Newly-rebranded Thimble raises $22M to bring flexible insurance to the gig economy

Thimble, which offers flexible, short-term insurance to small businesses and freelancers, is announcing that it has raised $22 million in a Series A funding round led by IAC.

Until today, the startup was known as Verifly, a name tied to the company’s initial aim of providing insurance to drone pilots. However, founder and CEO Jay Bregman (who previously founded ridesharing company Hailo) said that thanks to customer demand, the team kept adding insurance for different types of businesses — and now it’s rebranding to reflect that broader vision.

While it’s easy to talk about Thimble customers as being part of the “gig economy,” Bregman noted that these aren’t just people driving for Uber or delivering for Postmates — only 4% of the company’s customers identify as gig economy workers.

“There is this larger thing called the gig economy: People working in flexible ways, on their own terms,” he said.

In fact, Thimble now says it provides liability coverage for customers in more than 100 professions, including handymen, landscapers, DJs, musicians, beauticians and dog walkers. Policies can be purchased directly from the Thimble website or app by the hour, day, week, month or year.

The idea, Bregman said, is that

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