After an extensive nationwide search, Out-of-Door Academy’s board of trustees has announced the appointment of Debra Otey as the next head of school, effective July 1.
The academy’s lower school is located on Siesta Key.
James Connor currently is serving as interim head of school for the 2021-2022 school year.

Otey was selected from a pool of impressive candidates after a thorough search process. The school’s advisory and search committees found Otey to be a dynamic, accomplished, passionate educator, and well-poised to lead Out-of-Door into its next chapter.
Tom Murphy, chairman of Out-of-Door Academy’s board of trustees, led the search committee through this process alongside Educators’ Collaborative, an executive search firm.
“As Out-of-Door prepares to celebrate its 100th anniversary in 2024, this transition of leadership creates a wonderful opportunity for our next head of school to guide us to new levels of academic, athletic, and artistic success while never forgetting our core values of respect, integrity, service, excellence, and responsibility,” Murphy said. “This search — for an individual of outstanding character and professional experience, demonstrated ability to inspire and encourage faculty, staff, students, and alumni, and support the forward momentum of the school’s growth — resulted in the appointment of Mrs. Debra Otey.”
Otey holds a Bachelor of Science in secondary education (English), a Master of Science in secondary education (English), and is currently completing an Ed.D. in educational leadership from the University of North Carolina at Wilmington. She has taught middle school English, and held positions as an elementary school principal, head of middle school, Assistant School Superintendent, and most recently as the Head of Upper School at Cannon School in North Carolina.
“I am excited to join a pre-K through 12 community that emphasizes character education and student well-being,” Otey said. “Building on established programs while maintaining Out-of-Door’s traditions will create opportunities for inspiring growth and development. As we move into the next phase of ODA’s educational and community impact, we look forward to a bright and impactful future filled with student-centered, engaging experiences inside and outside of the classroom.”