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Insurance Startup Jobs in Chicago, IL (NOW HIRING)

Vouch, Inc.

Insurance Advisor

Chicago, IL · On-site

$85K - $90K/yr

We're a quickly growing startup that believes in transparency and acknowledgment with our team ... Insurance Advisors interact directly with our clients through email, video calls, and other ...

Honeycomb Insurance

Software Engineer

Chicago, IL · On-site

$140K - $170K/yr

Honeycomb Insurance At Honeycomb, we're not just building technology; we're reshaping the future of ... Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered ...

Honeycomb Insurance

Senior Underwriter, Midwest

Chicago, IL · On-site

$101K - $120K/yr

Honeycomb Insurance At Honeycomb, we're not just building technology; we're reshaping the future of ... Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered ...

Honeycomb Insurance

Senior Product Manager

Chicago, IL · On-site

$130K - $172K/yr

Honeycomb Insurance At Honeycomb, we're not just building technology; we're reshaping the future of ... Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered ...

Honeycomb Insurance

Senior Product Manager

Chicago, IL · On-site

$130K - $172K/yr

Honeycomb is a rapidly growing global startup reshaping the future of insurance. The Senior Product Manager will conduct market research, engage with customers, and collaborate with cross-functional ...

Honeycomb Insurance

Senior Product Manager

Chicago, IL · On-site

$130K - $172K/yr

Honeycomb Insurance is a rapidly growing global startup that is reshaping the future of insurance. They are seeking a Senior Product Manager to conduct market research, engage with customers ...

Kin Insurance, Inc.

Senior Financial Analyst

Chicago, IL · On-site

$90 - $120/hr

Insurance, fintech, or high‑growth startup experience How We Hire We believe a great hiring experience should be clear, respectful, and human. We will accept applications for this position until ...

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All JobsInsurance Startup JobsInsurance Startup Jobs in Chicago, IL

Insurance Startup information

What is an insurance startup?

An Insurance Startup job typically involves working for a newly established company in the insurance industry, focusing on innovation and disruptive solutions. Roles can range from product development and underwriting to sales, marketing, and technology-driven initiatives like insurtech. Employees in these roles often work in a fast-paced environment, helping to build new products, automate processes, or improve customer experiences. Since startups are growth-oriented, employees may take on diverse responsibilities and have opportunities for rapid career progression.

What does a typical workday look like at an insurance startup?

Working at an insurance startup involves a mix of tasks, from developing and refining insurance products to liaising with partners, clients, and regulators. Your day may include market research, pitching new solutions to prospective clients, managing tech integrations, and collaborating closely with a small, agile team. Expect a fast-paced environment where you'll juggle multiple responsibilities and contribute directly to the company's direction and success. You'll also have opportunities to learn from industry experts and take on increasing responsibility as the business grows.

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

To thrive in an Insurance Startup, you need a blend of entrepreneurial drive, industry knowledge, and strong business development skills, often supported by experience in insurance, finance, or related fields. Familiarity with insurtech platforms, CRM systems, and compliance regulations is highly valued. Exceptional problem-solving, adaptability, and networking abilities set top performers apart in dynamic startup environments. These skills are essential for navigating regulatory complexity, identifying growth opportunities, and building a successful insurance business from the ground up.

What are popular job titles related to Insurance Startup jobs in Chicago, IL?

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

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

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

Insurance Startup jobs near you
Infographic showing various Insurance Startup job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 89% In-person, and 11% Remote job distribution.

4th Engineer / Onsite Chicago / Python / Healthcare Startup

Chicago, IL • On-site

Motion Recruitment Partners, LLC
Recruiting and Staffing Services • 1 - 5K employees
Learn more about Motion Recruitment Partners, LLCexternal

Other

Medical, Dental, Vision, PTO

Posted 11 days ago

Job description

A Chicago-based healthcare technology startup is seeking their 4th full-time Senior Software Engineer to help build AI-powered products that improve access to behavioral healthcare. This venture-backed organization is leveraging modern AI technologies, LLMs, and full-stack engineering to solve complex operational challenges within the healthcare system. The position is primarily based in downtown Chicago with flexibility for exceptional candidates willing to spend significant time collaborating with the team in person in River North.
This is a rare opportunity to join an exceptionally small engineering team and influence the company during its earliest stages of growth. The ideal candidate is a hands-on builder who thrives in startup environments, enjoys moving quickly, and wants meaningful ownership over both product and technical decisions. This team likes to have fun, but in this stage they need someone who is willing and able to dedicate 60+ hours a week to being hands-on writing code while contributing to shaping architecture, engineering processes, and the future direction of the platform, working directly alongside company founders. Required Skills & Experience
  • 4+ years of professional software engineering experience
  • Ability to work 60+ hours per week, including occasional weekends
  • Experience in early-stage startups or high-growth environments
  • Full-stack development experience
  • Strong proficiency with modern web technologies
  • Experience building and shipping customer-facing applications
  • Demonstrated project ownership from concept to deployment
  • Experience collaborating closely with product and business stakeholders
  • Strong communication and problem-solving skills
  • Ability to work independently in fast-changing environments
Desired Skills & Experience
  • Previous Founding Engineer or early engineering hire experience
  • Experience with LLMs, AI agents, or generative AI products
  • Startup leadership or mentoring experience
  • Healthcare or health-tech exposure
  • Experience designing scalable systems and technical architecture
  • Familiarity with cloud infrastructure and DevOps practices
  • Experience leveraging AI-assisted development tools
What You Will Be Doing Tech Breakdown
  • 40% Full-Stack Product Development
  • 25% AI & LLM Integrations
  • 20% Platform & Infrastructure Engineering
  • 15% Technical Architecture & System Design
Daily Responsibilities
  • Build and launch AI-powered product features
  • Partner directly with founders to define product direction
  • Design scalable architecture and engineering solutions
  • Own features throughout the entire development lifecycle
  • Contribute to infrastructure, deployment, and operational excellence
  • Help establish engineering best practices as the team grows
  • Evaluate and implement emerging AI technologies where appropriate
  • 80% Hands-On Development, 5% Team Leadership & Mentorship, 15% Cross-Functional Collaboration
The Offer You will receive the following benefits:
  • Competitive base salary
  • Bonus eligible
  • Equity participation with meaningful ownership potential
  • Medical, Dental, and Vision Insurance
  • Paid Vacation Time
  • Stock Options
  • High-impact role within a growing startup
  • Direct access to company leadership
  • Opportunity to influence technology and engineering culture

Applicants must be authorized to work in the U.S. on a full-time basis now and in the future.
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