Meet WebFirst Insurance President Kathleen O’Sullivan

Updated August 3, 2023  |   Published July 28, 2022

In early 2022, Kathleen O’Sullivan was promoted to President of WebFirst Insurance, LLC. We took some time to sit down with Kathleen to highlight her career, learn more about her journey through the insurance world, and why she loves to work in insurance.


Q: How did your career start?

A: My life before insurance was a stay at home mom to my three children. I was blessed to have that time and opportunity to do so. My career in insurance did not begin until 1998. Back in those days you looked for jobs in the Worcester Telegram and Gazette, and I saw an ad posted for a customer service rep at Mancuso-Nowak Insurance agency. I had no experience but they took a chance on me. They sent me to some classes for me to be educated on coverages and insurance language. I worked there as a customer service representative for many years. Working at Mancuso-Nowak was a good starting point for me, and a good agency to work with. I enjoyed my years with them.


Q: What did your early career at WebFirst Insurance look like?

A: I was hired as a customer service representative at WebFirst Insurance in 2008. That position was short lived. I became an office manager in 2009, which was a lot different than what I previously had experience with. It was a challenge going from working with my colleagues to managing their everyday tasks, but it was a welcome challenge.

I worked as an office manager until 2021, so the majority of my career here at WebFirst Insurance has been under that role. During that time, I experienced a significant amount of growth in my knowledge and experience with insurance. Our former President, Marty Barrett, encouraged me to obtain insurance licenses, to become a fully licensed insurance agent. The first one that I obtained was the personal lines license, which I passed in 2012. The second was the property and casual license, which I obtained in 2015 and the last was the Life Accident and Health license, which I obtained in 2018. Obtaining these licenses gave me a greater understanding of various insurance products to better serve our clients.


Q: How have your responsibilities changed over the past couple of years?

A: In 2021, I was promoted from office manager to Vice President. I began to work with the former president closely, assisting him on daily responsibilities, growth, budgets, and strategic planning for WebFirst Insurance. I also worked on insurance products for our parent company, Webster First Federal Credit Union. I took on responsibilities related to insurance for financial institution bond, professional liability, director’s and officer’s liability, and all employee benefits. Now, working as the President, my responsibilities have once again changed. I now oversee everything related to WebFirst Insurance; I manage both of our offices, prepare budget expectations, negotiate contracts, and meet with representatives from our providers on a regular basis.


Q: What makes you love working in insurance so much?

A: The relationships that I have made along the way is what is most important to me. It is so nice over the years to feel that you have developed a common bond with your clients. It is now that some of our long-term clients are bringing their children in for insurance for their first car, renters insurance or first home. It is a such a good feeling. This to me conveys the trust they put in me personally and as their insurance advisor. Everyone needs insurance from putting a car on the road, obtaining a mortgage or starting a business. All these things have financial impacts on our lives. Just knowing that I can assist my clients with proper coverage to protect their assets is what it is all about.


Q: What has been your favorite memories working at WebFirst Insurance?

A: One of my favorite memories occurred right after I had obtained my Property & Casualty Insurance license. We had a client with a homeowners policy who stated he was moving out of state and needed to change the insurance policy as the property would be rented. There were multiple dwellings on the property to be rented with an in ground pool in the middle. I am looking at liability issues but decided to dive right in.

As our conversations grew both in person and digitally, the liability issues kept growing. There’s a very large barn with woodworking going on to sell cabinets but no foot traffic to home, then later the son will now have an archery range on premise to sell bows and arrows with foot traffic. More liability! My first attempt at commercial insurance and I am having the feeling of how do I get him the proper coverage? I was feeling very overwhelmed as the coverage needed was continuously changing. Long and short of this story I hit many stone walls but I was able to get this accomplished with appropriate coverage. It was a period of learning and of satisfaction that I could provide him with what he needed.