About Us

We are a family run insurance agency that has been operating for 70 years and three generations. Our goal has always been to provide a quality insurance product coupled with a personal touch that customers will value. 
We represent a number of carriers in order to provide multiple options for personal and commercial insurance. All of our companies are listed on our Pay-a-Bill page & Submit a Claim page. We are confident that if you have a need for a policy or questions on insurance that we can find the company or answer for you.
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Roger Dempsey

Robert Dempsey

President / CEO

I am a 43 year veteran of the Insurance Business, having started with my Dad in 1975 after graduating from Babson College with an MBA degree. Our business is focused on the customer, who always comes first. We are family owned so when you call Dempsey Insurance, you will always find a Dempsey at the office.

Patrick Dempsey

Patrick Dempsey

Vice President

I have been in the industry 10 years and started in the family business upon graduating from Gettysburg College. Over the years I have worked in every segment of the business from reception to claims to personal lines to commercial lines. I live in Norwood with my wife and two children. I currently serve on the Massachusetts Association of Insurance Agents board of directors and also on the board for In-Control Family Foundation.

Kate Dempsey

Kate Dempsey

Claims

I am the Claims Manager in the office. I am a licensed agent and have been in the insurance industry for four years. Prior to joining the office I spent ten years in marketing and public relations with a focus in non-profit. I live in Norwood with my husband and two children.