Jay Bregman

VP, Fundamental Underwriters at AF Group


Jay Bregman is the CEO & Cofounder of Thimble, insurance that helps small businesses succeed on their own terms. Thimble’s policies are designed for the uncertainty of starting, operating and growing a business–both in normal times and in times of heightened anxiety like 2020. As a result, Thimble has seen a surge in their monthly policies as customers opt to “cut the cord” in favor of insurance better-suited to the rapidly changing environment. 

Thimble has sold over 125,000 policies to small businesses all across America via its award-winning app, partner APIs, and broker tools, and has raised $30M from investors including IAC (NASDAQ: IAC).

Prior to Thimble, Jay founded Hailo, a ridesharing company in London backed by investors including Sir Richard Branson and acquired by Daimler. Earlier, he founded and sold eCourier, a technology-enabled services company to Royal Mail, the U.K. equivalent of USPS. Bregman holds a Master’s Degree from the London School of Economics and Political Science and a Bachelor’s Degree from Dartmouth College.