Thimble introduces monthly insurance plans for small businesses

The insurtech startup is helping SMBs “cut the cord” from static annual policies with month-to-month coverage that scales as they do.

New York (April 8, 2020) Thimble, the insurance partner that helps small businesses succeed on their own terms, is today introducing Thimble Monthly – a new form of insurance for small business owners who are ready to cut the cord from their annual policies.

Recognizing the shortcomings of annual insurance policies, Thimble Monthly is designed for established businesses that deserve a dynamic alternative that scales and adapts as they do. Thimble Monthly customers have full control of their policy via Thimble’s breakthrough insurance app, with the ability to 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.

“Most small businesses operate on razor-thin margins under normal circumstances. Given the current climate, businesses are now facing an unprecedented, unpredictable road, and we don’t know how long it will last,” said Jay Bregman, CEO and Founder of Thimble. “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 an incredible pace: it is currently available in 42 states and the District of Columbia, and already accounts for more than 30% of Thimble’s overall business. Perhaps more indicative of the product’s success with SMBs is that 33% of new customers switched from an annual insurance plan.

“I needed a general liability policy once we moved the company into a temporary studio space in San Diego. 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,” said Matt Alcobia, Founder and Executive Director of Noize Cartel, a record label for independent artists. “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 2019, Thimble became the first and only company to introduce On-Demand insurance, available by the hour, day or job, for America’s smallest businesses. Now, Thimble’s expansion into monthly insurance reflects its commitment to helping SMBs at various stages to grow and thrive on their own terms. To date, Thimble has resonated extremely well: The company averages 4.8 out of 5 stars on major review platforms, with an NPS score of 82, which is 3x higher than the industry average of 28.

In addition to targeting customers, Thimble’s 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% commission in perpetuity per new customer referred to any of its insurance products.

For more information on Thimble Monthly, visit

About Thimble

Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. Thimble provides General and Professional Liability insurance via the industry’s first on-demand and monthly policies. Small businesses can get covered for as little as one hour or turn on coverage with simple monthly payments. Founded in 2016 by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised over $29 million in funding from IAC (NASDAQ: IAC) and other top firms. All Commercial General Liability policies are underwritten by Markel Insurance Company (NYSE: MKL). For more information, download the Thimble app or visit

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