Job Description

Reports to: Director of the Middle and Upper School
Location: Andrews Osborne Academy – Willoughby, Ohio

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.

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.

Resumes should be sent to Upper School Director, Chris Fox, at [email protected].

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.

Job Tags

Similar Jobs