Clearcover

Clearcover is a digital personal auto insurance company headquartered in Chicago, Illinois, founded in 2016 by Kyle Nakatsuji and Derek Brigham to sell car insurance directly online through an API-first platform. Its consumer proposition centers on a mobile app through which drivers can obtain quotes, select coverages and file claims; the company states that its claims technology can assess eligibility and issue payment on qualifying claims in minutes, citing a record payment of seven minutes on 28 January 2021 and noting that most claims are paid in under a week.

Standard policies include liability coverage (bodily injury and property damage), comprehensive and collision, uninsured/underinsured motorist bodily injury, medical payments/personal injury protection, roadside assistance and rideshare add-ons, and an alternate transportation coverage that pays cash the policyholder can spend on any form of transportation rather than reimbursing only a rental car. The site also offers a self-serve "60-Second Coverage Wizard" that guides prospective customers through coverage selection.

Underwriting is carried out through several entities: Clearcover Insurance Company, the Clearcover Inter-Insurance Exchange (CIX), a reciprocal exchange launched in Illinois in 2025, and Clearcover General Agency (CGA), a managing general agency launched in Texas in 2025 to serve the non-standard auto market with policies underwritten by Old American County Mutual Fire Insurance Company.

Founding story

Kyle Nakatsuji and Derek Brigham founded Clearcover in Chicago in 2016 with the aim of building an auto insurer that could quote and bind policies entirely online without a network of agents, an approach that shaped its API tooling and later insurance products. The co-founders lived in different cities when they formed and launched the company.

Business model

Clearcover sells personal auto insurance directly to consumers online and through independent agents, and distributes via embedded and API integrations with partner platforms such as comparison and marketplace sites. Risk is carried and administered through multiple underwriting vehicles — its own insurance company, a reciprocal exchange (CIX) and a general agency (CGA) writing non-standard auto business underwritten by a third-party carrier.

Revenue derives from personal auto insurance premiums written through its underwriting entities, and from fee-based agency arrangements where policies are underwritten by a partner carrier (CGA business underwritten by Old American County Mutual Fire Insurance Company).

Traction

The company reports a record eligible-claim payment of seven minutes (28 January 2021) with most claims paid in under a week. Its team tripled in size between March 2020 and July 2022, with employees in 30 states. It was ranked No. 56 on Deloitte's 2023 Technology Fast 500 and has been named to insurtech and fastest-growing private company lists by Forbes, CNBC, Inc. and Deloitte. In June 2024 CEO Kyle Nakatsuji described the company as "well on the path to profitability" as auto market conditions rebounded.

Latest developments

In February 2025 Clearcover launched the Clearcover Inter-Insurance Exchange, a reciprocal insurance exchange beginning in Illinois, to expand in non-standard auto. In January 2025 it launched Clearcover General Agency, an MGA serving the Texas non-standard auto market with policies underwritten by Old American County Mutual Fire Insurance Company, and announced a partnership with Claim Genius for AI-driven damage assessment and claim estimation. During 2024 it partnered with ServiceUp on vehicle repairs and with Ada on a generative-AI customer service assistant, launched a generative AI tool to digitize statement collection in claims, and disclosed plans to capitalize the new reciprocal with funds on hand.