Dottie Chalmers Cutter
Chief Operating Officer, Chalmers Insurance Group
Q
You’re a fourth-generation owner of your family’s business. Do you feel any added pressure to keep this successful business successful?
A
Absolutely. My dad and my uncle, who are the third generation, were absolutely revered, not just in the insurance industry but in our local community. My dad was always my biggest mentor. He told me, “Put your own stamp on this and make it your own.” So I did exactly that. And I think I finally hit my groove, and I’ve earned the respect of our workforce from rolling up my sleeves and starting from the bottom.
Favorite Vacation Spot: “I just took my family to Banff, Canada, in June, and it was the first international trip we took as a family and hopefully the first of many, because I have promised them New Zealand.”
Favorite Ski Slope In Maine: Pleasant Mountain (“Because I grew up in Bridgton, and that was the hill right in Bridgton. I also love Sugarloaf Mountain, which is in the Carrabassett Valley.”)
Favorite Movie: The Devil Wears Prada
Favorite Musician: Pink
Favorite Book: “I did recently get really into Colleen Hoover. I like her writing style. If it was a business leadership book, it would be Simon Sinek. Find Your Why was one of the books that I really took a hold to.”
Favorite Restaurant in the Bridgton Area: “I’m going to go more Portland. It’s a foodie town, so I would say Scales is definitely one of the best.”
Favorite Dish at Scales: Roasted halibut with brown butter (“I love the mussels there as well. Or the lobster roll, because, you know, I’m a Maine girl, so I can’t not like a good lobster roll.”)
Q
What were the most significant changes you brought to the leadership of the company?
A
Five or six years ago, I took a 360 assessment with a leadership coach. It was very humbling for me, because I realized I had some things I needed to change in my leadership style. My co-workers didn’t feel like they were being recognized enough. Although I’m a very empathetic person, it wasn’t coming across in my daily interactions. So I started recognizing people all the time. I started small, with birthday cards and work anniversary cards, which I still do to this day, mailed to their home address. They so appreciate the gesture because not only do I wish them a happy birthday or thank them for their years of service, but I specifically describe the ways in which they’ve impacted the business. I started to create this culture of recognition. I’m actually a trained leadership coach and I facilitate a sixmonth leadership program for emerging leaders within the company.
Q
Tell me about Bridgton, Maine.
A
Bridgton is a special place in western Maine. It’s surrounded by mountains and lakes, and, honestly, it’s a little slice of heaven. It’s 30 minutes to North Conway, New Hampshire, so you have the draw of the Mount Washington Valley, and [we’re] about an hour west of Portland, Maine. We’re lucky to actually have a small ski area in Bridgton called Pleasant Mountain. I grew up skiing that mountain starting at age 3. My kids now ski that mountain with us today.
Q
What does a perfect weekend look like for you?
A
A perfect weekend would be one like the one I just had. I got to watch my son play soccer on the travel soccer team, and then I got to see my daughter play field hockey. I’m dropping off my oldest to gymnastics, because she’s a competitive gymnast. I’m always doing a workout, usually first thing in the morning, so I’m either riding my Peloton bike or I’m weightlifting in my basement. And then we’re coming home and we’re taking a breath, and we might be walking the dog in our neighborhood, and we’re having a family dinner, where we all go around the table and talk about what was the “rose and thorn” of our day.
Q
What would your co-workers be surprised to learn about you?
A
My co-workers always were surprised to know that I was so shy as a child. Knowing who I am today, they would say, “No way was Dottie a wallflower.”
Q
How would your co-workers describe your management style?
A
Coaching leader, empathetic, and thoughtful.
Q
If you could change one thing about the insurance industry, what would it be?
A
I’d love to see more women in leadership positions, both on the carrier and agency side. A big piece of this is being vulnerable, admitting when failures arise, and showing our imperfections. I believe that women do this more instinctively than men, and this is an advantage.
Q
What gives you your leader’s edge?
A
I think it’s the ability to be vulnerable and lead with empathy, curiosity, and compassion. Being able to teach leadership practices in the workplace through our Emerging Leaders Program allows me to inspire the future leaders at Chalmers, and that’s pretty cool.
