Clearcover

Clearcover is a digital auto insurance company based in Chicago, Illinois. Kyle Nakatsuji and Derek Brigham founded the company in 2016 to sell car insurance directly online through an API-first platform. The insurer built its business around fast claims handling and a technology-driven approach to underwriting.

Website: clearcover.com

Head office address: 33 W Monroe Street, Suite 1750, Chicago, Illinois 60603

Founded: 2016, Chicago, Illinois

Founders: Kyle Nakatsuji and Derek Brigham

Company type: privately held; underwritten through Clearcover Insurance Company, Clearcover Inter-Insurance Exchange (CIX), and Clearcover General Agency (CGA)

Business focus: digital personal auto insurance

Regions served: multiple states across the US

History of Clearcover

Nakatsuji and Brigham wanted to build an auto insurer that could quote and bind policies online, without a network of agents. That approach shaped every stage of the company’s growth, from its first API tools to its later insurance products.

• 2016: Kyle Nakatsuji and Derek Brigham found the company in Chicago and launch its first direct-to-consumer auto policies
• 2018: the insurer expands its API program, letting partners such as auto marketplaces and comparison sites embed its quotes on their own platforms
• 2020: the company closes a $50 million Series C funding round led by OMERS Ventures to fund its underwriting technology and state expansion
• 2021: it raises $200 million in a round led by Eldridge, its largest single funding round at the time
• 2025: the company launches CGA in Texas, its entry into non-standard auto insurance, with policies underwritten by Old American County Mutual Fire Insurance Company
• 2025: it also launches CIX, a reciprocal exchange that begins operating in Illinois

These additions turned the company from a single-carrier startup into a group of underwriting entities that reach a wider range of drivers.

What does Clearcover insure?

The company focuses on personal auto insurance, sold directly online and through independent agents. Its standard policies cover the usual state requirements, along with a handful of add-ons drivers can choose individually.

• liability coverage for bodily injury and property damage
• comprehensive and collision coverage for damage to a driver’s own vehicle
• alternative transportation coverage, a cash payout drivers can use for a rental car, rideshare, or other transportation while a vehicle is repaired
• roadside assistance and rideshare coverage as optional add-ons
• non-standard auto policies, offered through CGA, for drivers who don’t qualify for standard coverage

The insurer’s standard and non-standard lines let it reach more types of drivers than a single-carrier competitor typically can.

Market position

The company competes in a crowded direct-to-consumer auto insurance space alongside other digital carriers. The firm’s structure sets it apart. The company operates through several underwriting entities instead of one single insurance carrier. These include its own insurance company, a reciprocal exchange, and a general agency for non-standard risks.

The firm says this setup gives it more flexibility to write business across different types of drivers and states. Forbes and CNBC have both named Clearcover to lists covering insurtech and insurance companies. Inc. and Deloitte have also ranked it among the country’s fastest-growing private companies.

Check the news section below for Clearcover’s latest updates and coverage.