News Summary
Cindy Hesterman has made history by becoming the first female CEO of Vistage Florida, an organization dedicated to empowering business leaders. Appointed in 2022, Hesterman stood out as the only woman among 13 candidates. Her leadership aims to double Vistage Florida’s size while promoting values of kindness and integrity. With nearly 50 chairs serving companies generating around $50 billion in revenue, Hesterman’s journey exemplifies resilience and commitment to fostering a supportive culture for executives amid changing business landscapes.
Tampa, Florida – Cindy Hesterman has made history as the first female chief executive officer of Vistage Florida, an organization that focuses on helping business leaders enhance their effectiveness and success. Appointed in 2022, Hesterman was uniquely positioned for the role, as she was the only woman among 13 candidates considered for the top position. Her promotion marks a significant milestone in the organization’s history, which has traditionally been male-dominated.
In her new role, Hesterman oversees 66 groups composed of almost 50 chairs, serving companies that collectively generate nearly $50 billion in annual revenue and employ over 111,000 individuals. Her aspirational goal involves almost doubling the size of Vistage Florida while fostering a culture grounded in kindness, humility, caring for others, and curiosity.
Through her leadership journey, Hesterman has remained focused on values that resonate with her identity, citing faith, family, and service rather than chasing titles or accolades. She has openly discussed the struggles she faced during her early career, a time when women were often excluded from networking opportunities associated with certain business clubs and golf courses in Tampa. Hesterman encountered challenging work environments, including a boss notorious for making employees cry, which she navigated by refusing to internalize negativity. Another experience with a boss who misused team members for personal errands prompted her to reassess her professional landscape and make conscious decisions about her career direction. Hesterman advocates for the importance of maintaining one’s integrity and core values in any work-related situation.
Significantly, Hesterman became a chair for Vistage while balancing a successful career and personal life. After 18 years of marriage, she had her daughter, which influenced her decision to seek work-life flexibility as a priority. Her daughter has been involved in Hesterman’s professional life, attending Vistage retreats during her childhood and developing a sense of pride in her mother’s accomplishments.
As a newly appointed CEO, Hesterman advises executives to focus on their strengths and explore ways to apply them in varying contexts, particularly in light of uncertainties that have pervaded industries since the COVID-19 pandemic. The shifting landscape of business expectations has made it challenging for executives to formulate plans, underscoring the need for adaptability and resilience in leadership capabilities.
A turning point in Hesterman’s career came during a transformative exercise in the early 2000s, which solidified her self-awareness as a caring leader with the destiny to impact others positively. Since taking her position at Vistage Florida, she has engaged with business leaders through events such as TBBW’s “CEO Connect” series. This initiative aims to foster networking and meaningful discussions among top executives within the Tampa Bay region, combining cocktail receptions with insightful interviews featuring noteworthy CEOs.
Hesterman’s recent recognition as “Ms. May 2025” for a local publication has brought her further into the spotlight and garnered attention on various social media platforms, including LinkedIn and Facebook, boosting her profile as a role model for aspiring female leaders.
Vistage Florida is part of Vistage Worldwide, which boasts 45,000 members across 40 countries, aimed at empowering business leaders through peer support and coaching. As Hesterman steers Vistage Florida into a new chapter of growth, she remains committed to cultivating a legacy rooted in service to others, thus positioning the organization to meet the evolving challenges faced by companies today.
Deeper Dive: News & Info About This Topic
HERE Resources
Tampa Bay Business Leaders Gather for CEO Connect Event
Additional Resources
- Vistage Florida
- Wikipedia: Female Leadership
- Forbes: Importance of Female Leadership
- BBC News: Business Leadership Trends
- Tampa Bay Times: Vistage Florida Appoints First Female CEO
- Google Search: Business Leadership Trends 2023
Author: STAFF HERE TAMPA WRITER
The TAMPA STAFF WRITER represents the experienced team at HERETampa.com, your go-to source for actionable local news and information in Tampa, Hillsborough County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as Gasparilla Pirate Festival, Florida State Fair, and Tampa Riverfest. Our coverage extends to key organizations like the Tampa Bay Chamber of Commerce and United Way Suncoast, plus leading businesses in healthcare, finance, and technology that power the local economy such as BayCare Health System, Grow Financial Federal Credit Union, and KnowBe4. As part of the broader HERE network, including HEREJacksonville.com, HEREOrlando.com, HERESTPetersburg.com, and HERETallahassee.com, we provide comprehensive, credible insights into Florida's dynamic landscape.
