Thimble (insurance company)

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Founded2016; 8 years ago (2016)
  • Jay Bregman
  • Eugene Hertz
New York, NY
United States
  • General liability insurance
  • Professional liability insurance
  • Inland marine insurance

Thimble, is a United States-based business insurance company that was the first to offer small business owners a monthly and on-demand insurance policy.[1]

Thimble delivers insurance policies via its website as well as its iOS and Android applications. Thimble is the only company in the United States that allows a business owner to purchase liability insurance via a mobile application.

Thimble, originally founded as Verifly (Verifly Insurance Services, Inc. DBA Thimble), is founded by Jay Bregman and Eugene Hertz and backed by investors including IAC, Slow Ventures, and Open Ocean. The company raised $29 million as of October 2019.[2]



Thimble was founded in 2016 by Jay Bregman and Eugene Hertz. Bregman had founded two previous companies, eCourier which was sold to the Royal Mail, and Hailo, which was sold to Daimler Chrysler. Hertz was Chief Information Officer at Quidsi, an ecommerce company that was sold to Amazon for $545M.[3]

The company was originally founded as Verifly in 2016 and offered the first on-demand insurance for commercial drone pilots.[4]

In May of 2018, still as Verifly, the company expanded its offering to include more professions including handyman, contractors, landscapers, photographers, consultants, and more.[5]


In May of 2018, the company announced $7 million in funding with investors including Slow Ventures and Sam Shank, co-founder and CEO of HotelTonight.

In October of 2019, the company announced an additional $22 million in funding from IAC, Slow Venture, and Open Ocean Ventures.[6]

Name change

As the company expanded its business insurance offering beyond drone pilots and to cover contractors, handymen, photographers, DJs, and others, its original name, Verifly, was no longer relevant to its current and future customers. The company decided to rebrand to Thimble and relaunched a redesigned website and mobile application in October of 2019.[7][8]


Thimble was the first company to offer on-demand General Liability Insurance for as little as one hour. The policies are underwritten and reinsured by Markel Corporation.

In February of 2020, the company launched the first-ever on-demand professional liability insurance.

In March of 2020, the company launched a monthly subscription product. Unlike an annual insurance policy with monthly payments, Thimble’s monthly product requires no upfront deposits and allows a policyholder to cancel at any time without incurring fees or penalties. To adapt to the uncertainty of COVID-19, Thimble introduced a feature for its monthly customers to pause[9] their coverage for up to 30 days.

Thimble allows users to purchase insurance digitally without needing to talk to an insurance broker. Customers can use their website as well as their mobile applications to both purchase and modify their policy. All policy documents including a Certificate of Insurance are delivered instantly via email. Thimble is the only company to offer business insurance via a mobile application in the United States.


Thimble partners with a number of companies to offer insurance via its API, including Angie’s List.[10]

Thimble has also partnered with Hiscox, another Small Business Insurance company, to offer Hiscox’s customers short-term liability insurance.[11]

In August 2020, Thimble was selected by Lloyd’s to join its innovation accelerator program where the two companies will work on a Pandemic Business Interruption Insurance offering.[12]


In 2020, Thimble was recognized as the Best for the Smallest Businesses on’s “The Best Business Insurance of 2020” list.[13]


  1. "Thimble Insurance Review". The balance small business. The balance small business. Retrieved 1 September 2020.
  2. "Verifly rebrands into Thimble, raises millions in Series A funding". Insurance Business America. Insurance Business America. Retrieved 2 September 2020.
  3. "Quidsi". crunchbase. Retrieved 2020-10-01.
  4. "Verifly launches drone insurance by the flight, and on-demand in the US". TechCrunch. Retrieved 2020-08-23.
  5. "Verifly launches a business insurance product for gig economy workers". TechCrunch. Retrieved 2020-08-21.
  6. "Newly rebranded Thimble raises $22M to bring flexible insurance to the gig economy". TechCrunch. Retrieved 2020-08-21.
  7. "Verifly rebrands into Thimble, raises millions in Series A funding". Insurance Business Mag. Insurance Business Mag. Retrieved 2 September 2020.
  8. "Meet the insurtech: Thimble". Digital Insurance. Digital Insurance. Retrieved 27 September 2020.
  9. "Thimble Now Allows Small Businesses to Pause Their Business Insurance". Coverager. Coverager. Retrieved 23 August 2020.
  10. "Angie's List Partners with Thimble to offer Flexible Insurance Options for Small Businesses". Coverager. Coverager. Retrieved 23 August 2020.
  11. "Hiscox, Thimble to Offer Short-Term Business Insurance Plans". Insurance Journal. Insurance Journal. Retrieved 22 August 2020.
  12. "Has Lloyd's just found the answer for pandemic insurance cover?". Insurance Business America. Insurance Business America. Retrieved 23 August 2020.
  13. "The Best Business Insurance 2020". Retrieved 1 September 2020.

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