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- Clearcover
Clearcover Valuation, Funding & Investors
Clearcover is valued at $1B as of October 2025.
Last Clearcover valuation
$1B
Undisclosed stage · Oct 2025
Last Clearcover funding round
$25M
Undisclosed stage · Oct 2025
Cumulative funding Clearcover raised
$457M
across 8 funding rounds
Key investors in Clearcover
American Family Ventures
Cox Enterprises
IA Capital Group
Silicon Valley Bank
Comcast Ventures
OMERS Ventures
About Clearcover
Clearcover is a Chicago-based digital auto insurer founded in 2016 by Kyle Nakatsuji and Derek Brigham, former American Family Insurance employees. The company sells online auto insurance built around fast claims processing, transparent pricing, and an app-based customer experience, and has since added embedded insurance partnerships and AI-driven claims automation. Clearcover has also developed its own reciprocal insurance entity to expand into non-standard auto risks beyond its core direct-to-consumer product.
Founded
2016
HQ
Website
Status
Privately held
Customer focus
B2C
Revenue model
Product sales
Valuation
$1B (Oct 2025)
Clearcover Valuation
Clearcover is currently valued at $1B, based on its undisclosed-stage round in October 2025.
Clearcover's valuation has moved from $1B at its Series D in April 2021 to $1B in October 2025, across 2 priced rounds.
Clearcover valuation by funding round
| Date | Stage | Valuation |
|---|---|---|
| Oct 2025 | Undisclosed stage | $1B |
| Apr 2021 | Series D | $1B |
Clearcover Funding History
Clearcover has raised a total of $457M across 8 funding rounds.
Clearcover's first fundraising round was a $3M seed round in November 2016. The most recent completed round was a $25M undisclosed-stage round in October 2025.
Clearcover funding rounds
| Date | Stage | Investors | Raised | Valuation | Deal Summary |
|---|---|---|---|---|---|
| Oct 2025 | Undisclosed stage | - | $25M | $1B | Clearcover is a Chicago-based digital auto insurance platform founded in 2016 by Kyle Nakatsuji and Derek Brigham, former American Family Insurance employees. The company offers online auto insurance with faster claims processing, transparent pricing, and an intuitive digital experience. Clearcover became a unicorn in April 2021 after raising a $200 million Series D round led by Eldridge Industries at a $1 billion post-money valuation. The company has since expanded its product offerings, launching embedded insurance solutions with partners like Experian and developing its own reciprocal insurance entity to expand into non-standard risks. In October 2025, Clearcover raised an additional $25 million in a Series E funding round focused on expanding AI-driven claims processing and automation capabilities. As of the most recent disclosures, Clearcover had raised over $610 million cumulatively across 13 funding rounds and employed 201-500 people, maintaining its position as a leading insurtech platform and appearing on CNBC's list of the world's top 150 insurtech companies. |
| Nov 2024 | Undisclosed stage | - | $70M | - | Clearcover is a Chicago-based digital auto insurer founded in 2016, offering an online platform with AI-driven claims processing, transparent pricing, and fast customer service to compete in the insurtech space. Competitive context includes peers like Root Insurance and Lemonade, with Clearcover emphasizing digital transformation accelerated by COVID-19, nationwide expansion, and product investments. The company has raised over $450-520 million across multiple rounds, including a $50M Series C in early 2020, $200M Series D in April 2021 led by Eldridge Industries valuing it at $1B unicorn status, and later extensions like $44M in November 2024 and $25M in October/November 2025. Total funding varies across sources from $329.5M to $520M, with investors including Omers Ventures, American Family Ventures, Cox Enterprises, and Eldridge. In 2020, Clearcover reported an annual run rate of nearly $70M, up 4x year-over-year, amid expansion to multiple states and team growth from 44 to 130 employees. Recent activities include embedded insurance strategies with partners like Experian, filings for amended securities offerings, and recognition on lists like Inc. 5000 and Deloitte Technology Fast 500. |
| Apr 2024 | Undisclosed stage | - | $55M | - | Clearcover is a Chicago-based insurtech company founded in 2016, offering a digital platform for auto insurance with faster claims processing, transparent pricing, and AI-driven features. The company has raised significant funding historically, including a $200M Series D round in April 2021 led by Eldridge Industries that valued it at $1B, bringing total funding to around $457M as of later reports. It operates in multiple U.S. states, focusing on digital transformation in insurance accelerated by the COVID-19 pandemic. Around November 2024, Clearcover filed for a $44M funding round. A later $25M Series D extension occurred on 04.11.2025 (likely November 4, 2025), aimed at expanding AI-driven claims processing and partnerships. Historical traction includes expansion to 25 states by end-2021, 450 employees as of late 2021, and total funding exceeding $480M-$520M in company press mentions, with recognition on lists like Inc. 5000 and Deloitte Technology Fast 500. The company plans growth into non-standard risks and embedded insurance strategies. Competitive context includes other insurtechs like Lemonade achieving ARR milestones, while Clearcover emphasizes technology for cost reduction and customer targeting. Investors have included Eldridge Industries, American Family Ventures, Cox Enterprises, OMERS Ventures, University Growth Fund, and Geodesic Capital. Recent developments involve launching reciprocal structures and partnerships like with Experian for embedded quotes. |
| Apr 2021 | Series D | Eldridge Industries (lead); Sixty Degree Capital; R136 Ventures; American Family Ventures; HPA (Hyde Park Angels); Comcast Ventures; Cox Enterprises; Geodesic Capital; OMERS Ventures; IA Capital Group | $200M | $1B | Clearcover, a Chicago-based insurtech startup founded in 2016, provides digital car insurance with a technology-first platform offering fast, affordable coverage through an API-based approach, targeting modern drivers seeking streamlined experiences and lower prices compared to legacy insurers. On April 13, 2021, it closed a $200 million Series D funding round led by Eldridge Industries, with participation from American Family Ventures, Cox Enterprises, OMERS Ventures, Hyde Park Angels, and other new investors including Comcast Ventures, Geodesic Capital, IA Capital Group, R136 Ventures, and Sixty Degree Capital, bringing total funding to $329 million. The round valued Clearcover at $1 billion, positioning it as a unicorn in the accelerating digital transformation of the auto insurance industry. The new capital was earmarked to accelerate innovation in digital insurance offerings, expand into additional markets—having already launched in 15 states including Arizona, California, Georgia, Illinois, Indiana, Louisiana, Maryland, Missouri, Nebraska, Ohio, Oklahoma, Pennsylvania, Texas, Utah, and Wisconsin—and double overall headcount by investing in insurance, product, and engineering teams. Clearcover emphasized its mission to deliver better value for less money amid industry shifts from analog to digital models. CEO Kyle Nakatsuji highlighted the focus on customizable options and nationwide growth, while Eldridge's Todd Boehly praised the company's scalability and competitive product. This Series D followed prior rounds including a $50 million Series C in January 2020 led by OMERS Ventures and earlier raises totaling over $100 million previously. The funding came after a strong 2020 with state expansions and C-suite additions like CFO Norman Smagley and Chief Insurance Officer Vandana Venkat. Clearcover continued growth post-round, with later developments including additional funding in 2025 and embedded insurance strategies. |
| Jan 2020 | Series C | OMERS Ventures (lead); American Family Ventures; Comcast Ventures; Cox Enterprises; IA Capital Group | $50M | - | Clearcover is a Chicago-based digital auto insurance company founded in 2016 that uses technology to provide faster, hassle-free car insurance quotes and claims processing, aiming to offer better coverage at lower prices to U.S. drivers. The company closed a $50 million Series C funding round on January 3, 2020, led by OMERS Ventures, with participation from existing investors American Family Ventures, Cox Enterprises, and IA Capital Group. This brought total funding to over $104 million following a $43 million Series B in January 2019 and earlier rounds. Michael Yang from OMERS Ventures joined the board to support scaling and geographic expansion. The funds were intended to fuel Clearcover's growth, including expanding its availability to more of the 230 million licensed U.S. drivers, enhancing its technology platform, and accelerating market presence amid a shift toward digital insurance models. Clearcover positioned itself as a disruptor in the legacy auto insurance industry by leveraging AI and modern customer experience design for competitive advantages. Later rounds included a $200 million Series D in April 2021 led by Eldridge, reportedly valuing the company at $1 billion or more, and subsequent raises bringing total funding over $300 million by 2025. |
| Jan 2019 | Series B | Cox Enterprises (lead); Lightbank; American Family Ventures; HPA (Hyde Park Angels); Connor Theilmann; Silicon Valley Bank; IA Capital Group | $43M | - | Clearcover, a Chicago-based insurtech startup founded in 2016, provides technology-driven car insurance through an industry-first API platform that streamlines purchasing, reduces costs by bypassing traditional marketing, and offers savings of up to 50% for customers. Launched in California in early 2018, the company had sold thousands of policies, integrated with partners like Cars.com, The Zebra, and Chime, and enabled drivers to save millions on insurance by the time of its Series B announcement. On January 22, 2019, Clearcover raised $43 million in a Series B round led by Cox Enterprises, with participation from American Family Ventures, IA Capital Group, Lightbank, Hyde Park Angels, and debt financing from Silicon Valley Bank. This followed a $11.5 million Series A in 2017 led by Lightbank. Proceeds were allocated to expand into about half a dozen new states including Illinois and Georgia, enhance the API platform, integrate additional distribution partners, and hire over 50 employees in engineering, data science, and customer advocate roles. CEO Kyle Nakatsuji highlighted the customer-focused model resonating in the market, while Cox's Spencer Boice noted Clearcover's potential in the $231-250 billion U.S. auto insurance industry through data and digital innovation. Clearcover differentiated by focusing on cost structure via technology rather than repricing products, enabling aggressive state expansion and partnerships across automotive, insurance, and fintech sectors. |
| Sep 2017 | Series A | Lightbank (lead); Greycroft; Silicon Valley Bank; 500 Global | $12M | - | Clearcover is a Chicago-based car insurance technology company founded in 2016 by former American Family Insurance employees Kyle Nakatsuji and Derek Brigham. The company developed an API-based insurance platform using data-driven technology and artificial intelligence to streamline car insurance purchasing and reduce costs, claiming to save customers up to 50% compared to traditional carriers by eliminating excessive marketing and outdated operational processes. In September 2017, Clearcover exited stealth mode and announced its initial funding round of $11.5 million, led by Lightbank with participation from Greycroft Partners, 500 Startups, Silicon Valley Bank, and other insurance and fintech investors. The company intended to use the funding to scale partnerships and launch its car insurance product, which would be available through partner channels and directly on its website. The platform was designed to make custom coverage recommendations using artificial intelligence and eliminate unnecessary overhead costs that traditional carriers pass to consumers. Clearcover's distribution model focused on API-based integrations at high-relevance moments in the customer journey, differentiating it from traditional direct-to-consumer or agent-based insurance sales. The company positioned itself against the industry's $50 billion annual spend on marketing, agency infrastructure, and outdated processes, targeting efficiency gains that could enable lower pricing for comparable coverage quality. |
| Nov 2016 | Seed | - | $3M | - | Clearcover is a Chicago-based insurtech company founded in 2016 that provides a digital platform for auto insurance with faster claims processing, transparent pricing, and AI-driven custom coverage recommendations. The company offers an intuitive online experience to help customers save money on car insurance. Clearcover's early funding history includes a round on September 22, 2017, raising $11.5 million, bringing total funding at that time to around $54.5 million after a prior round led by Cox Enterprises. This was described as the company's second round of funding. A subsequent Series B round occurred on January 22, 2019, raising $43 million. Later rounds include a Series C on January 3, 2020, raising $50 million led by OMERS Ventures, increasing total funding to over $104 million, and a Series D on April 16, 2021, raising $200 million at a $1 billion valuation led by Eldridge Industries. The company continued raising capital with additional rounds in 2025, reaching total funding of approximately $457 million. |
Who has invested in Clearcover?
15 investors have backed Clearcover across its funding rounds, including American Family Ventures, Cox Enterprises, IA Capital Group, Silicon Valley Bank, Comcast Ventures and OMERS Ventures.
Lead investors include Eldridge Industries, OMERS Ventures, Cox Enterprises and Lightbank.
Clearcover Investors
| Investor | HQ | Rounds | Role | First check |
|---|---|---|---|---|
| 3 | Participant | Jan 2019 | ||
| 3 | Lead | Jan 2019 | ||
| 3 | Participant | Jan 2019 | ||
| 2 | Lead | Sep 2017 | ||
| 2 | Participant | Jan 2019 | ||
| 2 | Participant | Jan 2020 | ||
| 2 | Lead | Jan 2020 | ||
| 2 | Participant | Sep 2017 | ||
| 1 | Participant | Apr 2021 | ||
| 1 | Participant | Apr 2021 | ||
| 1 | Participant | Sep 2017 | ||
| 1 | Participant | Apr 2021 | ||
| 1 | Participant | Jan 2019 | ||
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Start Free TrialClearcover Competitors
Clearcover competitors include listed companies like Trupanion and Hippo Insurance, and private ones like Acko, Sidecar Health, Branch and Ladder.
| Company | HQ | Status | Revenue | EBITDA | Valuation | Revenue Multiple |
|---|---|---|---|---|---|---|
| Private | $303M | - | $1B | 3.3x | ||
| Private | - | - | $1B | - | ||
| Private | - | - | $1.1B | - | ||
| Private | - | - | $900M | - | ||
| Publicly listed | $1.4B | $39M | $1.1B | 0.5x | ||
| Publicly listed | $469M | $84M | $844M | 1.2x |
Clearcover Public Comps
Clearcover is still privately-owned, but its public comps include Sagicor Group Jamaica, Anadolu Hayat Emeklilik, Helia Group, Heritage Insurance, International General Insurance, Anadolu Sigorta, John Hancock, Capricorn Group, Chesnara and AgeSA.
| Last FY | EV/Revenue | EV/EBITDA | ||||||
|---|---|---|---|---|---|---|---|---|
| Revenue | EBITDA | Last FY | LTM | 2027E | Last FY | LTM | 2027E | |
| $558M | $153M | 1.8x | - | 6.7x | - | |||
| $769M | $170M | 1.1x | 1.5x | 4.9x | - | |||
| $288M | $268M | 3.5x | 4.7x | 3.7x | - | |||
| $774M | $282M | 0.7x | 0.6x | 2.0x | - | |||
| $525M | $131M | 1.7x | 1.8x | 6.7x | - | |||
| $1.9B | $361M | 0.2x | 0.1x | 0.8x | - | |||
| $106M | - | 12.5x | - | - | - | |||
| $342M | - | 2.6x | - | - | - | |||
This data is available for Pro users. Sign up to see all Clearcover competitors and their valuation data. Start Free Trial | ||||||||
Common questions about Clearcover
| When was Clearcover founded? | Clearcover was founded in 2016. |
| Where is Clearcover headquartered? | Clearcover is headquartered in United States. |
| Is Clearcover publicly listed? | No, Clearcover is a private, VC-backed company. |
| What is Clearcover's valuation? | Clearcover was last valued at $1B in its undisclosed-stage round in October 2025. |
| How much funding has Clearcover raised? | Clearcover has raised $457M across 8 funding rounds. |
| What was Clearcover's last funding round? | Clearcover's last funding round was a $25M undisclosed-stage round in October 2025. |
| Who are Clearcover's investors? | Clearcover's investors include American Family Ventures, Cox Enterprises, IA Capital Group, Lightbank, HPA (Hyde Park Angels), Comcast Ventures, OMERS Ventures, Silicon Valley Bank, Sixty Degree Capital, R136 Ventures and 5 others. |
| Which companies are comparable to Clearcover? | Companies comparable to Clearcover include Acko, Sidecar Health, Branch, Ladder, Trupanion and Hippo Insurance. |
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