Jay Bregman, co-founder and CEO of Thimble, has reinvented insurance for small businesses through an innovative and on-demand approach. A graduate of Dartmouth College and residing in New York, he has captured the needs of freelancers by creating a platform that offers insurance solutions tailored to the realities of today’s market. With over 500 connections on LinkedIn, Bregman is an influential figure in the insurance and Fintech sectors, and his influence continues to grow due to his bold vision.
Jay Bregman, a name that resonates in the world of modern insurance, is the visionary behind Thimble. This entrepreneurial pioneer has distinguished himself by redefining insurance for small businesses. Before founding Thimble, Jay made a name for himself as a serial entrepreneur, drawing inspiration from shifts in the gig economy and freelancers.
With a solid background from Dartmouth College and significant experience under his belt, Jay has seen beyond traditional practices. In 2016, with Eugene Hertz, he launched Verifly, a bold first initiative offering “day-of” insurance for drone operators. Following its resounding success, the idea was expanded to different sectors under the name Thimble, thus meeting the needs of an ever-evolving economy.
Based in New York but with influence that extends far beyond, Jay has made Thimble a key player in the insurance sector, helping small businesses thrive on their own terms. With his expertise and modern vision, Jay Bregman continues to transform this landscape with innovative solutions tailored to today’s challenges. A leader who inspires through his ability to anticipate and respond to the changing needs of the market.
The Beginnings of Jay Bregman
Jay Bregman has always been passionate about innovation and business. He attended Dartmouth College where he sharpened his entrepreneurial spirit and received an education that would allow him to turn innovative ideas into successful companies. Although Jay is now based in New York, he has managed to weave an impressive global network with over 500 connections on LinkedIn. This network has helped propel his career and create a lasting impact in the business world.
The Rise of Thimble
In 2016, Jay Bregman co-founded Thimble, a company that is revolutionizing insurance by offering on-demand solutions for small businesses and freelancers. This idea was born from his previous experience with Verifly, where he introduced the concept of “day-of” insurance for drone operators. Thimble quickly established itself as a go-to choice for professionals seeking simplified and personalized coverage, specially designed for the challenges of the freelancer economy. To listen to an in-depth conversation with Jay Bregman, check out this podcast.
Jay Bregman and the Future of Insurance
Through his entrepreneurial spirit and determination, Jay Bregman has enabled Thimble to join the Arch Insurance family, an evolution that has opened new opportunities for the company. According to Jay, this integration will allow Thimble to continue to grow while benefiting from Arch’s expertise and network. Not only does Thimble offer insurance solutions for various professionals such as artisans, DJs, and estheticians, but it also remains at the forefront of innovations in the sector. To discover more about Thimble’s evolution and the lessons Jay has learned over the years, feel free to read the full interview available on Global Fintech Series.
