Stepping Inside Oak Park: What CEOs Can Learn From Sarasota's Principals

Guest Correspondence

This past week I had the privilege of participating in the Sarasota school’s “CEOs in Schools” initiative—an experience that left me energized, humbled and even more convinced that some of the strongest leaders in our community are walking the halls of our public schools every single day. I had the honor of shadowing Principal Sean Donovan at Oak Park School here in Sarasota, a campus that quietly delivers extraordinary work for some of our most exceptional students.

Oak Park serves over 200 students, each with unique needs that require patience, creativity, and a level of compassion that can’t be taught in any textbook. What struck me immediately was the strength of the entire team—the teachers, support staff, therapists, specialists, paraprofessionals, volunteers, and of course, Principal Donovan himself. These are people who don’t just work in education—they pour themselves into it. They lift kids who need more than most and celebrate every win, big or small.

During my visit I toured classrooms, met with teachers, and spent time in the school’s impressive life-skills programs. Oak Park operates a fully functioning food pantry that serves families in need and a student-run coffee shop that teaches practical, hands-on skills—everything from customer service to managing money to working as a team. These aren’t “cute” add-ons. They’re confidence builders. They’re future-shapers. They’re the kind of real-world experiences that help students find purpose and independence.

For me, this wasn’t just a professional visit. It was personal. I’m a proud graduate of public schools, and both my mother and my mother-in-law were longtime public school math teachers. I’ve seen firsthand the sacrifices teachers make, the extra hours they give, and the heart they bring into classrooms. Walking through Oak Park brought all of that rushing back. It reminded me of the foundation that public education gave me—and the responsibility we all share in supporting it.

We should also be clear-eyed about just how special Sarasota’s school system is. In a state with 67 school districts, Sarasota is one of only two that maintain an A-rating. That doesn’t happen by accident. It takes rigor, partnership, innovation, and a culture of excellence—starting at the very top.

Superintendent Terry Connor deserves real credit for bringing new ideas into the district, including the “CEOs in Schools” program. By placing business and civic leaders inside classrooms, he’s creating a bridge of understanding between two worlds that have far more in common than many realize. At the end of the day, principals are every bit the CEOs of their campuses. They manage budgets, oversee large teams, navigate complex regulations, solve problems in real time, and answer to three distinct stakeholder groups—parents, students, and teachers. That’s leadership at its highest level.

My time at Oak Park reaffirmed something I’ve long believed: when our schools thrive, our entire community rises with them. These students, teachers, and families aren’t asking for applause—they’re asking for partners. And Sarasota has an opportunity to show what partnership truly looks like.

If you’ve ever wondered how to support our schools in a meaningful way, start by getting connected with the Education Foundation of Sarasota County. Under the leadership of Jennifer Vigne, the Foundation is doing some of the most innovative, student-centered work in the state—strengthening teacher resources, building college and career pathways, expanding mentoring, and ensuring students have the wraparound support they need to succeed. Jennifer and her team are always looking for community members who want to roll up their sleeves and help.

Whether you choose to volunteer, support classroom initiatives, or simply learn more about the challenges and opportunities inside our schools, your involvement matters. Every hour, every conversation, every investment makes a difference.

After spending the day at Oak Park, watching Principal Donovan and his team in action, I’m more convinced than ever that Sarasota is not just an A-rated school district—we are a community capable of championing excellence at every level. Let’s show up. Let’s stay engaged. And let’s continue to build the kind of educational ecosystem our children—and our community—deserve.

Heather Kasten is the President/CEO of the Greater Sarasota Chamber of Commerce. She holds a bachelor’s degree from the University of Iowa in Business Administration and an MBA from Webster University. She has served as President/CEO since 2019 and sits on the board of several nonprofits. Contact her at hkasten@sarasotachamber.com.

« View The Saturday Nov 22, 2025 SRQ Daily Edition
« Back To SRQ Daily Archive

Read More

 November is a Month of Gratitude

November is a Month of Gratitude

Christine Robinson | Nov 15, 2025

From Curiosity to Discovery: Science Comes Alive at SCF

From Curiosity to Discovery: Science Comes Alive at SCF

Tommy Gregory | Nov 15, 2025

Where Generosity Meets Opportunity

Where Generosity Meets Opportunity

Veronica Thames | Nov 8, 2025

As Season Returns, So Does the Power of Tourism in Sarasota County

As Season Returns, So Does the Power of Tourism in Sarasota County

Erin Duggan | Nov 8, 2025