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Head of School Search 2021

After an extensive nationwide search, The Out-of-Door Academy’s Board of Trustees has announced the appointment of Mrs. Debra Otey as the next Head of School, effective July 1, 2022.

Mrs. Otey was selected from a pool of impressive candidates after a thorough search process. This appointment is fully supported by the Head of School Advisory and Search Committees. The committees found Mrs. Otey to be a dynamic, accomplished, passionate educator, well-poised to lead Out-of-Door into its next chapter. 
Chair of The Out-of-Door Academy’s Board of Trustees Mr. Tom Murphy 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,” Mr. 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.”
Mrs. 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.
Mrs. Otey will lead the prestigious school starting in the 2022-23 school year. “I am excited to join a Pre-K–12 community that emphasizes character education and student wellbeing,” she explains. “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.”
The Board of Trustees is dedicated to continuing to expand the school’s college preparatory program with Mrs. Otey at the helm. The School’s curricular, programmatic, and physical expansion has set a precedent for academic, artistic, and athletic excellence, establishing The Out-of-Door Academy as one of the top independent schools in Florida.

2021 Head of School Search

The Board of Trustees’ most critical work at an independent school is identifying, recruiting, hiring, and supporting a mission-aligned Head of School. During Out-of-Door’s leadership transition, the Board committed to finding the right person to lead The Out-of-Door Academy in its next chapter. This leadership transition represents an opportunity for the School community to reaffirm its institutional values, as well as its mission and vision. The next Head will be an individual of outstanding character, whose personal and professional skills match the School’s culture and who will inspire and enable ODA to achieve its vision for the future. 

List of 3 items.

  • Search Process

    The Board engaged Educators Collaborative, Inc., a leading executive search firm, to conduct a comprehensive search. Please click here to learn more about Educators’ expertise in the field of not-for-profit education. The consultants who led our search process are listed below. 
    Doug CummingsJoan BeauregardSally Mixsell

    Following the April 1 announcement, the Board engaged in productive conversations with seasoned candidates for the interim position. On June 8, Mr. James Connor was announced as ODA’s Interim Head of School, effective July 1, 2021. We are excited to welcome this passionate educator to The Out-of-Door Academy. Mr. Connor served for 26 years as Head of School at Germantown Academy and recently served as Interim Head of School at Miami Country Day School. Mr. Connor has received many accolades for his leadership roles in academia throughout his career, including a commendation for service from the Board of Trustees at Germantown Academy. He will uphold the duties of Head of School until July 1, 2022.
  • Search & Advisory Committees

    The Board of Trustees created a Head of School Search Committee to take part in a thoughtful and thorough process to develop and assess prospective candidates. The goal of the Committee was to recommend one person to the Board for consideration as Out-of-Door’s next Head of School. The Search Committee was led by Board Chair Mr. Tom Murphy and consisted of members of the School's Board of Trustees: Sean Abrams, Deb Beck, Jamie Becker, Rob Crisci, Leigh Dalton, Ariane Dart, Teena Humphrey, David White, and Michael Wilson.

    The Advisory Committee, co-chaired by Dr. Kelly Rose and Mr. Ken Sommers, included parents and faculty representing all three divisions, as well as members of the school’s leadership, staff, and alumni groups. We thank the following individuals for their participation in this capacity: Fernando Azcona, Monica Baldwin, Charles Balliette ‘00, Tony Bonacuse, Doug Bradbury, Angel Cappar, Kerri Dowdell, Mietra Harandi, Mitzie Henson, Neil Hunn, Tammy Karp, Jordan Letschert ‘00, Katie Rauch, Kymberli Rivers, Terri Vitale, and Betsy Wild ‘01.

    We are incredibly grateful for the time, energy and thoughtfulness that we know these community members are employing in this process.
  • ODA Community Involvement

    The search for Out-of-Door’s next Head of School was an inclusive and multi-phase undertaking that allowed us to build a collective vision for the School’s next phase.

    Below you will find a list of outreach initiatives:
    • Community-wide survey:  A comprehensive survey was sent to the Out-of-Door community on May 2, 2021 with the goal of collecting feedback from all stakeholders.  This was a confidential survey with Educators Collaborative collecting submissions.
    • Discovery sessions: Consultants from Educators Collaborative conducted meetings with the Board and the faculty. The consultants have used information collected during those sessions to inform the type of leader who should guide us in the coming years.
    • Feedback:  Educators Collaborative accepted community member feedback and questions throughout the process.
    • Dedicated Webpage: This webpage was regularly updated with pertinent information.

The Out-of-Door Academy

LOWER SCHOOL |  Historic Siesta Key Campus  |  Pre-K – Grade 5
444 Reid Street, Sarasota, FL 34242  |  941-349-3223  |  Fax: 941-349-8133

  |  Uihlein Campus in Lakewood Ranch  |  Grades 6 – 8 |  Grades 9 – 12
5950 Deer Drive, Sarasota, FL 34240  |  941-349-3223  |  Fax: 941-907-1251
The Out-of-Door Academy does not discriminate on the basis of race, creed, physical ability, religion, sex, age, gender, sexual orientation, or national origin.
The Out-of-Door Academy is an equal opportunity employer.

© 2021 The Out-of-Door Academy