Megan Carroll

President

Stein Insurance

Lindstrom, Minnesota

“I worked as a property & casualty reinsurance broker at Willis Re," explains Megan Carroll. “That was my first 'big kid' job." However, the absence of a succession plan at her family's fourth-generation independent insurance agency and a desire to keep it family-owned drew Carroll into the family business in 2017.

“I took a substantial pay cut and started from the ground up at Stein Insurance," she says. “It felt like a huge risk at the time but, looking back now, it was definitely the right move."

Since then, Carroll has become a part owner and president of the business, a process in which she has stepped up professionally and grown into a leadership position while learning the ropes of agency management and p&c insurance.

What is your philosophy to leadership?

It is rooted in the belief that I can make a meaningful impact on my employees' lives. Work takes up so much of our time, and if I can create an environment that improves their day-to-day experience, then I feel like I'm making a difference.

Challenges to becoming the agency president?

I'm related to the two previous owners, so I've had to prove myself to show I'm worthy of this role. I also work with people who've been in this industry far longer than I have. Many have been at this firm for years and that dynamic adds complexity.

Taking the Kolbe assessment?

It affirmed that I'm in the right role as a business owner. It also helped me recognize that some things I've seen as weaknesses are actually strengths. I used to think procrastination meant I was disorganized, but the test reframed it as an ability to thrive under pressure. The test has also helped identify where
I need support. 

Taking a forward view?

One of the biggest challenges in this transition into becoming the agency president has been that I'm early in my career and not afraid to take risks, spend money, and try new things to see what works—I have the time to let those investments pay off. In contrast, my uncle, who was preparing for retirement, prioritized the agency's value. This difference in priorities often created roadblocks.

Involvement with Big I Minnesota Emerging Leaders?

Getting involved with the Big I Minnesota Emerging Leaders, the state young agents committee (YAC), was transformative. I was encouraged to join by colleagues who were deeply involved with Big I Minnesota. I started attending events and became president of Big I Minnesota Emerging Leaders.

The networking has been invaluable. Early in my career, I leaned heavily on experienced peers to solve problems and learn. Now, as an owner, those connections help ensure our firm doesn't become isolated. The Big “I" has provided a chance to give back to an industry that's treated me very well. I plan to stay involved and, eventually, hope to mentor others in the same way I've been mentored.

How has becoming a parent changed the way you work?

Becoming a parent has definitely changed the way I work. For years, I didn't fully grasp how much parents working full time were juggling—leaving work at 5 p.m. sharp, managing family priorities, and all that. I think our generation is in a particularly tough spot. We're still stuck in the traditional 40-hour workweek, but unlike previous eras, we don't have a partner at home handling everything. Both parents are working, and that requires managing family responsibilities on top of everything else.

These days, I can't work 60-hour weeks anymore. I'm setting stricter boundaries, cutting out at 5 p.m., sometimes earlier if my child is sick or something urgent comes up. It's a balancing act that requires major reprioritization. Honestly, it feels like I'm working two jobs, and I'm trying to take both seriously.

How has parenthood altered your approach to management?

I'm committed to fostering a more family-friendly environment at work. I'm firmly against the rigid 40-hour workweek—it feels outdated, especially given that it was designed during Henry Ford's time when households often had one income and a completely different structure. We're not working assembly lines anymore and hours logged aren't always the best measure of productivity.

To reflect that, we've dropped our agency's workweek to 35 hours. The office is only open to the public 30 hours a week, which gives employees some quiet time to focus without interruptions. The idea is to give people time to recharge, come back refreshed and perform better without burning out.

Burnout is real, and when kids are involved, it's even tougher. My philosophy is that life doesn't have to be about squeezing every last ounce of productivity from people. If my employees need to work 60 hours a week, that means I need to hire more people. It's not healthy and it won't create happy, productive team members. I also believe this flexibility makes us more competitive as an employer. If employees are engaged and feel connected to their work, the customers can feel the enthusiasm. The customer experience is improved. 

What should young professionals remember about leadership and career development?

First, remember it's a marathon, not a sprint. Whether you're aiming to be an agent or moving into leadership, it's all about building relationships and accounts brick by brick. Retention and reputation are critical in this industry, so patience and consistency are key.

And seek out mentorship. Before you accept a job offer, ensure the company has a solid mentorship program and that the mentor is genuinely invested in you. Without that guidance, the path can be unnecessarily long and filled with avoidable mistakes.

Also, don't be afraid to put yourself out there. Set your ego aside, take risks and don't worry about looking silly. People don't remember your “failures" as much as you think they do, especially potential clients. Dust yourself off, try again and have fun with it.

Advice for young professionals considering agency ownership?

I'd recommend looking beyond the big firms. There are many small, independent agencies where owners don't have a succession plan in place. These can be incredible opportunities to learn, grow and eventually take ownership. If the numbers make sense and the fit feels right, it could be a fantastic path to explore.

There's a lot of private equity buying out smaller firms these days, but I believe that having more independent agencies like ours benefits customers and the community. So don't overlook those smaller opportunities—they can be just as rewarding, if not more so.

Will Jones is IA editor-in-chief.