Thimble (formerly Verifly) provides flexible, short-term liability insurance that can be purchased by the hour, day, week, month or year. The product targets a broad set of independent workers and small businesses, offering coverage for more than 100 professions including handymen, landscapers, DJs, musicians, beauticians and dog walkers. The company says 75% of its customers were previously uninsured and that 50% buy policies covering a single day or less; it is on track to sell 100,000 policies by the end of the year. Thimble’s policies are underwritten by Markel, while Thimble retains ownership of the product and works with carrier partners to bring offerings to market. The business rebranded from Verifly after expanding beyond its original focus on drone pilots; founder and CEO Jay Bregman previously founded ridesharing company Hailo. Thimble has regulatory approval to sell insurance in 48 states and positions itself to serve workers doing flexible, transactional work even though only 4% of its customers identify as gig economy workers.

Total raised

$22M

Funding rounds

1

Latest round

Series A

Latest activity

Oct 2019