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Advice / Career Paths / Training & Development

This Manager Has Worked in Insurance for More Than 40 Years—Here’s Why She Stays

Michelle Wildman, a regional managing director at Navigators, a brand of The Hartford
Michelle Wildman, a regional managing director at Navigators, a brand of The Hartford.
| Courtesy of The Hartford

When Michelle Wildman began her career in insurance more than 40 years ago, business moved a lot slower. She relied on typewriters, paper files, and snail mail to get her work done. Of course, things have advanced a lot since then—and Wildman has stayed inspired throughout it all.

“Nothing stays the same in the insurance industry; there is constant change,” she says. “That means there are opportunities to learn something new every day.”

Wildman is currently a regional managing director for the Houston branch within the Primary Casualty department at Navigators, a brand of The Hartford. The company prides itself on encouraging its employees to continuously learn and grow. Since joining, Wildman has received immense support from her managers, which has helped her earn multiple promotions.

“Upper management encourages employees to take advantage of all the education and training that is offered,” she says. “More than anything, I have always been advised to take chances and get outside of my comfort zone. While transitioning to my current role, both my peers and managers have been so supportive. I know I can pick up the phone at any time and someone will be available to provide guidance.”

Here, Wildman shares how Navigators, a brand of The Hartford, prepared her for a leadership role, why she loves mentoring those who are new to the insurance industry, and the importance of being an active listener.

Why did you decide to pursue a career in the insurance industry?

When I moved to Houston, my sister was a marketing representative for an insurance company, and she told me about an entry-level position at an insurance agency. I was hired to file, type envelopes, invoice, and do other basic tasks, but was also offered various insurance classes. I realized quickly that the industry provided endless opportunities for advancement if I applied myself and took advantage of the training.

That’s the thing about the insurance industry: Not only are you exposed to on-the-job training, but there are also numerous classes and programs that companies and associations offer if you want to take advantage of them.


You worked at Navigators before it was acquired by The Hartford. How has the acquisition impacted you and your work?

When I heard we were purchased by The Hartford, I was nervous about what that meant for us. As it turns out, it’s made things better. Having the history and financial backing of The Hartford behind us has been a huge asset. In an industry where you have startups coming and going, we can always point to The Hartford’s stability in the market.

We now have access to better systems and resources such as The Hartford’s risk engineering department and claims specialists. The Hartford provides access to numerous training courses as well as a great benefits program. There are many opportunities for employees to expand their knowledge base and career development by exploring other departments, lines of businesses, and regions.

What are you responsible for in your role as a managing director?

I am responsible for leading the Central region of the U.S. in contributing to the overall financial success of the department. This involves communicating the goals to the team, monitoring the results, training new underwriters, mentoring those in training, keeping informed of market trends and competition, staying in close contact with our broker partners, and communicating challenges and successes to upper management. I also underwrite my own book of business, so I stay in tune with the day-to-day needs of the production underwriters on my team.

How has The Hartford supported and encouraged your career growth?

Along with a variety of online courses, I’ve had the opportunity to attend conferences that keep me up to date on current industry trends and are great for networking. I’ve been encouraged to participate in projects and work with others outside my region to research different topics related to our department and plan strategies.

I also participated in the LEAD program, designed for all new managers at The Hartford. It gave me a great opportunity to get to know my manager and to take advantage of the wide variety of experience represented in the program. The real-world interactions within the group provided a chance to discuss and brainstorm how to lead most effectively and gave me the confidence to navigate any situation. I felt those sessions were the most valuable lessons of the program.

What is the Emerging Underwriter Program? What was it like being a mentor in the program?

Underwriters perform a challenging task: They determine the risks involved in insuring a business and calculate a price for the coverage that works for both the customer and the insurer.

The Emerging Underwriter Program is a trainee program available to those who are new to the insurance industry and/or to underwriting. It covers insurance basics, underwriting knowledge, and specialty business specifics, and gives the participants hands-on experience with experts in the industry.

I was fortunate to be given the opportunity to mentor one of the participants who now reports to me as an underwriter. Watching someone develop and coaching them along the way has been one of the most fulfilling experiences of my career. Someone new in this career has a fresh set of eyes and can oftentimes offer suggestions on ways to improve. I learned a lot by looking at things from their perspective and their enthusiasm created excitement within the department.

What skills are necessary to succeed as a manager?

One of the most important skills is time management, and I focus on improving it daily. Prioritizing where to focus my attention and energy helps to keep me organized and deliver what my team and customers need.

I also think active listening is essential to being a good manager. I have found that listening to my team and asking for their input has helped me the most. In this industry there is no way for one person to have all the answers, so we depend on each other’s knowledge and experience. The team collaborates to solve problems by thinking outside the box. That’s one of the things that makes this job and career so interesting.

Why is now an especially exciting time to join Navigators, a brand of The Hartford?

Navigators, a brand of The Hartford, is one of the most stable and innovative companies in the industry. Our upper management has been supportive of our initiatives and goals and willing to provide the tools necessary to meet them. We are constantly looking for creative ways to solve issues within the industry. Being part of a large company like The Hartford also allows for countless opportunities to advance in your career and diversify your work experience.