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Essential risk protection
by the hour, day, or month.


New York





Thimble is a mobile on-demand insurance platform. The company enables small businesses to “tap a button, get insurance.” They do this by marrying proprietary technology with specialized episodic insurance products. Our policies and ratings are built from scratch and approved by regulators to support an on-demand, pay-as-you-go experience when buying anytime from an hour to months of cover.

Thimble was founded in 2015 and has raised $3.8mm. Thimble, based in NYC, was founded by Jay Bregman, founder of Hailo, in which Sir Richard Branson was an investor (and sold to Daimler Mercedes-Benz) and Eugene Hertz, founder of Quidsi (sold to Amazon for $545mm). The combined annual revenue of businesses started by our founders exceeds $1B.

Thimble’s first product was an episodic aviation liability policy for commercial drone operator small businesses. Policies are purchased geographically and the rating system dynamically adjusts the hourly premium based on local conditions and risks (e.g. airports). The system is the market leader in drone insurance with over $10B in risk covered in less than a year and over 12,000 policies sold. It has also earned Thimble a reputation with regulators who have admitted its episodic policy in 49 states.

Thimble policies are designed to be distributed through software. They have an app to purchase and manage policies (issue certificates, add additional insureds, etc) as well as an API which enables integration into partner platforms. They cater to the mobile-first customer who is running their business largely on their phone. The policies give customers choice – to purchase as little as an hour or as long as twelve months – with everything in between. In addition, customers in seasonable businesses or who know they will only require insurance when working in a particular trade each Monday may purchase insurance to suit their schedule.


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