Thimble announces leadership transition: Ian Westerman appointed president

Liability and small business insurance provider Thimble has announced a transition in its executive leadership: Ian Westerman, previously Thimble’s SVP of Finance, has been appointed President, effective immediately.

Westerman joined Thimble two years ago from Pie Insurance, bringing with him deep expertise in insurance strategy and operations. Since then, Westerman has played a key role in streamlining processes and supporting Thimble’s rapid growth and profitability.

Jay Bregman, one of Thimble’s original founders who led the company since 2014, has decided to step down from his role as President to pursue a new opportunity outside insurance. This news comes as Thimble hits its ninth-consecutive quarter of growth under parent company, Arch Insurance North America (Arch Insurance).

“I’m honored to step into the role of President at such an exciting time for Thimble. Jay has established outstanding values, among them a culture of innovation, customer focus and agility. I look forward to building on that foundation; helping Thimble grow, scale and deliver even more value to our customers and partners. With Arch’s support, Thimble is on track to become one of the biggest players in America.” – Ian Westerman, President, Thimble.

“We thank Jay Bregman for all of his contributions and wish him well in his future endeavors outside insurance. Ian is a seasoned leader who has played a huge part in Thimble’s recent success and growth. I am excited to see what he can do as President in this planned succession.” – Jay Rajendra, Chief Strategy and Innovation Officer for Arch Insurance’s parent, Arch Capital Group Ltd.