Dottie Chalmers Cutter is honored to be the HR leader of a long-standing family business, but it’s a role that comes with tremendous responsibility.
After all, what’s at stake goes beyond sales and
profitability to what will be the Chalmers’ legacy.
“I know I have big shoes to ;ll,” says Cutter, vice president of
operations at the Chalmers Insurance Group, based in Bridgton, Maine. She oversees 85 employees in the company’s commercial and personal lines and leads the area of agency assistance across its nine o;ces in Maine and New Hampshire. She
also supervises members of the middle-management team.
In January, Cutter and her cousin Jim bought the company
from her father and uncle, o;cially becoming the fourth generation to own and operate the business. The acquisition only
strengthened the cousins’ bond.
“We grew up on the same street in Bridgton, one mile apart.
We’re only one year apart in age—he’s older!—and we at-
tended Bowdoin College together. We have been working in
the family business together for 14 years, and we complement
Just like their predecessors did, she says.
“Jim is very much just like his dad, Bruce: the consummate
salesman. Jim thrives o; of the entire sales process—in par-
ticular, growing our niche specialty of insuring boys and girls
summer camps in New England. I, however, am more similar
to my dad, Bill, with an interest in and knack for insurance
operations and agency management. The business needs both
skill sets. It’s certainly an honor to walk in our fathers’ foot-
steps and carry on their great work and legacy.”
Cutter recently spoke to HR Magazine about her career
I’m the middle child, with one older brother, Nicholas, and
a younger sister, Marney. I grew up on the same street as my
grandparents and cousins. I loved sports and played tennis,
;eld hockey and basketball. Despite growing up on a golf
course, I didn’t pick up that game until I was in my 20s and
had started my insurance career. Had I known what a great
networking tool golf would be in the insurance industry, I
would’ve learned it a lot sooner!
PLANTING A SEED
When I was a child, my dad would always whisper “insur-
ance” in my ear. He thought that, out of his three children, I
would be the best ;t for the industry. At the time, I’d always
roll my eyes and say, “Oh, Dad,” but truth be told, insurance
was always in the back of my mind, so maybe the whispering
worked. All I know is that now I practice that same tech-
nique with my oldest daughter, So;a, who just turned 8. If
you ask her what she wants to be when she grows up, she’ll
reply “a Chalmers insurance agent, like my mom!”
Right out of college, I lived in Wellington, New Zealand, for
a year. That’s where I had spent a semester during my junior
year in college. I loved the abroad experience so much that
I learned about a program that granted work visas for several countries, including New Zealand. Since I had already
made friends there, I returned in 2004 and lived with my
Kiwi friends while working in sales at a sporting goods store.
CLIMBING THE CAREER LADDER
I started in personal lines sales selling home/auto/umbrella/
boat insurance. I serviced accounts and enjoyed the client
interaction. I felt it was important to understand the foundation of the business. After about ;ve years in sales, I moved
into management. My dad referred to my cousin Jim and
me as the “junior management” team. That name seemed to
stick even after Jim and I were handling all daily operations.
I ;nally told my dad, “I think you can drop the ‘junior’ now!”
When I ;rst moved into management, I worked closely under the mentorship of our then vice president of operations
and HR, Sherry DeBeradinis. She really took me under her
wing and introduced me to management, operations and
human resources. I was hungry for a more formal business
education, so I completed a two-year human resource management certi;cate program at the University of Southern
Maine. That gave me the foundation I was looking for to
better understand the HR function.
FINDING HER MOJO
What really jazzes me is building company culture and increasing motivation and engagement in the workplace. The
more engaged our employees are, the harder they’ll work,
which will positively impact our company. We think of it as
the 3 R’s: increase Referrals, build deeper Relationships and