Few people have influenced the development of insurance producers as profoundly as Diane Masterson. After more than 40 years in the industry, the former Alliance board member, Dynamics of Selling instructor, and co-founder of Elite Producer Program continues to shape the next generation of insurance professionals.

Interestingly, Masterson never planned on a career in insurance.

While attending college in Ohio, she accepted a customer service position with JCPenney Property & Casualty after another job opportunity unexpectedly disappeared. Later, she moved into underwriting, but even then, she was convinced insurance was temporary.

The turning point came during a conversation with her uncle, who criticized the insurance industry. As Masterson found herself defending the profession, she realized something important.

“I discovered that what we do really matters,” she explained. “We protect the things that are most important to people.”

That realization transformed a job into a calling.

Over the following decades, Masterson worked in underwriting, training, sales development, and agency education. Along the way, she helped create the highly successful Pacesetter sales development program and eventually launched Elite Producer Program, where she coaches new producers and agencies.

According to Masterson, many of the challenges facing new producers today are the same ones she observed 30 years ago.

“The hardest part is getting started,” she said. “Learning how to prospect, making those calls, and getting appointments remain the biggest hurdles.”

Her solution is a combination of proven sales processes and consistent coaching. For decades, she has incorporated the Alliance’s Dynamics of Selling program into producer development efforts, emphasizing the importance of understanding why buyers change insurance providers: price, coverage, service, or relationship.

Masterson particularly values the program’s diagnostic approach, which teaches producers how to qualify opportunities before investing time and effort pursuing them.

“Many salespeople don’t realize they have a choice about who they work with,” she said. “A good sales process helps producers gain confidence and control.”

Yet training alone is not enough.

Masterson believes coaching is what turns knowledge into action. Through regular one-on-one coaching sessions, she helps producers establish prospecting plans, track activity, improve specific skills, and overcome obstacles in real time.

“It makes the training real,” she explained. “People leave a class excited, but then they return to everyday life. Coaching helps them apply what they’ve learned.”

Perhaps the greatest reward comes from watching producers succeed. One former participant, Anna Reyes, initially appeared unlikely to thrive in sales based on assessment results. Through determination, hard work, and coaching, she became a top-performing producer and advanced to working on large commercial accounts.

For Masterson, stories like that define success.

“Everyone’s success is different,” she said. “You have to define what success means for you.”

Her final advice for anyone considering a career in insurance is simple: work hard, stay open to growth, and recognize that insurance can be an incredibly rewarding profession. As Masterson’s own journey demonstrates, sometimes the career you never expected becomes the one you love most.