Cindy Hesterman didn’t always know she would become a leader of leaders. She was the daughter of a janitor and an accounting clerk, born in Fort Wayne, Indiana, during a time when hard work was expected, and excess was unheard of. But what she lacked in material wealth, she gained in purpose rooted in faith, humility and a deep sense of right and wrong.
Today, as the chief executive officer of Vistage Florida, the first-ever female to hold the role, Hesterman guides some of the state’s top executives through their toughest decisions and biggest milestones. Her journey to the corner office wasn’t a straight path. It was built on decades of grit, service and a bold refusal to be anyone but herself.
“I’ve learned that my voice matters,” says Hesterman, reflecting on the early experiences that shaped her as a woman, a leader and a mentor.
That voice—quiet but resolute—has since helped hundreds of others find their own.
Fort Wayne Foundations
Hesterman was born to parents who were older than most. Her mother, Helen, had suffered three miscarriages before Cindy arrived, at age 41. Her father, Otto, was a school janitor with a deformed leg who walked with a unique limp after surviving childhood polio. Kids loved him—his jokes, his warmth—but Cindy, like many young daughters desperate to fit in, sometimes felt embarrassed by his visible difference.
“It wasn’t that I didn’t love him,” she says. “It’s just… I didn’t know how to be okay with being different.”
Still, it was Otto who taught her one of life’s earliest, most enduring lessons: never let anyone tell you what you can or can’t do. Doctors had told him he would never walk and he proved them wrong. He expected nothing less from his daughter. He was confident enough to talk to anyone, even the superintendent of schools, because as he would say, “He puts his pants on one leg at a time, too,” she remembers fondly.
The family didn’t have much, but they never went without. Meals were simple—Campbell’s soup stretched with extra water and a slice of bread or a few crackers. A trip to Kmart for an 88-cent submarine sandwich, split three ways, was a family treat. “We were poor in things, but rich in love,” she says. And I never knew we were poor, I just knew we had less than some.
Hesterman spent her childhood biking, playing “kick the can” in the alley and raiding the library for books she’d read under the covers with a flashlight. She didn’t have siblings, but found deep connection through her cousins, church and neighborhood friends. From an early age she was independent, thoughtful and drawn to leadership—even if she hadn’t realized it yet.
In fifth grade, a gym teacher noticed her speed during a 50-yard dash on a gravel alley behind the school. She ran faster than anyone, even the boys, surprising everyone, including herself. She would go on to set a school record in the 100-yard dash in high school (a record, she likes to point out, that “still stands,” thanks to the later switch to measurement in meters).
Her childhood wasn’t without fear. As middle school approached, and racial tensions escalated into violence at the local public school, her parents made the difficult decision to send her across town to a private church school. There was only one car in the family, so Hesterman took a public bus—sometimes in the snow, always alone—making transfers downtown to get to class.
She flourished in her new high school, participating in nearly every club and activity possible, from National Honor Society and track to band, handbell choir and leadership roles.
After an off-field ankle injury put a damper on her track trajectory, she went on a band tour with her school during which she rode on a nine-hour bus excursion. It was on that ride she met her husband, Eric. “One door closed,” she says. “Another opened.”
A Mind for Numbers and a Heart for People
Hesterman didn’t grow up imagining a career in business leadership. But, from a young age, she knew how to work hard. After graduating near the top of her high school class, she chose to stay in Fort Wayne, for college, attending Indiana University-Purdue University Fort Wayne, a local commuter school with affordable tuition. There were no dorm rooms and no campus life to speak of. But there was opportunity and that was all she needed.
She worked full time while also carrying a full course load, paying her own way through school with a mix of scholarships, babysitting money, retail wages and sheer willpower. “Sleep wasn’t really part of the plan,” she laughs. “I was just trying to get through.”
Even with her packed schedule, she still found time to lead. She joined a business fraternity, served as president of the Accounting Society, and became known for her sharp instincts and even sharper pencil. Her husband, Eric—whom she had married during college—worked two jobs, while she juggled coursework and retail management.
“We didn’t have much, but we made it work,” she says. “Garage sales furnished our first home. We decorated our stereo at Christmas instead of a tree. But it was ours.” She was no stranger to a home full of love instead of “stuff.”
After college graduation, Cindy took a job at Coopers & Lybrand, in Tampa, one of the country’s top accounting firms, at the time. It was a prestigious opportunity—but not an easy one. The Tampa office of the firm had no female partners and the path for women was narrow and rocky. She recalls being questioned for wearing a jacket dress instead of a traditional navy-blue suit. “Is that a suit?” a partner asked, skeptically. “Well, it’s a professional outfit, it’s a jacket dress” she replied. “And I’m going to wear it.”
Sexism was embedded in the business culture everywhere at the time. In one corporate job, a male executive grabbed her inappropriately on the dance floor at a holiday party, in front of her colleagues. At another, she was repeatedly berated by a volatile boss who took pride in making people cry.
“He once screamed at me in front of everyone in the office, asking what kind of parents could raise an idiot like me,” she remembers. “I just stared at his ear and thought about how big it might get as he aged,” she says laughingly. She refused to give him the satisfaction of tears.
Her resolve didn’t go unnoticed. Over time, that same manager came to respect her. So did many others. But the emotional cost of staying strong in those environments was steep. Hesterman began to understand how important culture—and kindness—was in the workplace. And she quietly started thinking about what kind of leader she wanted to be.
That vision sharpened, in 1995, when she was fired from a job for doing the right thing.
At the time, she was working for a large company and had helped structure a creative bonus plan for a team of road-warrior employees who had given up their homes and personal lives to help with acquisitions. When an executive suddenly backtracked on the agreement, Hesterman provided documentation showing the original terms and requested that the employees be paid, as was promised. The promises that had been made to those employees, in exchange for their loyalty to the company, was enough for Hesterman to stand up for what was right. Days later, she was publicly escorted out of the building without a clear explanation.
“I had never done anything wrong,” she says. “I was in shock. I thought, ‘Who’s ever going to hire me now?’”
She didn’t stay down for long, that isn’t her way. A managing partner from her old accounting firm referred her to a local company in need of a chief financial officer. The hiring executive—Jeff Huenink—was a member of a leadership group called TEC, short for The Executive Committee. Huenink insisted Hesterman join the program. “Trust me,” he told her. “You’ll love it.”
He was right. TEC (which would later become Vistage) gave her more than just professional development. It gave her clarity. She wasn’t just a numbers person. She was a people person. And helping others grow was where she truly shone.
The Making of a CEO
By the early 2000s, Hesterman had built a solid career in finance. She was working as an executive for a growing company, in Tampa Bay, traveling frequently and managing the intricacies of rapid growth. But something about the grind didn’t feel quite right anymore, especially after the surprise arrival of her daughter, Ashley, when she was 39.
“It was a total shock,” Hesterman says. After 18 years of marriage, she and Eric had long given up on the idea of having a child. But there she was, pregnant in the middle of a major corporate transition. “I had no clue what I was doing, but I knew I didn’t want to miss a thing.”
Motherhood gave her a new perspective. The long hours, the frequent travel—it wasn’t sustainable. And she knew she had more to offer than spreadsheets and budgets. She started thinking back to something that had happened years earlier, during a TEC meeting.
At the time, she was a member of a TEC “key group” made up of second-in-command executives. When she faced a big decision—whether to move to Boston for a corporate opportunity or stay in Florida, she brought it to her group. Members offered all kinds of advice, but two of them said something unexpected: “You should be doing this. You should be running groups like these.”
At the time, she brushed it off. She wasn’t a CEO. She didn’t have a sales background. She wasn’t at all sure she could do it, let alone if she wanted to.
But after Ashley was born, and she began craving more purpose and flexibility, those words came back to her. She called her former TEC chair, Chip Webster, and asked, “Do you really think I could do this?”
Without hesitation, he said yes.
In 2002, she built her first Vistage group. She had some part-time consulting work to support her while she built her practice, but she jumped in with everything she had.
“I wasn’t sure what I was doing,” she says. “But I knew I loved helping people get unstuck. I loved watching lightbulbs go off. I loved asking questions that made people think differently.”
It was the perfect fit. Over time, she grew her chair practice to four groups—working with CEOs, key executives and emerging leaders from across Tampa Bay. She coached them one-on-one, facilitated monthly meetings and built a community of confidentiality, trust and accountability. Some members stayed with her for years. Some sold their businesses for more than they ever thought possible. Some, she says, simply learned how to have a life again.
“One member told me, ‘I just want to know my kids. I’ve missed everything,’” she recalls. “We worked together to change that. Eventually, his wife told me, ‘He is never allowed to leave this group. I have my husband back.’ That meant everything to me.”
The stories piled up—turnarounds, transformations, breakthroughs. And so did the recognition. In 2004, Hesterman received the TEC International Chair of the Year Award. In 2013, she was honored with the Red Scott Award, named after one of her mentors and the highest honor in Vistage Florida
But even with her success, she never sought the spotlight. Her focus remained on the people in front of her—the business owner facing burnout, the executive wrestling with imposter syndrome, the founder contemplating a legacy. Her coaching wasn’t about giving answers. It was about helping people find their own.
In 2022, after 20 years of chairing groups, she stepped into a new role: chief executive officer of Vistage Florida, which is projected to have revenue of more than $13 million, in 2025.
She was the only woman among 13 candidates—and became the first woman ever to hold the top spot in the organization’s history.
The transition wasn’t without its challenges, said Hesterman. “I went from being a peer to being the boss,” she says. “That changes the dynamic. I had to learn who was telling me what they thought I wanted to hear rather than the candor I sought and how to lead in a different way.”
She brought her signature, servant leadership style into the role and leaned into her experience. When major hurricanes swept through the state, she prioritized support for chairs and members in affected areas. She refocused the organization on connection, accountability and growth.
And in a full-circle moment, she joined her own Vistage group—this time in Atlanta. “My Florida chairs are my customers,” she explains. “I needed an independent sounding board too.”
Living with Purpose
Through Hesterman’s professional achievements, her identity has never been rooted in titles or accolades. Her truest compass has always pointed toward faith, family and serving others.
Hesterman and her husband, Eric, have built a life grounded in love, mutual respect and what she calls “creative problem-solving.” They married young—she was 21, he was 20—and from the beginning, they did whatever it took to make things work. As they grew up together, they learned to laugh through the lean seasons.
“He’s my soulmate,” Hesterman says, simply. “We’ve been through everything together. We’ve supported each other through every twist and turn.”
When their daughter, Ashley, arrived late in life, she became a joyful surprise and the center of their world. Hesterman adjusted her career to be more present. The flexibility of her Vistage chair role allowed her to pick Ashley up from school, be involved in her life and show her, day by day, what purpose-driven leadership looked like.
Hesterman’s heart for service runs deep. It was modeled for her by her grandmother, Bertha, a woman of quiet strength and sacrificial generosity. During the Great Depression, Bertha would invite hungry strangers into her home and share whatever food she had, even if it meant less for her own family. She never judged. She simply gave.
“She was my hero,” Hesterman says. “She lived her faith. She treated everyone with dignity and she truly listened. That’s the kind of woman I strive to be.”
While her professional life has always been busy, she’s remained intentional about giving back. She’s volunteered with organizations like Habitat for Humanity, Paint Your Heart Out and the Homeless Empowerment Program. These days, her heavy travel schedule makes hands-on volunteering more challenging, but she’s made it a priority to build a culture of service at Vistage Florida. Every year, her team selects at least two charitable projects to support—like the time they built an outdoor playhouse for a child with cancer.
She also gives, generously, often anonymously, to causes she believes in: her church, local nonprofits and organizations supporting children, families and underserved communities. “We’ve been blessed,” she says. “And we believe in giving back.”
Hesterman is also deeply committed to mentoring women—especially those navigating leadership roles in male-dominated industries. Over the years, she’s guided countless female executives, helping them negotiate deals, prepare for exits or simply believe in their own potential. She recalls one client who initially ignored an offer to sell her business. Hesterman encouraged her to have the conversation anyway, to protect her client list and stay open. Within 90 days, the woman sold the company for more than twice what she expected.
“She might not have taken the call without that push,” she says. “Sometimes women just need someone to say, ‘You’re ready. You’re enough.’”
Though her calendar is packed with meetings, strategy calls and travel, she still ushers at her church and serves on the board of ACG Tampa Bay, a nonprofit that supports dealmakers and business leaders. It’s not about adding lines to a résumé. For her, it’s about staying connected to her values—and using her talents to lift others up.
“I believe we’re all here for a reason,” she says. “I just try to live in alignment with that, every day.”
Legacy and Leadership
Ask Hesterman what it means to be a leader and she won’t mention titles or power. She’ll talk about service. About lifting others. About knowing when to speak and when to simply listen.
“I’ve learned that my voice matters,” she says. “And I want others—especially women—to know that theirs does, too.”
That belief has guided every chapter of her life, from the young girl in hand-me-downs navigating a public bus across town, to the trailblazing executive who now leads one of the most influential business leadership organizations in Florida. She has never forgotten where she came from—or who helped her get here.
Her “Big Hairy Audacious Goal” (as Vistage leaders called it) was once just a quiet dream: to someday become CEO of Vistage Florida. She shared that goal with a fellow female chair, back in 2003, never imagining it would come true. In 2022, when she was named CEO, that same colleague reminded her: “You did it.”
It wasn’t luck. It was decades of preparation, growth and courage to stand firm in a world that often asked her to shrink. She never shrank. She showed up. She led. And she helped others do the same.
“Helping people find whatever it is they’re trying to achieve—and watching them get there—that’s what drives me,” she says. “To know I had anything to do with that. That’s just … really cool.”
