Transformation at Vistage Florida has been intentional. Cindy Hesterman, chief executive officer of Vistage Florida, is guiding renewal that strengthens infrastructure, elevates experience and positions the organization to scale with integrity.
Hesterman leads a growth plan rooted in people, process and place. The company expanded its team with a full-time recruiter and leadership for operations and chair development, so new colleagues begin with structure and support. Engagement with chairs deepened through regular collaboration and journey maps that guide recruitment, onboarding and ongoing development. Technology upgrades improved the member experience and reinforced a refreshed strategy, strengthening the brand across Florida.
Hesterman also pointed the compass toward underserved markets. Strategic expansion in those communities brought tailored programming and collaboration that amplified impact. The approach blends innovation with partnership, showing how targeted development can lift leaders and strengthen regional economies. Every initiative ties to a simple outcome: better support for Florida’s chief executive officers and executive leaders today and into the future.
The future of work at Vistage Florida centers on human connection supported by smart tools. Hesterman treats innovation as an enhancer, not a replacement for the nuance, empathy and authenticity that great communication requires. Members, chairs and staff build digital fluency through training, mentorship and curated resources without losing independent thinking. The organization cultivates higher-level problem solving, emotional intelligence and adaptive leadership so the community stays prepared for an evolving world of work.
Personal energy starts with purpose. Hesterman reignites passion by staying close to the transformation of members and chairs, celebrating breakthroughs and keeping stories at the heart of the culture. Time with chief executive officers and field leaders informs strategy. Curiosity is encouraged, success is shared and mission alignment remains visible. She frames leadership as service—empower, listen and light the way—so people feel equipped to do their best work.
Her entrepreneurial path began outside the organization. Hesterman built a successful career in accounting and corporate leadership, then felt called to invest in leaders through peer advisory work. Years later the board sought a new chief executive. After a competitive process she was selected from 13 candidates, becoming the company’s first female chief executive officer. The charge was clear: Honor the community’s heritage and build a durable platform for the next chapter.
Vision for the next chapter is crisp. Vistage Florida aims to be the premier resource for chief executives across the state with strong outcomes, a trusted brand and deep relationships with every stakeholder. Members will credit the organization with advantage over their competitors because they find clarity, accountability and growth inside their groups.
A Titan 100 Honoree, Hesterman is known for a commitment to helping others become their best. Her service extends beyond business through the mission and vision board of Christ the King Lutheran Ministries. During more than two decades as a chair, she invested in leaders across the state and helped open new markets. The throughline never wavers—develop leaders, elevate communities and do the work with purpose, learning and impact.
