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Corgi Insurance

Strategic Projects

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In-Office
Chicago, IL, USA
100K-180K Annually
In-Office
Chicago, IL, USA
100K-180K Annually

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At Corgi, we're building the first fully automated insurance carrier.

Our goal is to rebuild the $1T+ insurance industry from the ground up using AI. We're not just building a company; we're building infrastructure for the next hundred years. If you’ve built things from scratch and know what it means to move fast and own outcomes, we want you on the team.
We’re well-funded and backed by top investors, providing the resources you wish you had when building your own business. We don’t care about traditional roles or titles - just that you’re smart, proactive, and bring the same founder-level ownership and drive to help us build something massive.
This is not a traditional role. You’ll work across everything: new product lines, regulatory filings, recruiting, office setup, partnerships, special ops, and whatever else it takes to scale Corgi. Your title won’t matter. Results will.

What You'll Do

  • Own high-stakes strategic projects end-to-end (filings, launches, hiring, real estate, ops)

  • Stand up new initiatives quickly and independently

  • Navigate regulators, vendors, and partners with confidence

  • Recruit top talent and help build the physical and cultural infrastructure of Corgi

  • Ship fast, operate with little oversight, and figure it out

What We're Looking For

  • You’ve started or built something from zero (startup, team, org, product, community)

  • You move fast, prioritize well, and get things done

  • You thrive in chaos and ambiguity—build the plan while running it

  • You don’t care about job titles, just about winning

  • You’re obsessive about quality and impact

Why Join Corgi

  • Founder Mentality: We value extreme ownership. Think like a founder, not an employee.

  • Ground Floor: Help build a $100B+ company from day one with real resources behind you.

  • Speed & Impact: See your work make a difference—now, not later.

Our Perks

💸 Competitive pay and equity

👩‍🍳 Private chef (lunch, dinner, and snacks)

🐕 Office Corgi

🏥 Medical/dental/vision insurance

🍯 Unlimited honey from our own bees

🎆 Weekly team fun events

🛏️ Your own Costco mattress

Still Interested?

Make us believe you’re serious. Send a 1-minute video introducing yourself and include:

  • What startups or projects you’ve built or worked on

  • Something you’re proud of

  • What drives you

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

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