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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 focused on reshaping the future of insurance. They are seeking a Senior Product Manager who will conduct market research, engage with customers ...

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 ...

Corgi Insurance

Head of People

Chicago, IL · On-site

$160K - $230K/yr

About Corgi Corgi is a full-stack insurance carrier building better, faster insurance products for ... a high-growth startup * Strong sourcing chops, going beyond LinkedIn and close competitive ...

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Insurance Startup information

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 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 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.

Billing Operations Intern (Summer)

Beagle Insurance

Chicago, IL • On-site

$4.0K/mo

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 14 days ago

Job description

Beagle, Corgi's renters insurance compliance platform, is hiring a Billing Operations Intern for the summer. You'll work inside our Insurance Operating System (IOS). It's hands-on, detail-heavy work at the core of how we bill thousands of units, ideal for someone precise and organized who wants real operational experience at a fast-growing startup.

What You'll Do

  • Pull and review charge reports from our systems.
  • Maintain records in our Insurance Operating System (IOS) — data entry and clean-up.
  • Support the billing operations team with day-to-day accuracy checks.

What We're Looking For

  • Sharp attention to detail and a strong instinct for data accuracy.
  • Comfortable working in spreadsheets and internal software tools.
  • Organized and reliable, able to own repetitive but important work.
  • Currently pursuing or recently completed a degree (any major welcome).
  • Available full-time, on-site in Dallas, for the summer.
  • Must be legally authorized to work in the U.S.

Compensation & Perks

  • $4,000/month, paid summer internship.
  • Hands-on experience with real billing and insurance operations.
  • Mentorship and direct exposure to a fast-scaling insurtech team.
  • Stocked office and regular team events.
  • Pathway to full-time for strong performers — confirm

Why Work Here?

Beagle is one of the fastest-growing names in insurance tech. You'll get real ownership and hands-on experience at startup speed, doing work that directly supports how we bill thousands of units — not busywork.

Looking for a summer where your work actually matters? Apply today.

Company Description

Beagle is the autopilot for renters insurance compliance, trusted by 1,000+ property managers. We're scaling fast and building enterprise-grade compliance tools without the enterprise-grade complexity.