# Jay Bregman

> Jay Bregman is a New York-based American entrepreneur who co-founded eCourier, Hailo and Thimble. His companies applied technology to courier dispatch, licensed-taxi booking and flexible small-business insurance. Arch acquired Thimble in 2023; he stepped down as its President in July 2025 and is now founder and CEO of Andel.

- **Role:** Founder & CEO at Andel
- **Organizations:** Andel, Thimble, Hailo, eCourier
- **From:** New York, United States
- **Nationality:** American
- **Education:** Undergraduate degree in Philosophy; magna cum laude; Phi Beta Kappa, Dartmouth College, MSc in Media & Communications Regulation and Policy, London School of Economics and Political Science
- **Known for:** Co-founded eCourier, which was later acquired by Royal Mail., Co-founded Hailo, which merged with Daimler-owned mytaxi in 2016., Co-founded Thimble and led it through its acquisition by Arch Insurance in 2023.

## Career timeline

- **2001** — Graduated from Dartmouth; later recalled an unsuccessful early venture, classof2001.com.
- **2003** — Co-founded eCourier in London with Tom Allason.
- **2008** — Navigated the financial crisis at eCourier; later described losses on individual deliveries and instability at its investment fund.
- **2011** — Hailo launched its London taxi-booking service with six co-founders, including three black-cab drivers.
- **2014** — Left Hailo and began developing Verifly.
- **2016** — Verifly launched on-demand drone insurance; Hailo agreed to merge with Daimler-owned mytaxi.
- **2019** — Verifly rebranded as Thimble and announced a $22 million Series A led by IAC.
- **2023** — Arch Insurance acquired Thimble; Bregman continued as President.
- **2025** — Stepped down as Thimble President in July; became founder and CEO of Andel.

## Achievements

- Co-founded eCourier, which was later acquired by Royal Mail.
- Co-founded Hailo, which merged with Daimler-owned mytaxi in 2016.
- Co-founded Thimble and led it through its acquisition by Arch Insurance in 2023.
- Thimble announced more than 170,000 small-business policies delivered since May 2018 at its April 2023 acquisition.
- Testified before the New York Senate Standing Committee on Internet and Technology on October 16, 2019.

## Latest updates

- **2026-07** — Contributed leadership advice to Adam Mendler’s article, warning that managers can become too far removed from day-to-day work.
- **2025-07** — Thimble announced that Ian Westerman succeeded Bregman as President, effective July 16, as Bregman pursued a new opportunity outside insurance.

## Links

- Website: https://about.me/jaybregman
- LinkedIn: https://www.linkedin.com/in/jaybregman/
- Twitter/X: https://twitter.com/jaybregman

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Profile page: https://yespress.io/jay-bregman
Published by YesPress — https://yespress.io
Last updated: 2026-10-25