- Clearcover Insurance Company, founded in 2016 and headquartered in Chicago, operates as a digital-first auto insurance provider, reporting $123 million in written premiums for 2025, a 14.5% decrease from the previous year.
- In March 2026, Clearcover launched Dearborn Labs to deploy customized AI systems within insurance operations and selected Strada to automate customer-facing operations, achieving a 74% resolution rate and a 24-point increase in customer satisfaction.
- Clearcover has raised a total of $457.2 million in funding from notable investors including Lightbank, OMERS, and Cox Enterprises, positioning itself as a significant player in the insurtech space.
- Ideal buyers for Clearcover include property and casualty insurance carriers looking to enhance operational efficiency and customer service through AI-driven solutions, addressing the need for integrated and scalable technology in a rapidly evolving market.
Clearcover’s largest groups are Finance & Administration (36 employees, 19% of total headcount) and Engineering (35 employees, 19%). Sales & Support follows closely with 33 employees, while Business Management contributes 31 team members who oversee strategy, legal, and compliance functions. Marketing & Product collectively account for 20 employees, supporting brand awareness and feature rollouts. An additional 30 employees fall under the “Other” category, covering specialized roles that do not fit traditional departments. Smaller units such as Quality round out the organizational chart with focused expertise.
Clearcover operates with a distributed workforce anchored in Chicago, which hosts 55 employees and functions as the primary hub for leadership, engineering, and operations. Remote and hybrid roles are prominent; 97 employees work from various “Other” locations across the United States. Secondary office presences include Detroit (8 employees), Dallas (5), New York City (5), Phoenix (4), San Francisco (4), Atlanta (4), Tampa (2), and Jacksonville (2). This wide geographic spread enables Clearcover to access diverse talent pools while remaining close to major insurance and fintech markets.
