Thimble
7 known investors
Thimble is a US insurtech selling on-demand liability insurance to small businesses and independent workers by the hour, day, week or month.
Also known as Thimble Insurance · Verifly
Investors · 7
Also in the syndicate · 2
Company profile
researched Aug 2026Thimble is a technology-driven insurance producer offering liability coverage to small businesses, independent workers and freelancers in the United States. Policies are purchased through the company's website or its proprietary smartphone app and can be bought in flexible increments covering an hour, a day, a week, a month or a year, rather than only on a standard annual basis. Coverage at the time of the company's 2019 Series A announcement was underwritten by Markel.
The company was founded in 2016 as Verifly, initially selling insurance to drone pilots, and later broadened its product set to serve a wider range of small businesses. It rebranded to Thimble in October 2019 alongside its Series A financing, with founder and CEO Jay Bregman describing the new name as reflecting an addressable opportunity spanning every type of small business rather than a single vertical. By late 2019 Thimble offered liability coverage across more than 100 professions, including beauticians, DJs, dog walkers, handymen, landscapers and musicians.
Founding story
Jay Bregman, a serial founder previously behind the London-based same-day courier company eCourier (acquired by the British Royal Mail) and the taxi-hailing company Hailo (which raised $100 million and in which Daimler took a 60% stake in 2016), returned to New York to start Thimble as his third venture. The company launched in 2016 under the name Verifly, initially insuring drone pilots.
Business model
Thimble acts as an insurance producer, distributing liability policies underwritten by a carrier partner (Markel as of 2019) directly to small businesses and independent workers through its own web and mobile channels. Its distinguishing commercial mechanic is time-scoped coverage sold in hourly, daily, weekly, monthly or annual increments.
Revenue derives from distributing liability insurance policies underwritten by a carrier partner, sold in flexible time increments to small-business and independent-worker customers.
Traction
The company reported it was on track to sell 100,000 policies by the end of 2019, with about 75% of customers uninsured prior to purchase and roughly 50% buying coverage for one day or less.
Latest developments
In October 2019 the company completed its rebrand from Verifly to Thimble and closed a $22 million Series A round led by IAC, lifting cumulative funding to $29 million.
▸Full profile — market position, technology, go-to-market, geography, history
Market position
Positioned as an insurtech start-up in the on-demand small-business liability segment, backed by IAC, Slow Ventures, AXA Venture Partners and Open Ocean.
Coverage can be bought in short, discrete increments — by the hour, day, week, month or year — through a self-service app or website, addressing buyers for whom an annual policy is not a fit; about half of customers purchased coverage for a single day or less.
Technology
A proprietary smartphone app and website through which customers quote and buy liability policies directly, without an agent intermediary.
Go-to-market
Direct-to-customer digital distribution via the company's website and mobile app, marketed by profession across more than 100 occupational categories.
Small businesses, independent workers and freelancers across more than 100 professions, including beauticians, DJs, dog walkers, handymen, landscapers and musicians. Management stated that only about 4% of customers identified as gig-economy workers and that roughly 75% had no insurance before buying from Thimble.
Geography
Operates in the United States; the company is headquartered in New York City.
History
Founded in 2016 as Verifly to insure drone pilots, the company expanded its product line to other categories of small business in response to customer demand for more insurance options. In October 2019 it rebranded as Thimble and simultaneously announced a $22 million Series A round, bringing total funding to $29 million.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Timeline · 3
launches, deals, and filingsThe insurtech announced a $22 million Series A round led by InterActiveCorp, with participation from existing investors Slow Ventures, AXA Venture Partners and Open Ocean, bringing total funding to $29 million.
$22M source ↗
The company, founded in 2016 as Verifly to insure drone pilots, rebranded to Thimble as part of its Series A financing to reflect an expanded product range serving many types of small business.
Coverage sold through Thimble's website and app was underwritten by Markel.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
▸Research sources · 8
primary sources listed
- Buy New Style Thimbles Online, Thimbles & Sewing Tools | Thimbles For You – ThimblesForYou.comthimblesforyou.com · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Thimble do?
- Thimble is a US insurtech selling on-demand liability insurance to small businesses and independent workers by the hour, day, week or month.
- Who are Thimble's investors?
- Thimble's investors include Frontline Ventures, MS&AD Ventures, OpenOcean, Valuestream Ventures, Atlantic Vantage Point.