Reinventing Industry: Mapping the fintech and insurtech landscape in Chicago

Chicago Venture Category Market Maps (4)

Chicago’s fintech and insurtech sectors are on a growth trajectory, with early-stage startups leveraging cutting-edge technologies to redefine these categories. With nearly 70 active ventures and over $300 million of cumulative capital raised, the Windy City has become a dynamic hub for innovations in financial services, insurance, and regulatory tech.

Why combine these two categories? Finance and insurance technologies have several carryovers in their applications. Shared needs around data, behavioral analytics, and tools to more accurately assess risk help the underwriting of insurance policies and more effective/personalized financing products. Secondly, overlap in regulatory demands around compliance, customer data privacy, and fraud detection means players in both sectors often adopt similar tech solutions for KYC, anti-money laundering, and risk management issues.

According to the Global Financial Centres Index, Chicago's financial hub ranks 6th globally and 3rd nationally. The report measures cities' financial sectors on a composite scoring system of 5 broad areas: Business Development, Human Capital, Infrastructure, Financial Sector Development, and Reputation.

Leading companies headquartered in Chicago include Allstate, Discover, Arthur J. Gallagher, One Republic International, and Wintrust, to name a few. Other category leaders that call Chicago home include trading firms like DRW, Optiver and Belvedere, asset management firms like Northern Trust and Invesco, and intelligence platforms like Morningstar. This wide breadth of large players within the city is a key piece of infrastructure driving innovation and attracting local talent.

Key Sub-Categories Driving Growth

  1. AI & Data Tools for Finance and Insurance
    Companies here are harnessing AI and big data to power advanced analytics, automate financial insights, and drive better decision-making. Deloitte's "State of Generative AI in the Enterprise" report indicates that three-quarters of respondents expect generative AI to transform their organizations within three years. Select companies include:
  • Alpathena ($4 million round) - Equips advisors with AI powered tools to deliver customized indexes, advanced tax optimization to clients
  • Clockwork.ai ($3 million round) - AI powered financial modeling software to build out projections and cash flow forecasts in minutes
  • Teragonia ($10 million round) - Decision intelligence system to help businesses optimize price, plan GTM, model churn, and more.

    2. Alternative Assets and Data
    Insurance providers and financial players are constantly on the hunt for improved methods of underwriting risk and generating capital returns. Platforms are enabling retail investors to purchase ownership in alternative assets and aggregating unique data sets for insurance/financing purposes. Select companies include:
  • Assets
    • GameGain (pre-product) - Fractional ownership of sports league
    • FranShares ($4 million round) - Fractional ownership of franchises (gyms, hair salons, car dealerships, etc
    • IMX Health ($5 million round) - Derivatives exchange for insurance providers, healthcare systems, and other healthcare participants to invest in tradable healthcare assets
  • Data
    • UrbanStat ($500,000 round) - Geospatial data for environmental disaster insurance underwriting.

3. Capital Markets Infrastructure: Novel mobile investment platforms offering access to a wider array of financial instruments and high-end trading tools, as well as API-driven services creating seamless integration between platforms and services, are seeing traction in the venture markets.

  • Architect ($12 million round) - allows users to trade US-regulated products with institutional-grade algorithms and portfolio management tools
  • Sarna Finance ($1 million round) - mobile investment platform to trade etfs, equities, options, and more
  • BridgeFT ($2 million round) - API first software connecting back office operations systems

Success Stories:

  • Amount - the platform helping banks and financial institutions digitize their retail product offerings founded in 2014 by Timothy Clarke, has raised over $300 million and was most recently valued at $1.1 billion in 2022.
  • M1 Finance - the personal finance management platform founded in 2015 by Brian Barnes has raised over $330 million to date and now oversees $10 billion in client assets.
  • Kin Insurance - minted as a unicorn in 2024 after raising a $15 million round, this DTC home insurance company founded by Sean Harper currently serves over 115,000 policyholders and manages $345 million of premium.
  • Clearcover - online car insurance platform founded by Kyle Nakatsuji in 2016 has raised hundreds of millions to date and ended 2023 with $168M in written premiums.

Joey Alfieri

Analyst, Venturing

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