Career Lessons from Dottie Chalmers Cutter: Homegrown Leader

November 30, 2018

Originally published in HR Magazine

For the co-owner of a fourth-generation business, a strong work ethic is all in the family.

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 fill,” 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 offices 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, officially 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 attended Bowdoin College together. We have been working in the family business together for 14 years, and we complement each other.”

Just like their predecessors did, she says.

“Jim is very much just like his dad, Bruce: the consummate salesman. Jim thrives off of the entire sales process—in particular, 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’ footsteps and carry on their great work and legacy.”

Cutter recently spoke to HR Magazine about her career journey.

Family Ties   

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, field 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 “insurance” in my ear. He thought that, out of his three children, I would be the best fit 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 technique with my oldest daughter, Sofia, 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!” 

Study Abroad  

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 five 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 finally told my dad, “I think you can drop the ‘junior’ now!” 

Building Capacity  

When I first 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 certificate 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 increase Retention, which will ultimately grow the bottom line. 

In a leadership role, it is so important to continuously coach, reward and be clear with employees about the big picture. If I do those things well, motivation will remain high, and that’s exciting to me as a business leader.

Learning and Growing  

For the past three years, I’ve worked with an executive coach who has helped me become a better leader. I’ve learned about the importance of positive reinforcement [and] how to build commitment, set clear expectations, capitalize on coaching moments and practice “humble inquiry.” I’ve also stayed on top of trends in HR. For example, gone are the days of the annual performance review. Today, it’s all about having individualized development plans and providing continuous coaching. 


Extended Family   

I am an active member of the Greater Portland Institute for Family-Owned Business (IFOB)—a wonderful nonprofit created for the benefit of Maine family-owned businesses. Through that association, I’m also active in its affiliate chapters, NextGen and Women in Family Owned Business, and I serve on the program committee and help the IFOB select more than 40 educational classes to offer to its members. I love to share knowledge and help inspire people from other family-owned businesses.

Dottie Chalmers Cutter and her cousin Jim are the fourth generation to run their family’s insurance business.

Leadership Lessons  

Hire for attitude, train on aptitude. Aptitude can be taught, but you can’t change a person’s attitude. 

Be transparent. Employees want to hear from the leadership team as often as possible, so find ways to engage and communicate with others often.

Do more listening and less talking. The art of the humble inquiry is a skill. Ask questions of genuine interest to get a better understanding of your co-workers as people. Be empathetic and have a good listening ear. You don’t need to solve every problem, but try to understand others’ feelings and perspectives. Let them know that you know where they’re coming from.

Never doubt the power of the handwritten 'thank you' note. Recently, I’ve made it a personal goal to do more to recognize my co-workers, clients and carrier partners for their efforts. 

Community Roots  

One of our core values is giving back to our community. It is something I was taught to do by my father and grandfather. They were such wonderful role models and stewards in their community, involved in countless boards and nonprofits, and they are generous in their charitable contributions and participation in several larger capital campaigns. We want our local communities to thrive. In fact, if employees volunteer during business hours, we comp them for their time. We believe it’s that important! 

Focus on the Future  

I see staffing and talent development as an ongoing challenge for us in the next five to 10 years. The average age of the workforce in our industry is 55, so our strategy will be to make staffing a year-round process instead of only tackling it on an as-needed basis. We need to be proactive about getting more young professionals into insurance. It’s a great career, and there are so many job opportunities within the industry.

Her Favorite Business Book  

Find Your Why (Portfolio, 2017) by Simon Sinek. It’s a quick read that talks about how we are all entitled to wake up in the morning inspired to go to work, feel safe when we’re there and return home fulfilled at the end of the day. Find Your Why is a step-by-step guide to help you identify your purpose and put you on a path to long-term success and fulfillment.  

Desda Moss is managing editor of HR Magazine.  Photographs by Nina Cutter

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