Declaration of Independents: Patrick Dempsey

DOI_PatrickDempsey_ResizedPatrick Dempsey

Vice President
Dempsey Insurance
Norwood, Massachusetts

When Patrick Dempsey attended his first Big “I” Legislative Conference on a whim back in 2009, he “didn’t know anything” about the importance of the annual event. “But the Massachusetts agents who were there were all very experienced,” he says. “They knew the ropes, and they took me under their wing.”

A decade later, Dempsey has held several leadership roles at the state association level, helped revitalize the Massachusetts Young Agents Committee and was named InsurPac Young Agent of the Year for 2018.


Joe Leahy, our current chair, has said it best—one piece of bad legislation can do more damage than any of your competitors combined.


Not to underestimate the impact of an individual talking to their representative—their ears perk up when it’s their own constituent talking, because that’s who’s voting for them or who isn’t voting for them.

But what’s important to know about InsurPac is you don’t have to be the one hitting the pavement and going out and talking to politicians. by making a financial contribution, you can support people like the Big “I” government affairs team who are doing that 24/7, 365.


From an association and industry perspective, just get involved. My connection with the association started off by just taking a chance and showing up. If I hadn’t gone down to D.C., I wouldn’t have had half the opportunities to give back to the Young Agents and the state association that I have. That’s a big thing. It’s going to feel uncomfortable to go to a meeting for the first time or to participate in something you’ve never done before, but the more you show up, the more opportunities unfold. Things don’t just happen because you want them. Things happen because you do them.

From a work perspective, inside the office and selling, it’s a grind. The highs are high and the lows are low. But if you keep your head down and keep working, things build upon each other in this business. A book doesn’t happen overnight. The more you keep at it and the more you value your clients, treat them with respect and do what’s right for them, that will have a snowball effect for success.


It’s a family agency. My grandfather started it in 1947, and my father came on in the mid- to late ’70s and has run the agency since the early ’80s. I did not necessarily intend to go into insurance—I knew it was always something that was an option, and then when I got out of college with a degree in business, I decided to just see if I liked it. All of a sudden, one year became two, two years became three—I was surprised by how much I enjoyed the industry, and I was also surprised by how much I enjoyed working with my father. I’ve been in the insurance industry 11 years now.


The biggest thing is the relationship with the customers. You get to know people on a personal level. You really feel ultra-connected with the community where you live and work.


Forgetting to walk before I run. When I transitioned into commercial lines about five years ago, I didn’t know a lot about it, and I thought I could just hit a homerun right out of the gate. I thought, “Insurance is insurance”—that I could just flip a switch and suddenly I’d be doing commercial. What ended up happening was it took me twice as much work as if I had slowly built up knowledge and understanding and ability. It was a lot of long days and a lot of long nights of catching up on work I wasn’t able to do efficiently because I didn’t know it well enough.


The relationships that are established by agents with their customers and their communities. The ultra-large companies that want to sell direct won’t have an individual living in their town, contributing to a local charity or volunteering. You can’t duplicate or replace that with big business. You can only do that on a micro level.


At the same time, that comes as a weakness. You can’t always do the 24/7 thing, because it takes away from that relationship building. You don’t want to be like the big direct competitors, but at the same time, you do. It’s a give and take. You want to be able to offer the same services, but it will take away from that intimate customer connection if you completely replicate it.


If you don’t let the younger generation into the boardroom, in on the conversation, you’re going to miss out on their perspective, and it’s going to be to your disadvantage. But you can’t just put somebody at the top of the heap and expect them to do it. If they have a track record of doing good for the industry and the association, they’re more likely to be a good proponent for the industry. Massachusetts has done a good job of rewarding the responsibilities of those who have performed somewhat beyond the call of duty.

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