Verifly Announces $22M Funding, Rebranding as Thimble

The funding was led by IAC, with participation from existing investors including Slow Ventures, AXA Venture Partners, and Open Ocean.

(Image source: Thimble website.)

Verifly, a distribution platform offering short-term liability insurance coverage for small businesses and independent workers, has announced Series A funding of $22 million and its rebranding as Thimble.  The funding was led by IAC, with participation from existing investors including Slow Ventures, AXA Venture Partners, and Open Ocean. Customers are able to get a quote, or purchase a policy and receive an instant Certificate of Insurance by visiting the website, or by using Thimble app available through the App Store or Google Play.

Jay Bregman, Co-founder and CEO, Thimble.

“We’ve reinvented insurance to make it simple, ​enabling small businesses ​to succeed on their own terms and take advantage of the flexibility and technology driving the modern economy,” comments Jay Bregman, co-founder and CEO, Thimble. “Recognizing a fundamental shift in the nature of modern work, Thimble broke the mold by introducing short-term micro-policies for purchase by the hour, day, week, month or year—all available in seconds via their app, web, and partner APIs.”

Thimble describes its offering as affordable, flexible, by-the-job coverage to fit the dynamic nature of small businesses in the gig economy. The firm says it offers insurance for more than 100 different occupations including handymen, landscapers, DJs, musicians, beauticians, and dog walkers.

“Thimble is just the kind of company IAC likes to back—a smart team with a disruptive technology that aims to shake up a traditional category,” comments Michelle Arbov, Head of M&A, IAC. “Jay and team are poised to redefine insurance coverage for the modern workforce. We’re excited to see what they can do.”

Michelle Arbov, Head of M&A, IAC.

Thimble sought to depart from the traditional model whereby liability policies were only available for annual purchase, which the company says poses a significant cost barrier for small businesses and sole proprietors, and leaving many uninsured and unable to accept jobs that require proof of insurance.

Thimble reports that it has been approved by regulators in 48 states. Policies are underwritten by Markel (Richmond, Va.).

Thimble reports that it has already sold over $100 billion in aggregate exposure and is on pace to sell 100,000 policies by year end to a market unserved by traditional insurers. The company says that 75 percent of its customers are new to business insurance altogether, which Thimble asserts shows its ability to capture the trust of small businesses unable or unwilling to buy into traditional annual policies. Thimble notes that 50 percent of the policies it sells cover a single day or less.

Breaking Down Barriers

Scott Whitehead, Managing Director, Markel.

“By breaking down barriers and leveraging technology, Thimble is doing more than bringing traditional policies online; it is leading the charge to better match insurance needs to the modern worker and delivering it in a way that will make insurance more like other industries,” comments Scott Whitehead, Managing Director, Markel. “The insurance industry generates over $100 billion of small business premium in the US alone, and that’s without the 40 percent of sole proprietors who do not currently purchase business insurance.”

Thimble says its rebrand from Verifly allows the company to expand from its roots as a pioneer of drone insurance to a full partner for all modern workers and small businesses as it grows in the on-demand economy. Thimble says it will be a partner not only for small businesses and workers who buy coverage directly through the app, but also for insurance brokers and independent agents as well who can use Thimble to provide short-term coverage options to clients with zero touch.

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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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