Agent Spotlight: Michael Cheeseman, Cheeseman Insurance Group

Michael Cheeseman, Commercial Lines Account Executive

Cheeseman Insurance Group: Burlington, Milton & Vergennes, Vermont

Michael Cheeseman joined the insurance industry in 2010, focusing on Commercial Lines insurance. As his agency is the family business, his father introduced him to the industry and mentored him. “I had to convince him to let me come work for Cheeseman Insurance out of college, as he wanted me to try something else first to make sure I really wanted to have a career in insurance,” he said. “Luckily, he let me in!” Mike believes insurance is a rewarding career choice with much opportunity for growth, and he is excited about how the industry continues to evolve. He is currently working toward his CIC designation.

Why have you stayed in the industry? I really enjoy how each day in insurance provides a new challenge and/or opportunity. You find yourself doing something different every day which makes this industry interesting. One of my favorite parts of the business is getting to build relationships with my insureds and the company personnel.

What would you do for a career if you weren’t in insurance? This is a hard one for me as insurance checks all the boxes. I can’t think of another career that would do the same. I think I would try to find any job at Augusta National and hope for a golf membership if I did not work in insurance.

What is a misconception about insurance you want to clear up? I think the most underrated career is insurance. When I was in college, professors would mention working in investments, marketing, banking, and law. I find that the majority of people end up stumbling into insurance, and once they are in it, they stay in it. I wish a career in insurance would get more recognition from the start. Trust is the biggest obstacle I see clients have with insurance carriers. I think this stems from having unrealistic expectations of what is covered under insurance. If insureds were able to see the other side of the insurance process, they would see our companies are here to provide the best coverage for them.

What do you see in the industry in 10-20 years? I think technology will continue to play a huge role in the future of insurance. I hope we maintain the appropriate balance of these technological advances and the personal relationships we establish with insureds.

What do you think of when you think about Union Mutual? I think of an Insurance Company that values the Agency-Company Relationship. You will not find a more personal relationship anywhere in the insurance industry. Our agency would not be where we are today without our partnership with Union Mutual.

What are some of the ways you see people from our industry making a difference in the world? Our industry gives back to the community whether it is volunteering or charitable giving. Union Mutual is a pioneer for this with their Charitable Giving Fund and through our agency has helped donate funds to local youth organizations.

What is the most important leadership lesson you have learned, and how is it valuable to you today? That you learn more from losing than you do from winning, and knowing how to lose is important. In Major League Baseball, a career batting average of .300 gets you into the Hall of Fame. With this average, you lose 7 out of 10 times, which would break most people. I take this approach in sales because whenever I lose, it fuels me to do better.

What do you like to do outside of the office, and how do you create a work-life balance? This is a hard one especially being in a family business working with my father. I was able to learn this balance playing college baseball. My coaches would tell us that everything stays on the field, and nothing transfers off the diamond. I am grateful for this experience as baseball taught me work life separation even before starting a career in insurance. Outside of business hours I am a husband, father & a son. I really enjoy traveling with my wife and two daughters, fishing and playing golf. My most favorite travel destination is the Greek isles.  I really enjoy books about sports, The ticket out: Darryl Strawberry and the boys of Crenshaw, and Eight Men Out are two of my favorite books.


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