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Thimble Announces Leadership Transition: Ian Westerman Appointed President
New York, NY (July 16, 2025) – Thimble, the leader in fast, easy and flexible small business insurance, 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,” said Westerman. “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.”
“We thank Jay Bregman for all of his contributions and wish him well in his future endeavors outside insurance,” said Jay Rajendra, Chief Strategy and Innovation Officer for Arch Insurance’s parent, Arch Capital Group Ltd. “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.”
About Arch Insurance North America
Arch Insurance North America, part of Arch Capital Group Ltd., includes Arch’s insurance operations in the United States and Canada. Business in the U.S. is written by Arch Insurance Company, Arch Specialty Insurance Company, Arch Property & Casualty Insurance Company, Arch Wilsure Insurance Company and Arch Indemnity Insurance Company. Business in Canada is written by Arch Insurance Canada Ltd.
About Arch Capital Group Ltd.
Arch Capital Group Ltd. (Nasdaq: ACGL) is a publicly listed Bermuda exempted company with approximately $24.3 billion in capital at March 31, 2025. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.
About Thimble
Thimble is dedicated to delivering quick, flexible, and hassle-free insurance solutions for small businesses and independent professionals. Since its founding, Thimble has helped simplify insurance, making it affordable, accessible, and tailored to modern business needs.
Thimble helps small businesses acquire general and professional liability, business equipment, commercial property, events and other types of insurance coverage via a proprietary digital platform. Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents.
Media Contact
Han Dang
Thimble Chief of Staff
press@thimble.com