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Leader Spotlights
In-depth profiles celebrating the journeys, lessons, and lasting community impact of Southwest Florida's most transformative nonprofit leaders.
Dr. Margaret Calloway
President & CEO, United Way of Lee, Hendry & Glades
Margaret Calloway never planned to lead one of Southwest Florida's largest nonprofit organizations. Growing up in rural Georgia, she watched her grandmother organize community meals for families who couldn't afford groceries — a quiet, persistent act of service that planted a seed she wouldn't fully understand until decades later.
After earning her doctorate in public administration from Florida State University, Margaret spent twelve years in county government, rising to deputy director of social services in Lee County. It was there, in the gap between policy and people, that she discovered her calling.
"I kept seeing the same families cycling through the same systems," she recalls. "We were treating symptoms, never causes. I knew someone needed to bridge the gap between government resources and the organizations on the ground actually doing the work."
"True leadership is not about the title on your door — it's about the lives that change because you chose to show up every single day."
— Dr. Margaret Calloway
Leadership Lessons
In 2018, Margaret took the helm at United Way of Lee, Hendry & Glades — and immediately faced the devastation of Hurricane Michael. What could have been a crisis of leadership became her defining moment.
"The hurricane taught me that leadership isn't about having all the answers," she says. "It's about having the courage to say 'I don't know' and the humility to listen to the people closest to the problem."
Under her stewardship, the organization raised a record $22 million in 2024, expanded early childhood programs across underserved communities, and launched a groundbreaking workforce development initiative that has already placed 1,400 individuals into living-wage careers.
Her three principles of leadership:
First, radical transparency — she publishes every financial decision and strategic pivot in real-time to her board and community partners. Second, proximity — she spends two days a month visiting frontline programs, sitting with families, and listening. Third, succession — she has built a leadership pipeline that has produced four other nonprofit CEOs in the region.
Community Impact
The numbers tell part of the story: $22 million raised, 50,000 children served, 1,400 careers launched. But Margaret measures her impact differently.
"When a mother tells me her child can now read at grade level because of a program we funded — that's my metric. When a veteran walks into our workforce center and walks out with a job offer — that's the return on investment I report to my board."
Her influence extends far beyond her own organization. As architect of the region's first Collective Impact Coalition, Margaret has unified 47 nonprofits around shared goals in education, health, and economic mobility — breaking down silos that had persisted for decades.
The coalition's model has been studied by the Aspen Institute and is being replicated in four other regions across the country. For Margaret, it's the ultimate validation of her grandmother's philosophy: when you feed the community, the community feeds itself.
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CEO, Everglades Foundation
How a former marine biologist turned his passion for Florida's waterways into a billion-dollar environmental advocacy movement.
Isabella Reyes-Fuentes
Founder & CEO, Horizon Community Health Alliance
Building a healthcare safety net for Southwest Florida's most vulnerable — one clinic, one patient, one community at a time.
Isabella Reyes-Fuentes
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