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).