Assistant Director of Upper School
Job Details
Oak Hall School - Gainesville, FL
Full-Time, 12 month
4 Year Degree
Position Purpose & Key Responsibilities


Throughout their academic journey, Oak Hall students learn to think critically, communicate purposefully, collaborate effectively, and lead confidently. To guide students through this journey, and to help prepare students to pursue matriculation at a wide range of competitive colleges around the country, Oak Hall School seeks a dynamic, experienced, and collaborative educational leader to join our Upper School team as Assistant Director of the Upper School.  The ideal candidate is a flexible creative thinker, thrives when managing multiple initiatives, and is passionate about student-centered education. We invite well-qualified applicants to apply for this position which will begin in July, 2023.

  • Actively support the mission of the school in all aspects of student, faculty, and family engagement
  • Assist the Director of Upper School and administrative staff in overseeing the daily operations of the division
  • Assist the Director of Upper School to cultivate and model an atmosphere of respect and inclusivity with an understanding of the individual differences, strengths, and challenges of students, faculty, and staff
  • Mentor and support the development of Upper School teachers and identify professional development opportunities geared toward teachers’ growth in all areas
  • Take a lead role in the planning and execution of special events, ceremonies, parent informational sessions, as assigned
  • Communicate with parents to facilitate comprehension of the School’s program
  • Assist with and/or lead divisional meetings
  • Participate in the faculty evaluation process
  • Collaborate with the Director of Enrollment Management and Director of Upper School to admit mission appropriate new students into the Upper School
  • Collaborate with the Director of Upper School and other administrators in the hiring and retention of Upper School faculty
  • Collaborate with the Director of Upper School to manage the student, faculty, and daily class schedule
  • Develop and deliver up to two class sections, as assigned and in accordance with the expectation of all classroom teachers
  • Promote a learning environment that ensures high levels of learning for all students
  • Instill, promote, and model a mindset of life-long learning
  • Partner with existing faculty in leadership of clubs and extracurricular activities
  • Work collaboratively with the Upper School team, and the greater Oak Hall community
  • Serve as Advisor to a group of assigned students; mentor and advocate for your students
  • Maintain expertise in subject matter through professional development
  • Be a role model of integrity and professionalism
  • Meet regular and predictable attendance requirements, including attending division and other school meetings, professional days, graduation, Late Start meetings, sporting events, evening and weekend special events, and other required events
  • Adhere to School policies as described in the Employee Handbook and other materials
  • Other duties as assigned




  • Bachelor’s degree required; Master’s degree preferred
  • A minimum of five years of teaching experience, preferably in an Upper School or higher education
  • Strong background in school leadership responsibilities and/or mentoring required, preferably in an independent school setting,
  • Demonstrated administrative, facilitative, and presentation skills
  • Empathetic, open-minded listener
  • Demonstrated planning, organizational, and time-management skills to effectively prioritize multiple initiatives simultaneously and achieve desired goals and successful outcomes within defined periods of time
  • Must possess a keen understanding of the development and social-emotional needs of upper school students
  • Must possess a strong commitment to a balance between academics and co- and extra-curricular activities
  • Must be friendly and approachable, and possess the people skills and leadership style to effectively inspire, manage, collaborate with, and mentor a team as a respected member of the school community
  • Comfortable and confident leading difficult conversations with students, parents, and/or faculty
  • Must understand and possess the finesse required to lead with a flexible, yet decisive style
  • Excellent interpersonal, written, and oral communication skills with a demonstrated ability, willingness, and judgment to communicate effectively and form positive relationships with students, parents, colleagues, and other constituencies in an independent school setting
  • An extraordinary work ethic and the ability to accept and meet unexpected challenges with grace and a positive attitude
  • Knowledge and understanding of various learning styles and differentiated instruction
  • Ability to inspire, engage, empower, and educate and evaluate students with vigor and creativity
  • A history of commitment to professional development and life-long learning
  • A high degree of professionalism, collegiality, and personal conduct both in and outside of school
  • Enthusiasm and commitment to the vision and Mission of the School

Physical Requirements and Work Environment:

  • Works in an environment dealing with a wide variety of challenges, deadlines, and a varied and diverse array of contacts
  • Regularly uses close and distance vision
  • May stand for extended periods of time
  • Ability to work long hours
  • May work at a desk and computer screen for extended periods of time
  • Ability to visually and audibly locate students under their supervision
  • Occasionally turn, bend, reach, stoop, and squat
  • Ability to actively circulate throughout the diverse campus environment
  • Works primarily in a traditional climate-controlled classroom environment
  • Work intermittently in outside weather conditions, including extreme heat and cold.
  • Ability to occasionally lift, push or pull up to 20 lbs


Oak Hall is proud to offer a comprehensive employee compensation package, including a competitive salary, health and wellness benefits, and generous retirement plan options to benefits- eligible employees. Qualified candidates should be prepared to upload a cover letter, resume, and copies of transcripts.


Oak Hall School is committed to the principle of equal opportunity in employment.  It is Oak Hall’s policy to provide equal employment opportunities and administer terms and conditions of employment without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, age, disability, pregnancy, genetic information, marital status, or other legally-protected characteristic in accordance with applicable federal, state, and local laws.