Jay Bregman is a serial entrepreneur and currently the cofounder and CEO of Thimble which is an insurance producer enabling small businesses to succeed on their own terms. The company has raised $30 million from Slow Ventures, LocalGlobe, Frontline Ventures, AXA Venture Partners, OpenOcean, Novel TMT Ventures, ValueStream Ventures, and IAC to name a few. Prior to this, he cofounded Hailo (acquired by Daimler Mercedes-Benz) and eCourier (acquired by Royal Mail).