Insurtech: Chicago-based Clearcover, a Car Insurance Provider, Finalizes $50 Million Series C Round

Chicago-headquartered Clearcover, a company focused on improving the way people acquire car insurance, has completed its third investment round.

Clearcover revealed on January 3 that it had finalized a $50 million Series C round, which was led by OMERS Ventures. Existing investors American Family Ventures, Cox Enterprises and IA Capital Group also took part in the firm’s latest funding round.

Michael Yang, managing partner at OMERS Ventures, will be taking a seat on Clearcover’s board of directors, the company confirmed.

The recent funding round has come after Clearcover secured $43 million through a Series B round in January 2019. The completion of the latest round brings the firm’s total capital raised to over $104 million since it was established in 2016. Clearcover managed to raise $11.5 million in 2017.

Established by company CEO Kyle Nakatsuji, a former VC at American Family Insurance, Clearcover has developed a platform that makes automobile insurance coverage more affordable by reducing the cost of operations, marketing and distribution, and then passing the savings to clients by offering economical, higher-quality vehicle insurance packages and products.

Last year, Clearcover’s management revealed that it had tripled its total policy sales year-over-year. Clearcover also raised funding via its Series B round last year. At the time, the company was only providing its services in California. But in only a year, Clearcover has expanded its operations to Arizona, Illinois, Ohio and Utah.

Clearcover’s management states that it’s planning to use the funds raised to continue developing its insurance technology (Insurtech) products and also to introduce its services in new markets and states across the US.

A greater number of people are now becoming used to filing claims and finding insurance packages online or digitally. In fact, around 90% of Clearcover’s policyholders use the company’s app, which the firm reveals is “substantially higher than the rest of the industry.” Approximately 60% of its clients are able to file claims digitally via its app.



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Oct 22, 2026 vs Jan 1, 2025 - Oct 22, 2025

Share this graph
Number of Filings130Prior 125 +4.0%
Target Raise, Total$3.37BPrior $3.54B -4.7%
This YTDYear priorChange
Filings 130 125 +4.0%
Target raise $3.37B $3.54B -4.7%

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Source: DisclosureQuest. Initial Form 1-A only.

Created by Crowded Media Group

This display counts initial Form 1-A filings only. It does not represent subsequent filings, including Form 1-A/A amendments or Form 1-A POS post-qualification updates filed by the issuer. Amounts are the stated Amount to be Raised on the initial filing, not capital raised and not amounts revised in later filings.

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