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You are here: Home / unpublished / Plymouth Rock Unveils New Home Insurance Quoting Tool on ChatGPT

Plymouth Rock Unveils New Home Insurance Quoting Tool on ChatGPT

August 3, 2026 by AC Editor

Plymouth Rock home insurance quoting through ChatGPT
Plymouth Rock Home Assurance has launched real-time home insurance quoting through ChatGPT in six states.

Insurer says it is the first U.S. carrier to offer real-time homeowners insurance quotes directly within ChatGPT

Insurers are increasingly developing and deploying artificial intelligence tools across their operations as insurers become better versed in AI and what it can do for them. On the heels of Liberty Mutual, Simply Business, and EMPLOYERS, all of whom have launched a quoting tool on ChatGPT, another Boston-based insurer has now joined their ranks. Plymouth Rock announced that it has launched a new ChatGPT plugin that allows consumers to obtain real-time home insurance quotes directly through ChatGPT, an initiative the insurer says is the first of its kind among U.S. home insurance carriers.

“We’ve spent a decade offering the fastest, easiest way to buy home insurance,” said Bill Martin, President and CEO of Plymouth Rock Home Assurance. “Today, customers can get answers instantly through ChatGPT. We are the only home insurance carrier that can provide those answers. But speed alone isn’t enough. Customers want a carrier with the financial strength, claims-paying ability, and proven track record to stand behind those answers. Plymouth Rock delivers all the above.”

Not Just for Plymouth Rock Homeowners

One thing the company emphasized in a written communication to Agency Checklists is that this tool is for both agents and consumers.

“We believe that independent agents provide unique and personalized value to their clients, which is why we built our Home Policy Marketplace so agents can purchase direct-to-consumer policies, including those sold through ChatGPT. Policies can be added to their portfolios and serviced within their businesses.”

Homeowners Can Obtain Quotes Within ChatGPT

According to Plymouth Rock, the plugin allows an individual to obtain a personalized home insurance quote through a conversational interaction within ChatGPT rather than navigating multiple websites and forms.

Screenshot of a dashboard showing a home insurance quote: left vertical navigation with icons (New chat, Projects, Scheduled, Library, Plugins, Agents, Codex, GPTs) and a central panel titled 'Hi Bonnie, here’s your home quote' with Good Coverage ($139/mo), Better Coverage ($175/mo), Best Coverage ($218/mo) and a breakdown list of coverages on the right side.
A screenshot of Plymouth Rock’s new ChatGPT plugin

The company described the new capability as part of its broader digital strategy to simplify the insurance process from quote through claim. The launch is intended to combine its underwriting capabilities with emerging technology and provide consumers with another digital channel for obtaining home insurance quotes.

Available in Massachusetts and Five Other States

The new quoting capability is available in all six states where Plymouth Rock currently operates: Massachusetts, New Jersey, Pennsylvania, Connecticut, New York, and New Hampshire.

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