Exciting Update about Oakwood Middle School

Oakwood School has consistently been in high demand, and recent years have brought purposeful and remarkable growth to the school. Increasingly, families are recognizing and appreciating the value of a more intentional education rooted in Oakwood's educational philosophy of confident self-expression, high academic expectations, passionate expertise, strong moral examples, and unbridled exploration.

An exciting update is underway for one of the school’s four divisions, as intentional changes are being made to enhance the Middle School experience and expand opportunities for more students within the community to benefit from an Oakwood education. These updates, carefully planned over several years, include increasing the number of students per grade in Middle School from 48 to 60. This expansion will allow for smaller class sizes, the hiring of additional faculty, and enhanced elective offerings, all of which will support more personalized student learning and a more robust overall educational experience. While the transition to 60 students per grade in Middle School will occur incrementally, Oakwood is eager to lay a strong foundation for this growth and strengthen the Middle School experience.

As part of this Middle School expansion, Oakwood is proud to announce the appointment of Dr. Josh Watson as the inaugural Middle School Head & Principal. Following a thorough and competitive search process, including extensive interviews and on-campus visits, Dr. Watson was selected from a pool of highly qualified candidates from across the country and beyond. His appointment is the culmination of efforts to expand Oakwood's leadership structure, in response to the school’s ongoing enrollment growth, as initially announced last February.

Dr. Watson brings over 25 years of experience as an educator and school leader, including his start as a middle school teacher in Orlando, Florida, after graduating summa cum laude from the University of Northern Iowa with a B.A. in Humanities. He went on to teach Latin and English at the University of Denver High School while earning an M.A. in Classics from the University of Colorado. The majority of Dr. Watson’s career has been dedicated to independent schools in Hawaii, where he held several key leadership roles over two decades. These include serving as Head of School at La Pietra – Hawai‘i School for Girls, Assistant Principal for Student Life at Mid-Pacific Institute, and Assistant Head of School at the Academy of the Pacific, among others. Dr. Watson also holds an M.Ed. in Educational Leadership and an Ed.D. in Professional Educational Practice, both from the University of Hawai‘i.

Throughout the hiring process, including a full day on campus interacting with faculty, staff, students, and parents, Dr. Watson demonstrated the qualities and experience necessary to serve as a dedicated and mission-driven leader for Oakwood’s Middle School. His vision aligns seamlessly with the school’s innovative educational environment, fostering confident curiosity and unbridled exploration.

Dr. Watson’s arrival is enthusiastically welcomed, particularly by Mrs. Christine Shales, who has been a key member of Oakwood’s leadership team since 2015, serving as Lower School Head & Principal and, more recently, taking on the dual role of Middle School Head & Principal since 2022. The school extends its deepest gratitude to Mrs. Shales for her outstanding leadership and dedication over the past three years, during which the Middle School has continued to thrive. Mrs. Shales will continue in her current role through the remainder of the school year before focusing exclusively on the Lower School starting next year.

Dr. Watson will officially join Oakwood this spring as part of the transition process in preparation for the 2025 school year, and the school community looks forward to the new opportunities his leadership will bring.