Reports to: Director of the Middle and Upper School
Location: Andrews Osborne Academy – Willoughby, Ohio
Position Overview:
Andrews Osborne Academy seeks a relational, highly organized, and mission-aligned educational leader to serve as the Assistant Director of the Middle and Upper School (Grades 6–12). This is a key leadership role designed to support the growth and experience of all students and faculty. The Assistant Director will help guide day-to-day operations, academic support, student life, and community engagement.
The successful candidate will be proactive, flexible, and deeply committed to nurturing students academically, socially, and emotionally. They will be a consistent presence in the halls, classrooms, and at school events, serving as a trusted figure for students, faculty, and families alike.
Key Responsibilities (including but not limited to):
Leadership & School Culture
Serve as a visible, daily presence in both the Middle and Upper School. Supporting faculty, students, and parents while reinforcing school values and behavioral expectations.
Clearly articulate school policies, expectations, and procedures across grades 6–12; ensure consistent communication with all constituencies.
Assist in maintaining an orderly, and safe learning environment that reflects an understanding of the educational, developmental, and social-emotional needs of students.
Collaborate with the Director of Middle and Upper School and Head of School to set the tone and direction for 6–12 programming and culture.
Academic Program & Faculty Support
Observe, evaluate, and support instructional and non-instructional staff; help onboard and mentor new faculty and lead professional growth initiatives.
Review and approve academic comments and reports quarterly; oversee grading and reporting systems to ensure clarity and consistency.
Track academic progress and oversee support processes including academic watch and probation.
Assist with curriculum coordination and faculty meetings; attend department meetings.
Collaborate on the construction and management of the 6–12 academic schedule; help assign students and teachers to appropriate classes.
Assist in academic guidance to students, including scheduling adjustments and intervention planning.
Student Life & Engagement
Manage student behavior and discipline in grades 6–12, including attendance, tardiness, and absences.
Guide grade-level advisory programs; support Lead Advisors in the implementation of developmentally appropriate advisory curriculum.
Support student organizations, activities, and clubs; coordinate “Phoenix Time” and other enrichment or elective periods.
Serve as an administrator on duty; maintain visibility at athletic, academic, and co-curricular events throughout the year.
Events & Ceremonies
Organize and help execute major student-centered events such as student assemblies, academic ceremonies, field days, Spirit Weeks, and other community-building activities.
Support the planning of school-wide milestones such as Middle School and Upper School awards, moving-up ceremonies, and commencement.
Maintain and contribute to the 6–12 calendar of events.
Operations & Communications
Collaborate closely with the Admissions team on student retention, onboarding, and recruitment initiatives; assist in interviews and evaluations of prospective students.
Participate in faculty hiring and evaluation processes.
Communicate clearly and consistently with families; support the development of newsletters, school publications (e.g., Phoenix Press), and other outward-facing materials.
Assist in preparing and managing budgets; work with Advancement to seek additional funding opportunities when possible.
Institutional Responsibilities
Attend leadership, director, department chair, and Health & Wellness meetings.
Represent the 6–12 program in conversations with the Head of School and other administrative leaders.
Attend professional development workshops and conferences as appropriate.
Fulfill additional responsibilities assigned by the Director of Middle and Upper School or Head of School.
Qualifications and Skills:
Bachelor’s degree required; Master’s degree in Educational Leadership, Curriculum and Instruction, or a related field preferred.
Minimum of 3–5 years of experience in teaching or educational leadership, ideally within a 6–12 or middle/upper school setting.
Strong interpersonal, organizational, and communication skills with students, colleagues, and parents.
Proficiency in Google Suite required; familiarity with Blackbaud a plus.
A deep understanding of the developmental needs of middle and upper school students.
A collaborative spirit and commitment to supporting a diverse school community.
Proven ability to manage multiple priorities and lead with clarity, compassion, and professionalism.
Why Andrews Osborne Academy?
Andrews Osborne Academy (AOA) is a co-ed, day and boarding college preparatory school located on a beautiful campus in Willoughby, Ohio just outside Cleveland. With students from 30 countries and 15 states, AOA offers a diverse, and academically rigorous environment. Our supportive faculty and staff work to ensure each student is known, challenged, and celebrated.
Andrews Osborne Academy
38588 Mentor Avenue
Willoughby, OH 44094
440.942.3600
All applicants should know that a formal BCI/FBI background check will be a part of this hiring process.