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Insurtech Jobs in Chicago, IL (NOW HIRING)

Akur8

Senior Reserving Actuary

Chicago, IL · Remote

$170K - $230K/yr

Akur8 is a fast-growing InsurTech scale-up on a mission to redefine insurance pricing and reserving through transparent, high-performance modeling technology. Our SaaS platform uses transparent ...

Akur8

Pricing Actuary

Chicago, IL · Remote

$170K - $220K/yr

Akur8 is a fast-growing InsurTech scale-up on a mission to redefine insurance pricing and reserving through transparent, high-performance modeling technology. Our SaaS platform uses transparent ...

HUB

Management Liability Specialist

Chicago, IL · On-site +1

$60K - $100K/yr

We've become one of the most prominent companies in the Insurtech revolution by challenging conventional thinking and finding unconventional solutions to the industry's problems. Our efforts have ...

Symmetry

Remote Sales and Team Builder

Chicago, IL · On-site +1

$20K - $60K/mo

We offer a rare mix of world-class product leadership and insurtech, outstanding corporate support, and rapid customer traction combined with a vision big enough to change the world. Mank welcomes ...

Symmetry

Remote Sales and Team Builder

Chicago, IL · Remote

$20K - $60K/mo

We offer a rare mix of world-class product leadership and insurtech, outstanding corporate support, and rapid customer traction combined with a vision big enough to change the world. Mank welcomes ...

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 ...

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 ...

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Insurtech information

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How much do insurtech jobs pay per hour?

As of Aug 26, 2026, the average hourly pay for insurtech in Chicago, IL is $12.56, according to ZipRecruiter salary data. Most workers in this role earn between $10.67 and $13.89 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

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

What job categories do people searching Insurtech jobs in Chicago, IL look for?

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 67% In-person, and 33% Remote job distribution, with an average salary of $26,134 per year, or $12.6 per hour.

Strategy & Operations Lead - AI Insurtech

Mundelein, IL • On-site

RecruiterForceAI
See more jobs at RecruiterForceAIexternal

$100K - $150K/yr

Other

Posted 2 days ago

New

Job description

About the Role

One of the fastest-growing AI companies in insurtech is looking for a sharp Strategy & Operations professional to help scale its claims operations from the ground up. With multi-seven-figure ARR hit in under a year, ~50% MoM growth, and a $50M Series A just closed from Bessemer Venture Partners — this is a rare chance to get in early at a company with genuine $100B+ potential.

You'll work directly with the CEO, owning high-impact initiatives and building the operational backbone of a business redefining how insurance claims are handled at scale. This is a fast-track into leading a core business area with real ownership and a mandate to build your own team.

What You'll Do

  • Own special projects and strategic initiatives working directly with the CEO
  • Build and formalise claims operations as the company scales rapidly — process design, hiring, workflows
  • Design scalable, data-driven processes that optimise product workflows
  • Lead cross-functional problem solving across product, engineering, and business teams
  • Context-switch across diverse, high-impact initiatives, bringing structure and clarity to each

What We're Looking For

  • 2+ years in MBB consulting, investment banking, private equity, or a strategic operations role at a top-tier startup
  • Exceptionally structured, data-driven thinker with strong attention to detail
  • Based in or willing to relocate to San Francisco (5 days in-office)
  • Strong cross-functional communicator who builds trust quickly across customers, teammates, and partners
  • High-intensity operator who thrives in ambiguous, fast-moving environments

Why Join?

  • 🚀 Massive traction: Multi-seven-figure ARR in under a year with ~50% MoM growth and a $50M Series A from Bessemer — on top of a 13x oversubscribed seed from Founders Fund and Emergence Capital
  • 🏦 Enormous market: Insurance is a $280B industry. This company is building the AI-native claims processor to capture it
  • 🧠 Exceptional team: Engineers from Optiver, DRW, Palantir, and AWS; AI researchers published at NeurIPS/ICML; ICPC and Olympiad winners; operators from Harvard, Berkeley, and Oxford
  • 🏗️ Ground-floor leadership: 2nd hire in Strategy & Ops — direct CEO access with a real path to leading your own business unit
  • 💰 Strong package: $100K–$150K base (with flexibility), competitive equity, all meals covered, comprehensive medical/dental/vision, visa sponsorship, and relocation support
  • Hiring: Up to 5 candidates | Location: San Francisco, CA | Visa & relocation support available

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