Thimble Names Terri Hitchcock Chief Insurance Officer

Hitchcock, a veteran of over 30 years in the P&C industry, joins Thimble from Perr&Knight where she was Director of the Product Design Practice.

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Thimble, a New York-based startup insurance distributor providing hourly policies for smaller SMBs and gig workers, has appointed Terri Hitchcock as Chief Insurance Officer.

Terri Hitchcock, Chief Insurance Officer, Thimble.

Hitchcock, a veteran of over 30 years in the property/casualty insurance industry, joins Thimble from Perr&Knight (Santa Monica, Calif.), where she was Director of the Product Design Practice. Hitchcock has also held executive positions at Affirmative Insurance (Addison, Texas), TIG Insurance Group (Spring, Texas), and the Zurich Insurance Group (Zurich). Her expertise spans standard property/casualty lines of business, professional liability insurance for all types of professionals and facilities, errors and omissions coverage and management liability coverages, according to a Thimble statement on Hitchcock’s appointment.

Hitchcock has consulted with Thimble since 2017, and was pivotal in bringing Thimble’s breakthrough on-demand and monthly general liability and professional liability insurance products, according to the company. In her new role as Chief Insurance Officer, she will oversee both existing and emerging products in Thimble’s offering.

Jay Bregman, Co-founder and CEO, Thimble.

“Terri is a big reason why we’ve built such a beloved brand among SMBs thus far,” comments Jay Bregman, CEO and Founder of Thimble. “Her leadership has been vital as we set out to change the landscape of insurance products and formats for modern business owners. Terri’s expertise is second to none, and as a full-time member of the team her leadership will provide incredible value as she accelerates the release of many new insurance products for small businesses.”

Big Believer in the Thimble Mission

“I’ve always been a big believer in the Thimble mission since the first time I met Jay,” Hitchcock comments. “Business insurance is in desperate need of evolution, and there’s a clear need for innovators like Thimble to act as a catalyst. We’re all committed to helping customers succeed on their own terms. I’m grateful to be joining the team in an official capacity and I’m excited to see where we take things next.”

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Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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