Taylor Clevenger: Leading, Learning, and Inspiring at Oakhill

At Oakhill Day School, we are fortunate to have educators and leaders who are deeply committed to innovation, growth, and the success of our school community. One such leader is Taylor Clevenger, an Oakhill alum (Class of 2012) whose journey has come full circle—bringing his passion, creativity, and strategic mindset to every aspect of school life.

This year, Taylor was invited to present at the 2024 National ISACS (Independent Schools Association of the Central States) Conference in St. Louis, joining fellow Oakhill educator Audra Olson on the national stage. Taylor’s session, How to Cultivate the Best Summer Ever, was a hands-on, high-energy workshop that had attendees up on their feet, actively engaging in discussions about the power of summer programming. Drawing on his experience in building and growing Oakhill’s summer programs, Taylor shared insights on how independent schools can create dynamic, mission-aligned summer offerings that serve both students and the school’s financial sustainability. Using skills gained from attending Disney’s renowned leadership program, Taylor encouraged schools to dream big while keeping families at the heart of every decision. His passion, energy, and strategic vision left a lasting impression on educators from across the region.

But Taylor’s impact at Oakhill extends far beyond his work in summer programming. Over the years, he has worn many hats—beginning as a TA in Kids' Club, assisting in PE, and working his way up to roles such as Director of Edupreneurship and Director of Auxiliary Services. Today, as Assistant Head of School for Non-Academic Affairs and Athletic Director, Taylor plays a critical role in shaping the future of Oakhill. From overseeing budgeting and strategy to ensuring the school remains fiscally responsible while continuing to dream big, Taylor is a driving forcebehind Oakhill’s continued success.

His leadership is also deeply rooted in fundraising and advancement, where he has helped grow the school’s development efforts, bringing Oakhill closer to its financial goals. And, as if that weren’t enough, Taylor devotes countless hours to expanding Oakhill’s athletic programs, all while serving as a dedicated coach and mentor to student-athletes.

Taylor is a visionary leader, always eager to learn, grow, and inspire those around him to think outside the box. His ability to balance strategy with creativity, big-picture thinking with attention to detail, and school tradition with innovative new ideas makes him an invaluable part of Oakhill’s leadership team.

We are proud of Taylor’s continued contributions to Oakhill and the broader independent school community. Please join us in celebrating his achievements and the incredible impact he has on our students, staff, and families!

See Taylor in action!