarity with insurtech platforms, digital claims processing systems, and data analysis tools like SQL or Python is typically required. Strong problem-solving, adaptability, and communication skills help professionals navigate a rapidly evolving industry and collaborate with cross-functional teams. These competencies are crucial for driving innovation and efficiency in Chicago’s competitive insurance technology market.

What is Insurtech Chicago?

Insurtech Chicago refers to the community and ecosystem of insurance technology (insurtech) companies, startups, investors, and professionals based in Chicago. This group focuses on leveraging technology to innovate and improve the insurance industry, from customer experience to underwriting and claims management. Insurtech Chicago often hosts networking events, conferences, and educational sessions to connect industry leaders and foster collaboration. The city is becoming a hub for insurtech due to its strong financial sector, talent pool, and supportive business environment.

What is the difference between Insurtech Chicago vs Insurance Underwriter?

AspectInsurtech ChicagoInsurance Underwriter
CredentialsTypically requires a bachelor’s degree in business, finance, or related fieldsRequires a bachelor’s degree; certifications like CPCU or ARM are common
Work EnvironmentTech-driven startups, insurance technology companies, innovation hubsInsurance companies, underwriting departments, corporate offices
Industry UsageFocuses on insurance technology solutions, digital platforms, and innovationFocuses on evaluating risks, pricing policies, and approving coverage

Insurtech Chicago involves working within technology-focused insurance companies or startups, emphasizing innovation and digital solutions. In contrast, Insurance Underwriters primarily assess risks and determine policy terms within traditional insurance firms. Both roles require similar educational backgrounds and industry knowledge but differ in work environment and focus areas.

What are popular job titles related to Insurtech Chicago jobs in California? For Insurtech Chicago jobs in California, the most frequently searched job titles are:
What job categories do people searching Insurtech Chicago jobs in California look for? The top searched job categories for Insurtech Chicago jobs in California are:
What cities in California are hiring for Insurtech Chicago jobs? Cities in California with the most Insurtech Chicago job openings:

Staff Software Engineer (SF)

Shepherd Labs Inc.

San Francisco, CA • On-site

$230K - $260K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 3 days ago

New


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:
  • 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. Our investors:
  • Intact Private Capital
  • Spark Capital
  • Costanoa Ventures
  • Y Combinator
  • Susa Ventures
  • 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

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