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Clearcover Insurance

Digital car insurance with online management

Overview

Clearcover is a digital car insurance provider in the United States that uses automation and online platforms to offer affordable premiums and efficient coverage for modern drivers, including millennials and rideshare drivers. The product works through a primarily online experience: customers obtain and manage policies, file claims, and receive support via a mobile app and a web platform, while automated processes help control costs. This approach sets Clearcover apart from traditional insurers by concentrating on operational efficiency and digital management to pass savings to customers, rather than relying on a large network of bricks-and-mortar operations. The company’s goal is to deliver straightforward, cost-effective auto insurance with a convenient digital experience for policyholders.

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About Clearcover Insurance

Simplify's Rating
Why Clearcover Insurance is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Automotive & TransportationFintechFinancial Services

Company Size

51-200

Company Stage

Late Stage VC

Total Funding

$537.5M

Headquarters

Chicago, IL

Founded

2016

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What believers are saying

  • April 30, 2026 Florida launch adds fee-free pricing and planned state rollouts.
  • October 31, 2025 financing raised $25 million, supporting growth after $457 million total funding.
  • Ada and ServiceUp integrations cut support and repair cycle times, improving unit economics in 2026.

What critics are saying

  • Q2 2025 direct written premiums fell 18%; another slide triggers harsher 2026 capital dilution.
  • Timothy Milstead v. Clearcover Inc. entered ADR in 2026, extending employment-discrimination risk into 2027.
  • AI automation creates execution risk; a claims or underwriting failure destroys trust and regulatory goodwill.

What makes Clearcover Insurance unique

  • Clearcover runs AI-heavy claims and underwriting, with 90% claims intake automated by 2026.
  • Its 2025 CIX reciprocal exchange and CGA agency expand into non-standard auto markets.
  • The API-first stack integrates carriers, agents, and customers across digital quoting, claims, and service.

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Funding

Total Funding

$537.5M

Above

Industry Average

Funded Over

7 Rounds

Late VC funding comparison data is currently unavailable. We're working to provide this information soon!
Late VC Funding Comparison Coming Soon

Benefits

  • Medical, dental, & vision
  • Pre-tax benefits, disability, & life insurance
  • 401k with 3% match
  • Generous vacation
  • Parental leave
  • Equity
  • Employee resource groups
  • Top-of-the-line hardware

Growth & Insights and Company News

6 month growth

0%

1 year growth

2%

2 year growth

1%
Associated Press
Mar 5th, 2026
Clearcover launches Dearborn Labs to deploy production AI systems inside insurance carriers

Clearcover, an AI-native auto insurance carrier, has launched Dearborn Labs, a forward-deployed AI practice that builds and operates AI systems inside property and casualty insurance carriers and MGAs. Unlike traditional SaaS providers, Dearborn Labs embeds teams within client operations to deploy production systems within weeks. The practice is led by Kyle Nakatsuji, whose team at Clearcover achieved notable results: over 90% of claims intake runs through AI agents, 93% of policies are bound digitally, and claims handling operates at three times the efficiency of traditional carriers. Founded in 2026 as part of the Clearcover holding company, Dearborn Labs aims to help insurers integrate AI across underwriting, claims and operations. The firm is accepting a limited number of carrier and MGA engagements for Q2 2026.

Coverager
Nov 4th, 2025
Clearcover raises $25M in equity offering

Clearcover, a Chicago-based digital auto insurer, has filed an amended Form D with the SEC, revealing a $25 million equity securities sale. The filing, dated October 31, 2025, indicates an indefinite total offering amount with no broker-dealer fees. Founded in 2016, Clearcover has raised $457.2 million to date. In Q2 2025, it reported $63 million in direct written premiums, an 18% decrease from Q2 2024.

Coverager
Feb 13th, 2025
Clearcover Launches Reciprocal Insurance Exchange

Car insurance startup. Clearcover <i class="fa fa-info-circle company-popover" data-content="h3Clearcover/h3. div

Coverager
Jan 8th, 2025
Clearcover Launches Clearcover General Agency

Clearcover <i class="fa fa-info-circle company-popover" data-content="h3Clearcover/h3. div. table

PR Newswire
Aug 21st, 2024
Clearcover Drives Claims Efficiency By Partnering With Serviceup To Redefine Car Repair

The collaboration aims to provide a hassle-free repair experience for customersCHICAGO, Aug. 21, 2024 /PRNewswire/ -- Clearcover , a next-generation insurance company, announces a strategic partnership with ServiceUp , a leading technology company streamlining automotive repairs. The collaboration aims to redefine the car repair experience by combining Clearcover's seamless claims process with ServiceUp's exceptional "white glove" service and delivery.Through its mobile platform, Clearcover policyholders can now schedule and receive repairs and maintenance services without ever leaving their homes via ServiceUp's comprehensive vehicle repair solution, which provides pick up and delivery at the policyholder's location."We are thrilled to join forces with ServiceUp to bring an unmatched level of convenience and quality service to our customers," said Clearcover Chief of Claims and Customer Service Aaron Wheaton. "This tech-forward approach aligns with our commitment to innovation and customer satisfaction. We are already seeing improvements in efficiency."The benefits of the Clearcover partnership were recently highlighted in a Case Study published by ServiceUp. Results have shown repair process improvements for Clearcover, yielding impressive results, including reducing cycle times more than 30% and saving 20+ hours weekly per adjuster.ServiceUp CEO Brett Carlson said, "We're thrilled to partner with Clearcover to bring the power of ServiceUp's repair platform to its customers

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