FinTech Summit
Jay BregmanThimble

Jay Bregman


Jay Bregman is the CEO & cofounder of Thimble, whose mission is to make insurance simple for businesses so they can succeed. Thimble’s on demand insurance was designed to provide a more flexible and affordable alternative to annual plans, with coverage by the hour, the day, or the month for businesses and their crew. Thimble has sold over 100,000 policies to small businesses all across America via its award-winning app, partner APIs, and broker tools. Thimble has raised $30M from investors including IAC.

Prior to Thimble, Jay founded Hailo, a ride-sharing company in London backed by marquee investors including Sir Richard Branson, and was acquired by Daimler (rebranded to FreeNow).



Thimble's mission is to make insurance simple, to help businesses succeed on their own terms. Thimble provides General and Professional Liability insurance via the industry’s first ondemand policies, in addition to monthly plans. Now, small businesses can get covered for as little as one hour or turn on coverage with simple monthly payments. Founded in 2016 by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised $30M in funding from IAC (NASDAQ: IAC) and other top firms. All Commercial General Liability policies are underwritten by Markel Insurance Company (NYSE: MKL). For more information, download the Thimble app or visit