Thimble Names Richard Stamets SVP of Business Development 

Stamets is tasked with scaling Thimble’s technology-driven flexible insurance proposition, working with insurance brokers, agents and wholesalers to better serve their small business customers.

(Image credit: Dmitriy ds_30.)

Thimble, a startup insurance distributor providing hourly policies for smaller SMBs and gig workers, has announced the hiring of Richard Stamets as Senior Vice President of Business Development. A Thimble statement says Stamets will lead the company’s’s efforts to engage with insurance agents, brokers and wholesalers toward its goal of providing flexible business insurance options to small businesses at scale.

Richard Stamets, SVP Business Development, Thimble.

Stamets’ hiring comes in the wake of 2020 market innovations such as the company’s debuting its Thimble Monthly policy and the Thimble Pause to allow small businesses more flexible coverage, managed through Thimble app. The company also announced partnerships with Hiscox and Angie’s List to offer Thimble’s flexible policies at scale.

“We want the broker community to know that Thimble is on their side,” said Stamets. “Brokers play a critical role in the insurance ecosystem, as trusted advisors and guides to their clients. Thimble empowers them with new product options that match the needs of current business owners, better customer management tools, and outstanding commissions. All of this is designed to help insurance pros who’ve dedicated their careers to helping their customers succeed, and are looking for every advantage as they chart a course forward.”

Prior to joining Thimble, Stamets was the Head of Underwriting at Attune Insurance. Before Attune, he was VP of Small Business at Starr Companies, Vice President of Programs at Hamilton Insurance Group, and spent eight years with AIG in multiple positions. Stamets’ expertise in the industry is vast, leveraging technology in underwriting, sales and distribution management, and executive leadership.

Jay Bregman, Co-founder and CEO, Thimble.

Invaluable Guidance

“Rich’s experience in InsurTech and knowledge of the industry will be a huge asset to our team,” said Jay Bregman, CEO and founder, Thimble. “His guidance will be invaluable as we grow our offerings for both small businesses and our industry and wholesale partners. Our team could not be more excited to have him on board.”

Interested brokers can set up a Thimble account in as little as 30 seconds at, a company statement says. Once registered, brokers can earn commissions via Thimble’s simple referral processes: sending their unique link, building a quote, or purchasing a policy on behalf of a customer. Customer quotes require just two pieces of information– job type and location– and coverage can be binded in as little as 60 seconds. Brokers maintain full ownership of the customer relationship.

Thimble reports that, to date, more than 6,000 brokers are taking advantage of the Thimble Broker Program, helping their customers access coverage quickly and efficiently.

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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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