Clearcover

A JD/MA and Wisconsin native, Kyle was a founding member of American Family Insurance’s corporate venture arm. Kyle cut his teeth investing in IoT, SaaS and insuretech innovation before “insuretech” was even a thing. During his last several months at American Family Ventures, Kyle started to incubate something new and with AmFam’s blessing and financial support, Kyle left to start Clearcover with colleague, Derek Brigham.

The second theme that OMERS Ventures elected to pursue in the US was insuretech. One of the first calls that Michael made was to Kyle. Michael and Kyle had known each other from their respective prior lives. Clearcover wasn’t raising as Kyle had just completed a Series B a few months prior, but one thing led to another, and OMERS Ventures initiated a new financing process with Kyle culminating in a $50M Series C in December 2019.

Clearcover had a very specific strategy of using technology to enable a low-cost digital-centric personal auto insurance carrier. Starting as a managing general agent, Clearcover always intended to go full stack from both a risk-bearing and underwriting perspective as well as from an operational competency and tech stack perspective. The company’s gross written premiums have doubled less than a year into our investment and we’ve been proud to help Kyle make several key additions to his management team.