Arch Insurance acquires Thimble

Arch Insurance, part of Arch Capital Group, has acquired small business insurance startup Thimble.

The story of Thimble begins in 2015, when Jay Bregman launched Verifly, a startup offering on-demand insurance for drones. Verifly eventually added on-demand liability insurance and in 2019, it announced a new brand – Thimble – along with a $22 million Series A round. During that time, Thimble shared that it sold over 100k policies, with 50% of these policies covering a single day or less. Today, Thimble says it sold over 170k policies.

Thimble works with a variety of carriers including Markel and Employers. The Thimble team will continue growing the business with its existing carrier partners and offer new solutions through Arch.

Last year, Thimble laid off 33% of its workforce.

“At Arch, we’re always looking to expand our digital solutions and create new, easy ways to do business with us. Thimble makes insurance easy. The Thimble team has created a best-in-class digital experience for small business customers and agents to acquire and manage insurance. We’re excited about growing the Thimble platform and applying many of its digital practices across Arch to better serve our partners.” – Jay Rajendra, Arch’s chief strategy and innovation officer.

“We are delighted to join the Arch family. The entire Thimble team is looking forward to working with Arch and our existing carrier partners to grow the platform. I’m equally excited to see how our team’s digital experience can benefit Arch and its distribution partners.” – Jay Bregman, co-founder of Thimble.

Bottom Line: Making insurance easy to buy, doesn’t make insurance easy to sell.