Thimble – #1 “Small and Mighty” startup on Fast’s 2021 list of the World’s Most Innovative Companies

The company has been recognized for its groundbreaking approach to insurance, at a time when small businesses need it most

NEW YORK (March 9, 2021) — Thimble, the insurtech that helps small businesses succeed on their own terms, ranks #1 overall in the “Small and Mighty” category on Fast Company’s 2021 list of the World’s Most Innovative Companies.

The award recognizes companies that, despite their size, are punching far above their weight class, making a significant impact in their respective industries. 

The Most Innovative Companies recognition comes after a momentous year for Thimble, marked by product announcements and partnerships designed to help small businesses cope with the challenges of operating in the pandemic. 

In February 2020, just before the first wave of lockdowns, Thimble launched its innovative Monthly product, which allowed customers to purchase insurance on a subscription basis. Thimble Monthly requires no deposits or cancellation fees, and alleviates the upfront financial burden that comes with purchasing inflexible annual coverage. 

In May, recognizing the strain that Main Street businesses were feeling from stay-at-home orders, Thimble announced the addition of its Pause feature, allowing business owners to put their coverage on hold at no cost via Thimble’s breakthrough app. This proved invaluable for small businesses dealing with unpredictable lockdowns and closures. 

Thimble also solidified relationships with major partners in the insurance and small business categories. In June, the insurtech announced a partnership with Angie’s List, which became the first to integrate Thimble’s API, making the startup’s on-demand policies accessible to its professionals with just a single touch. In the same month, Thimble announced a partnership with Hiscox, a global leader in small business insurance, to offer flexible coverage to its expansive pool of loyal customers. 

Additionally, in a move that underscored its commitment to helping small businesses in every possible way, Thimble announced a partnership with Lloyd’s of London to develop pandemic business interruption coverage. These policies will pay a sum programmatically if certain criteria are met–for example, if all companies in a certain zip code are forced to close–effectively providing an “instant stimulus” to the policyholder.

These partnerships are tangible proof that despite Thimble’s size, legacy companies are relying on its “small and mighty” mindset to innovate at a time when small businesses need it most.

“We’re honored to be recognized among many impressive companies on the Fast Company Most Innovative Companies list,” said Jay Bregman, CEO and Co-Founder of Thimble. “It’s certainly been a challenging year for us all, but I’m immensely proud of the Thimble team for all the hard work that helped us propel our growth in 2020. We’ve launched numerous new products to help small businesses, and we’re working with incredible partners to continue the positive momentum and aid in the recovery process.”

The World’s Most Innovative Companies is Fast Company’s signature franchise and one of its most highly anticipated editorial efforts of the year. It provides both a snapshot and a road map for the future of innovation across the most dynamic sectors of the economy. The full list of Most Innovative Companies can be viewed on Fast Company’s website.


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 via monthly subscription 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 $175B in insurance coverage since its inception.

Founded by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised over $30 million in funding from IAC, Open Ocean and other top firms. All General Liability and Professional Liability policies are underwritten by Markel Insurance Company. For more information, visit


Fast Company is the only media brand fully dedicated to the vital intersection of business, innovation, and design, engaging the most influential leaders, companies, and thinkers on the future of business. The editor-in-chief is Stephanie Mehta. Headquartered in New York City, Fast Company is published by Mansueto Ventures LLC, along with our sister publication Inc., and can be found online at


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