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Insurtech Jobs in Chicago, IL (NOW HIRING)

At-Bay

Actuarial Manager, Pricing

Chicago, IL

$175K - $205K/yr

Create/improve tools and automate processes to improve the teams operational efficiency Qualifications * 6+ years P&C pricing experience in an insurance company/tech company/Insurtech/consulting ...

Chubb

Enrollment Systems Specialist

Chicago, IL · On-site

$73K - $107K/yr

Support key external strategic partnerships with insurtech vendors, enrollment, and fulfillment firms, focusing on platform strategy and performance. * Serve as the primary contact for sales, brokers ...

TytoCare

Actuarial Manager, Pricing

Chicago, IL · On-site

$175 - $205/hr

Qualifications * 6+ years P&C pricing experience in an insurance company/tech company/Insurtech/consulting company. * ACAS or FCAS certification. * 1+ years serving in a direct managerial, team lead ...

Chubb

Enrollment Systems Specialist

Chicago, IL

$73K - $107K/yr

Support key external strategic partnerships with insurtech vendors, enrollment, and fulfillment firms, focusing on platform strategy and performance. * Serve as the primary contact for sales, brokers ...

At-Bay

Actuarial Manager, Pricing

Chicago, IL · On-site

$175K - $205K/yr

Create/improve tools and automate processes to improve the teams operational efficiency Qualifications * 6+ years P&C pricing experience in an insurance company/tech company/Insurtech/consulting ...

Chubb

Enrollment Systems Specialist

Chicago, IL · On-site

$73K - $107K/yr

Support key external strategic partnerships with insurtech vendors, enrollment, and fulfillment firms, focusing on platform strategy and performance. * Serve as the primary contact for sales, brokers ...

Chubb

Enrollment Systems Specialist

Chicago, IL · On-site

$73K - $107K/yr

Support key external strategic partnerships with insurtech vendors, enrollment, and fulfillment firms, focusing on platform strategy and performance. * Serve as the primary contact for sales, brokers ...

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Insurtech information

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How much do insurtech jobs pay per hour?

As of Aug 19, 2026, the average hourly pay for insurtech in Chicago, IL is $12.55, according to ZipRecruiter salary data. Most workers in this role earn between $10.62 and $13.85 per hour, depending on experience, location, and employer.

What is InsurTech?

Insurtech, short for insurance technology, refers to the innovative use of technology to improve and streamline the insurance industry. This includes leveraging artificial intelligence, big data, mobile apps, and other digital tools to enhance customer experience, speed up claims processing, and create new insurance products. Insurtech companies often focus on making insurance more accessible, affordable, and personalized for consumers, while also helping insurers operate more efficiently. The sector is rapidly evolving and is transforming traditional insurance models.

What are Insurtech jobs?

Insurtech jobs focus on the engineering of software and hardware, the collection and analysis of data, the implementation of cybersecurity, and the development of apps for insurance companies. The duties of IT and software professionals in the Insurtech industry depend on their area of specialization. The responsibilities of a data scientist, for example, revolve around analyzing data that they collect from smartphone apps, tracking devices, and wearables. Hardware and software engineers create these devices and apps and develop their data collection capacity and user interfaces. Software and web developers work on insurance sites and e-marketing tools for insurance companies.

What are the key skills and qualifications needed to thrive in an Insurtech role, and why are they important?

To excel in an Insurtech role, you typically need a strong background in insurance concepts, data analytics, and business or computer science, often supported by a relevant degree. Familiarity with insurance management systems, cloud platforms, and programming languages like Python or SQL, as well as certifications such as CPCU or IT-related credentials, is highly beneficial. Strong problem-solving abilities, adaptability, and effective communication set top performers apart, especially when bridging gaps between technical and business teams. These skills are vital for driving digital transformation, ensuring regulatory compliance, and delivering innovative solutions in a rapidly evolving insurance marketplace.

What are common challenges faced by professionals working in Insurtech roles, and how can they be addressed?

Professionals in Insurtech roles often encounter challenges such as navigating complex regulatory requirements, integrating new technologies with legacy insurance systems, and fostering collaboration between technical teams and traditional insurance experts. Addressing these challenges requires continuous learning about the evolving regulatory landscape, strong communication skills to bridge knowledge gaps between teams, and a proactive approach to change management. Many Insurtech teams benefit from agile methodologies and cross-disciplinary collaboration to drive innovation while maintaining compliance and client trust.

What is the difference between Insurtech vs Insurance Underwriter?

AspectInsurtechInsurance Underwriter
Required CredentialsTypically a degree in business, technology, or related fields; certifications in insurance or tech are a plusDegree in finance, economics, or actuarial science; professional certifications like CPCU or FCAS often required
Work EnvironmentTech startups, insurance technology companies, or digital platformsInsurance companies, underwriting firms, or brokerage agencies
Employer & Industry UsageUsed by companies innovating insurance processes through technologyTraditional insurance companies and underwriting agencies

Insurtech professionals focus on developing and implementing technology solutions to improve insurance services, while insurance underwriters assess risks and determine policy terms. Both roles require knowledge of insurance principles, but Insurtech emphasizes tech skills, whereas underwriters focus on risk analysis.

More about Insurtech jobs

What are the most commonly searched types of Insurtech jobs in Chicago, IL?

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For Insurtech jobs in Chicago, IL, the most frequently searched job titles are:

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The top searched job categories for Insurtech jobs in Chicago, IL are:

Insurtech jobs near you
Infographic showing various Insurtech job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 69% In-person, and 31% Remote job distribution, with an average salary of $26,114 per year, or $12.6 per hour.

VC Principal @ Distributed Ventures in Chicago, IL

VC Stack

Chicago, IL • On-site

$120 - $180/hr

Other

Medical, Dental, Vision, Retirement

Posted yesterday

New

Job description

About Us

At Distributed Ventures, we understand the confines of risk and the opportunities it provides for innovation within Employer Solutions, Insurtech, and Fintech.

Our unparalleled experience and expertise in the risk ecosystem allow us to connect early‑stage companies with the guidance, access, and customers they need to accelerate revenue and rapidly achieve product‑market fit.

We back founders with precision capital, partnering with them to manage and mitigate risk, helping them build technologies and solutions that provide stability in an uncertain world.

About You
  • 5‑7 years of direct experience in venture capital in the investing seat, with prior investment banking or consulting experience in our verticals preferred.
  • Proven track record of sourcing, evaluating, driving and leading successful investments.
  • Obsession with identifying “next big thing” market opportunities in contexts with imperfect information. Often this takes the form of anti‑consensus, high‑conviction investment thesis creation.
  • You are passionate about entrepreneurship and technology. You always find yourself thinking about ideas that are changing the world, and you love supporting founders in achieving their visions.
  • You are intellectually curious and don’t just check things off a list. You ask questions and aren’t afraid to think through all pathways to get to an answer.
  • You love driving to the “so what” when dealing with complex data or ambiguity, but you’re also comfortable navigating unknowns.
  • You can work independently and will proactively prioritize your time towards the most value‑added tasks.
  • You are detail‑oriented and often catch the things that other people miss.
  • You are humble, honest, perceptive and thoughtful.
  • You care about building culture, have a balanced sense of ego, a high output to wordcount balance, and share our “no asshole” policy.
Position Summary

As a Principal, you’ll guide investment in bleeding edge innovations across our focus verticals by supporting all parts of the deal process, including: leading team members in shaping investment theses, guiding market research and subject‑matter interviews, overseeing due diligence on potential opportunities, and supporting portfolio companies after investment.

Further, you will play a key role in creating a dynamic culture across the team by investing in others’ development, sharing best practices, and amplifying the impact of all team members in investment contexts.

Location preference will be for Chicago.

What You’ll Do
  • Deal Sourcing:
    • Source and evaluate new investment opportunities through research, networking, and relationship building.
  • Investment:
    • Lead due diligence processes, including market analysis, financial modeling, and risk assessment.
    • Develop and present investment recommendations to the Investment Committee.
    • Drive structure and execute investment transactions as the primary point person, in collaboration with the managing partner and other team members.
  • Portfolio Support:
    • Act as a key advisor to portfolio companies, supporting strategic initiatives, fundraising, and scaling efforts.
  • Ecosystem Building:
    • Build and maintain relationships with entrepreneurs, co‑investors, and industry stakeholders.
    • Develop and maintain relationships with current and future potential limited partners.
    • Build and maintain relations with ecosystem partners – payers, brokers/consultants, health systems, providers, etc.
  • Platform:
    • Mentor team members and contribute to internal knowledge sharing and team development.
    • Own and/or build on existing fund processes and knowledge base, especially with regards to investment theses.
What We Offer
  • Competitive salary and bonus to be shared during the process.
  • Full benefits, including medical, dental, vision and 401k match.
  • Flexible time off policy.
  • Note: unfortunately, we cannot sponsor visas at this time.
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