Thimble Introduces Monthly Insurance Plans for Small Businesses  

Customers can buy a policy within 60 seconds, and using the Thimble Monthly app can scale coverage, add insureds or switch plans instantly.

(Image source: Thimble homepage.)

Thimble, a startup insurance distributor providing hourly policies for smaller SMBs and gig workers, has introduced Thimble Monthly, an alternative to annual coverage for any SMB’s needing insurance for a period less than a year.

Recognizing the shortcomings of annual insurance policies, Thimble Monthly is designed for established businesses that deserve a dynamic alternative that grows and adapts as they do, according to a Thimble statement. Customers using the Thimble Monthly app can scale coverage, add insureds or switch plans instantly. Thimble Monthly can be purchased in just 60 seconds, requires no upfront fees or deposits, and delivers proof of insurance immediately via mobile or web, the statement says.

Jay Bregman, Founder and CEO, Thimble.

“Most small businesses operate on razor-thin margins under normal circumstances,” comments Jay Bregman, founder and CEO, Thimble. “Given the current climate, businesses are now facing an unprecedented, unpredictable road, and we don’t know how long it will last. We built Thimble Monthly to put control of the insurance policy into the hands of the business owner. Our many conversations with small business owners underscored the massive disconnect between existing insurers and reality. Now more than ever, this flexibility will be vital as SMBs look forward and adapt.”

Since soft-launching in February, Thimble Monthly has grown at a rapid pace, according to Thimble. The offering is currently available in 48 states and the District of Columbia, and already accounts for more than 30 percent of Thimble’s overall business. Thimble reports that 33 percent of its new customers switched from an annual insurance plan.

Buying Only the Coverage Needed

“I needed a general liability policy once we moved the company into a temporary studio space in San Diego,” comments Matt Alcobia, Founder and Executive Director of Noize Cartel, a record label for independent artists. “We’re only there for six months, so I was looking for a short-term quote. No one would quote me for anything less than a year. The cheapest quote I got outside of Thimble was $700 with the full premium paid upfront. I ended up taking out a Thimble policy right then and there and got a certificate of insurance instantly. We bought only the coverage we needed, and everything was really smooth and easy.”

In addition to targeting customers, Thimble says its Monthly product is immediately available to its network of over 2,000 broker partners in search of affordable and flexible options for their clients. The company will continue to offer all brokers $50 and 10 percent commission in perpetuity per new customer referred to any of its insurance products. Thimble says that in its interaction with consumers, it averages 4.8 out of 5 stars on major review platforms, with an NPS score of 82, which is three times higher than the industry average of 28.

All of Thimble’s Commercial General Liability policies are underwritten by Markel Insurance Company (Glen Allen, Va.). Its Aviation Liability (drone) policies are underwritten by Global Aerospace, Inc. (London) and backed by its pool of insurance companies.

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Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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