IAC Leads $22 Million Funding in Newly Branded Thimble

NEW YORK — Verifly, which offers short-term liability coverage for small businesses and independent workers, is changing its name to Thimble, and has also raised $22 million in Series A funding. The funding was led by NY Internet conglomerate IAC, with participation from existing investors including Slow Ventures, AXA Venture Partners, and Open Ocean.

“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,” said Thimble co-founder and CEO Jay Bregman. 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 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,” said 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.”

Thimble offers affordable, flexible, by-the-job coverage to fit the dynamic nature of small businesses in the gig economy. Insurance is available for more than 100 different professions including handymen, landscapers, DJs, musicians, beauticians, and dog walkers.

Previously, liability policies were only available for annual purchase, posing 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 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. In fact, 75% of Thimble’s customers are new to business insurance altogether, showing the company’s ability to capture the trust of small businesses unable or unwilling to buy into traditional annual policies. 50% of Thimble policies sold cover a single day or less.

“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,” said Scott Whitehead, Managing Director of 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.”