Agent Spotlight: Ryan O’Connor, O’Connor & Co. Insurance Agency, Inc.

Ryan O’Connor

Chief Operating Officer

O’Connor & Co. Insurance Agency Inc., Webster, MA

Ryan O’Connor grew up around the insurance industry – he is the second generation of O’Connors at the agency his parents, Daniel and Karen, founded. He joined the family business four years ago as his parents began to prepare for the future of the agency. It was a perfect fit for Ryan O’Connor, who enjoys the sales process and embraces the challenges each day brings. “I took the jump, and I couldn’t be happier I did,” he said. “The industry is constantly changing and evolving, which matches my personality as I am always looking for a challenge.”


What would you do for a career if you weren’t in insurance? Any kind of sales. I am not a hard-sale kind of person. I have never used a pressure method. However, my strong suit has always been the ability to talk to people from all walks of life. I can jump from a conversation with a contractor to a conversation with someone who runs a healthcare company in the course of five minutes. I enjoy getting to know people and I enjoy getting to know their businesses.

Why should people consider a career in insurance? Stability. Although the market is tumultuous right now, the insurance industry is not going anywhere. There will be winners and losers for sure, but that is what is exciting. It also provides an environment where you can always learn something new.

What excites you about the industry? Right now the market is very difficult. I have always looked forward to the tough times as I believe we will come out of that much better.

What are common misconceptions about the industry/as a career that you don’t agree with? I think a lot of people in my generation view the industry as boring or an industry of the past. I think the opposite. Insurance provides a vast opportunity for growth.

Where do you see the industry in 10-20 years? I am excited about the future. Again, I think there will be winners and losers on the agency and company side, but I think there are great opportunities for the ones who can stand through the storm and not run for the hills. Rates have long been too low in many areas and I do think rates will continue to climb, but in the near future, they will reach levels of where they need to be to drive profitability. The need for insurance will not go anywhere – the names of the businesses selling it will.

What are your goals for the agency? We are on a growth path. We have almost doubled in premium size over the past five years through organic growth and acquisition, and we plan to keep this going.

What was your first job? McDonalds at 15 or 16.

What is the most used tool/resource that has made you the most successful? I find just being a good listener can get you a long way. You can learn a lot about what a customer’s issues are that they need fixing by just listening. If you’re then able to fix those issues easily, you can gain a lifelong customer.

What do you like to do outside of the office? I am a Boston Celtics fan through and through. I love a game at the Garden. Most of all, I love the time I get to enjoy spending with my wife and kids.



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