In 2022, after 20 years of chairing groups, Cindy Hesterman was named chief executive officer of Vistage Florida. She was the only woman among 13 candidates and is the first woman to hold the top spot in the organization’s history.
Through her professional achievements, her identity isn’t rooted in titles or accolades. Her truest compass has always pointed toward faith, family and serving others.
Bridgette Bello, publisher and CEO of Tampa Bay Business and Wealth, interviewed Hesterman in front of a live audience, at Five Labs, in Tampa. This transcript is edited for length and clarity.
What has it been like being Ms. May 2025 for TBBW?
The cover came out at the beginning of the month, and I’ve been on the road for 11 of the past 13 days, so it’s been interesting. I’ve heard from people from around the world who saw the post on LinkedIn or Facebook, some people I, sadly, don’t even remember, but they remember me, which is kind of fun. It’s been quite an honor. I don’t see Hugh Campbell here, but I wished him a happy birthday, and he said, “Thank you, Cover Girl,” which was just kind of cute.
Part of what you and I really enjoyed talking about were stories, some difficult ones. How do you handle difficult situations in your professional life?
When I first started my career, in Tampa, you couldn’t go to some of the business clubs downtown because women weren’t allowed. You couldn’t play at certain golf courses because women weren’t allowed. And it seemed like all the parties and celebrations were at the Tanga Lounge, which was like the tamer version of Mons Venus. I chose not to participate, for obvious reasons.
There was the boss who yelled, [and] his claim to fame was making everyone cry and he would brag about that. I would think, “Oh my gosh, you are never going to make me cry.” So, I prepared myself: I’d focus on his ear and think about how big it would get as he aged, or what I was making for dinner, or my weekend plans — distractions helped.
Another boss, and this didn’t make the story, wanted me to have my team come in on the weekend to help him with some stuff at his home, personally. I said, “That’s not really appropriate,” and he replied, “Just be more of a [rhymes with itch] and they’ll do it.” I knew I wouldn’t stay in that role much longer. But the point is we have choices. We can’t always control what happens, but we can control how we respond. I chose to maintain my integrity, my core values and to stand firm.
In May we celebrated Mother’s Day. Tell us how becoming a mom impacted your leadership style.
I had a lot of friends who had babies earlier. Eric [Hesterman’s husband] and I have been married for 43 years and our daughter turns 25 this year. We were married for 18 years first. It just wasn’t happening for us and then it did. I knew I needed to work, but I also wanted to be a mom. That’s what prompted me to become a chair [for Vistage]. I wanted more flexibility.
It was a challenge, but fun. My daughter would tell her teachers about what I did, “Mommy takes a briefcase to work and I’m really proud of her.” She’d come with me on Vistage retreats and help me with toys on tables and beach games. One time she told her teacher, “My mommy plays with toys, eats candy and plays games on the beach.” The teacher wanted to meet me and later told me, “I want to do whatever it is that you do.” That was fun. As an adult, my daughter has told me she appreciated that I worked and was a role model.
You have access to literally thousands of executives. What’s keeping them up at night?
In general, it’s uncertainty. It’s hard to plan when things keep changing. It’s a bit like COVID, except during COVID everyone was impacted. Now, some industries are thriving — like a member who runs an aluminum extrusion company doing great due to tariffs — while others are being shut down. It is that uncertainty that’s creating the most stress.
When you’re chairing a group, how do you help executives navigate that uncertainty?
I try to refocus them on what they do well. When in doubt, go back to your strengths. Ask: where else can I apply this strength? What other industry, product or service could it support? Can I grow by acquiring another company? I believe in focusing on strengths, that’s where people really grow.
One thing we didn’t include in the story is an exercise you went through in the early 2000s to identify your identity and destiny. Can you share that?
I did it as a favor to a friend who was leading a nine-week, Christian-based class. It ended up taking 12 weeks. There were assessments, journaling and prayer. I was worried I’d find out chairing wasn’t my destiny. But I learned my identity is that I’m a trusting and caring leader. My destiny? To lead leaders and impact many more.
I resisted the idea of doing more. I had four groups, I was a mom, a wife, I didn’t think I could do more. Then I became CEO. Now I have 66 groups, almost 50 chairs reporting to me and we’re still growing. I’m on a magazine cover, speaking in front of thousands. I think this is my destiny.
Let’s talk about Vistage’s size and impact.
Vistage Florida member companies generate almost $50 billion in annual revenue and employ more than 111,000 people. We’re affiliated with Vistage Worldwide, which has 45,000 members in 40 countries. We’re less than 2% of the global organization, so the global revenue impact is massive. Business supports people and we play a big part in that.
OK, now something fun. What would surprise people about you?
My daughter, Ashley, and I do “Just Dance” on the Wii. Eric even joins in. That’s our fun family activity. Not sure it’s a hidden talent, though. I used to be pretty good at water skiing. Haven’t done that in a while!
What’s your new BHAG [Big Hairy Audacious Goal]?
To almost double the size of Vistage Florida.
Final question: What do you want your legacy to be?
I’d love it to be about kindness, humility and caring for others, not divisiveness. Curiosity, too. I’ve learned that if I ask the right questions and stay curious, I understand people better. That’s how I want to be remembered.
ABOUT ‘CEO CONNECT’
TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. M.E. Wilson, Hyde Park Capital and Kuducom were presenting sponsors. The host sponsor was FIVE Labs. TBBW’s video partner is Empowering Creative.
The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.
Partnering with TBBW provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.
For information about event sponsorship opportunities, email Jason Baker at [email protected].