Thimble Recognized as “Best for the Smallest Businesses” in’s 2020 Best Business Insurance List

The insurtech’s speed and breadth of coverage caught the attention of Money’s editors, along with its “cut the cord” approach to policy length

Thimble, the insurtech startup that helps small businesses succeed on their own terms, today was recognized on’s The Best Business Insurance of 2020 list. The award recognizes the best business insurance options of 2020 for those seeking financial protection for their organizations. 

Selected companies were evaluated on four major factors: range of coverage options, business types and sizes covered, and the ease of applying for a policy and submitting a claim. Thimble was recognized within the “Best for the Smallest Businesses” category, setting itself apart with its speed and breadth of coverage, offered hourly, daily, or monthly, along with its availability to over 100 types of small business professionals. Other major insurance companies on the list include Nationwide, Progressive and The Hartford.

The recognition follows a series of major innovations from the insurtech startup, including Thimble Monthly, which enables small businesses to “cut the cord” from annual policies via rolling monthly coverage; Thimble Pause, allowing businesses to place a hold on policies without penalty and without needing to cancel; and major partnerships with Hiscox and Angie’s List.

“We are thrilled that our contributions to the small business sector are receiving recognition, particularly among such great company in the business insurance space,” said Jay Bregman, CEO and Founder of Thimble. “Insurance is no longer a nice-to-have, it’s a must, particularly for small business owners facing extremely uncertain times. We strive to provide on-demand, instant, and flexible solutions in order to best meet business owners where their needs are at. This recognition is a testament to our ability to do just that.”

About Thimble

Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. Its flexible insurance policies are designed with small businesses in mind, who face great uncertainty in normal times, and are now on the road to economic recovery. Available by-the-month or for as little as one hour, Thimble coverage takes less than one minute to obtain and can be scaled up, adjusted or paused at any time. Thimble has sold over 100,000 policies representing over $125B in coverage since launching in 2016.

Founded by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised over $29 million in funding from IAC  and other top firms. All General Liability and Professional Liability policies are underwritten by Markel Insurance Company. For more information, visit



More from this Author