But to understand just how much Taylor has accomplished, one must recognize that her journey in the insurance industry was—like it is for so many of its most successful professionals—unintentional at the start.

Mother knows best

Nearly 60 years ago, in 1957, Taylor's grandfather, J.M. Wilkinson, was working as the manager of a small local bank in White House, a town of about 2,000 people at the time. He realized that he could better service his clients by packaging mortgages and Homeowners' insurance, and the Wilkinson Insurance Agency was born.

(Image: Shutterstock)

Three years later, Taylor's parents, Joe and Sue, joined the agency as co-partners. The three continued to work together until J.M.'s death in 1965. Taylor's parents bought his shares and became the sole owners.

“My mother was basically a pioneer in the '60s, being the woman principal of an insurance agency,” Taylor notes. Indeed, armed with only a high school diploma, Sue was quite the entrepreneur. “My parents owned three or four businesses at that time—a hardware store, an insurance agency and a residential and commercial real estate business,” Taylor recalls. “Everybody in town knew us.”

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Consequently, Taylor says her mother was often missing during dinner—”We ate a lot of bologna sandwiches,” she recalls—while she and her three younger siblings were growing up; Sue would attend night school at the University of Tennessee and take accounting and other business classes so she could better manage her companies.

“But my dad supported her 100%, and worked just as hard as she did. He also worked as a rural mail carrier,” she adds.

From Sue, Taylor received an early education on not only juggling a professional and personal life, but also valuable lessons in what it means to be independent and how to think critically—and how to be confident while doing it. “When I was about 11 years old, I had braces on my teeth and my orthodontist was in Nashville,” she recalls. “My parents were working six or seven days a week, and my mother said she could only take me to Nashville once—when I got my braces on. Every other time, I'd have to go by myself on a Greyhound bus. So she took me to the bus station and showed me a map. And I did it, because my mother said I could.”

So when Sue asked Taylor to join the agency in 1977, just a few months after her graduation from Middle Tennessee State University, Taylor was confident that she could handle the job—temporarily, of course, while she looked for a different position tailored to her skills in marketing and public relations.

Taylor was hired as a customer service rep, and quickly learned how to make deposits, rate policies and speak with clients. At the time, the agency was taking in about $200,000 in premiums (of which 75% was personal lines) and had just one other employee besides her and her mother.

As it does for so many in the insurance business, the bug bit and Taylor advanced to agency principal. “I came to work on April 1, 1977, and I received my insurance license around May 15 or the first of June,” she says. Two years later, she earned her CIC designation—and in so doing, became the first woman in the state of Tennessee to become a Certified Insurance Counselor. Taylor also holds Certified Professional Insurance Woman, Certified Professional Insurance Agent and Diversified Advanced Education accreditations.

About 18 months after Taylor joined the agency, “My mother went home for lunch so she could manage things related to her new-house construction, and she never came back to the office.” Sue's dream, Taylor would later learn, was to further develop her family's real estate business.

In 1990, Taylor became the sole owner of Wilkinson Insurance Agency, and has overseen its growth to five employees and $4 million in premium volume. Commercial lines have grown to represent about 40% of the agency's total, with much of that attributed to small commercial, farming and Contractors' insurance.

Hard work pays off 

Taylor credits agent associations for helping her adopt the skills that contributed toward her agency's growth, particularly the National Association of Professional Insurance Agents (PIA). “I own a small-town agency,” she notes. “I need to network with other people and have avenues for education. I've been in business for 38 years, and have met people across the state.”

In 1994, she won the PIA of Tennessee Agent of the Year Award, which commended her education, experience, contributions to the American agency system, and PIA board service and event participation.

“June brings great joy to whatever she does, a quality that is infectious,” says Mike Becker, executive vice president and CEO of PIA National. “This is something that has served her well in her small community, but would also help her succeed if she were an agent in midtown Manhattan. June is the quintessential Main Street professional insurance agent. She is a great leader in her agency and in representing her state within the PIA organization.”

Taylor also received the 1989 PIA of Tennessee Committee Chairperson of the Year award, and the 1993 and 1997 AAMGA Association Achievement awards. In 2007, she was named Tennessee Businessperson of the Year by the Future Business Leaders of America-Phi Beta Lambda.

“That's what gives me the satisfaction of coming into work every day,” she says. “With those recognitions, I still feel like I am giving to other people in the industry and my community.”

As a resident of the Volunteer State, it's only fitting that Taylor would hold a variety of leadership roles with agent associations and the local community. She currently serves as the national director for the PIA of Tennessee, an elected position she has held since 2006. Taylor also served the National Alliance on its CIC Board of Governors from 1991 to 1997, was named local president for the National Association of Insurance Women in both 1986 and 2007, and just finished her term as the national president of the American Insurance Marketing & Sales Society.

“I like being in business for myself,” Taylor says. “I prefer to be my own boss and I like making decisions—and there have been some that I regret. But I've had to live with them and learn from my mistakes. I tell young people, 'There's no perfect job, nor a perfect career, but 99% of the time, I don't regret this.'”

Taylor's speech resonated with at least one young person—her 26-year-old son, Andrew, who now works for his mother's agency as the personal lines CSR. The plan is for Andrew to take over someday as an agency principal and owner—but after he's works his way through other agency positions first, as his mother did.

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'All we do is work'

Besides Andrew, Taylor's family includes her son, Ben, a member of the Tennessee National Guard, and her husband, Gene, a retired metro Nashville firefighter.

“I raised my kids how I was raised,” Taylor says. For her boys, seeing both parents working constantly was part of their childhood. The two boys would walk to the agency after school and do homework and watch TV until it was time to go home, just as she did.

Taylor points out that it is possible to balance work and home life—with a caveat. “I don't sew, and I'm not a great cook,” she says. “My interests are somewhere else. And while raising young children, it was hard to leave them at night if I had client or association meetings. They got pushed over, which tore at my heartstrings. But my family benefited from those decisions.”

However, in the insurance business, “I've always said that it's harder to be young than to be female,” Taylor stresses. She doesn't recall ever being discriminated against because of her gender, but can recall instances in which underwriters who came to her office for a face-to-face early in her career were surprised by her age; one even told her she had the “voice of an old woman.” But Taylor says she doesn't mind it now, as that happened back in the '70s—and she adds that she needed to establish her expertise first, and not risk being pre-judged for being inexperienced.

Women in the insurance industry need to develop their education to get on an even level with their male peers, says Taylor. And she's not just talking about product knowledge: She wants to see women join associations and attend classes to develop leadership, interpersonal, technology and selling skills.

“When I speak with women in the industry who are in high-level positions, their story isn't that much different than mine. To get to this level, you have to be willing to work really hard,” she says, while also acknowledging that she may have been the beneficiary of opportunities that others don't have, due to working at a family agency and being in a small town. “But my parents, they taught me that all we do is work.”

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