Wakefield School
The Plains, VA
Grades PS - 12 with 320 students

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Reporting to the Head of School, the Head of Middle School must be an experienced, progressive educator with a deep understanding of middle school aged children to lead and inspire its Middle School community of teachers and students. This is a senior administrator position, working closely with the Head of School and other division heads and administrators to implement Wakefield’s strategic plan and educational  programs.
SUMMARY - The Head of Middle School will be a strategic partner and thought leader who will help strengthen and advance Wakefield’s vision and strategic plan for the Middle School. By working in close partnership with key constituencies, the Head of Middle School will prioritize the following:
  • Enhance our environment for students and faculty to thrive and grow; to rely on and trust in one another.
  • Understand and clearly explain the relationship between traditional and progressive education, and what it looks like in Middle   School.
  • Examine and improve transitions from Lower School to Middle School and Middle School to Upper School in partnership with other division heads and the Head of School.
  • Moving forward with bold and innovative ideas while respecting and honoring important and deeply embedded Wakefield and Middle School  traditions.
  • Collaborates with faculty and staff to value and support the importance of middle school education
  • Oversees the development, alignment, and evaluation of curriculum in collaboration with the instructional leadership team of the school
  • Hires, in conjunction with the Head of School, faculty and coordinates faculty duties in and out of the classroom
  • Directs the professional learning and evaluation programs for all Middle School faculty and staff and specific cross-divisional  faculty
  • Maintains open communication with families through regular meetings, Wakefield Parent Association groups, and written information and presentations
  • Oversees the development of the Middle School schedule and allocation of learning, social, and play  spaces
  • Develops and maintains community expectations designed to reinforce positive and respectful student behavior
  • Supervises preparation, planning, and enrollment in student courses and programs
  • Prepares and controls divisional budget; participates in and contributes to all-school  budget  discussions  and decisions
  • Directs and supervises safety policies and practices for Middle School students, faculty, and staff
  • Works with the Director of Admission, faculty, and prospective families to ensure a mission-appropriate student body in the Middle  School
  • Partners with Division Heads and the Admission team to ensure effective student transitions, retention, and placement
  • Shares responsibility with other Division Heads for faculty evaluation, curriculum, and school programs, on and off campus, during and outside the school    day
  • Supervises or coordinates other educational or personnel matters delegated by the Head of  School
  • Actively supports the school through participation in the variety of activities that make Wakefield School a vibrant  community
  • Participates in ongoing professional learning and training to support Wakefield’s mission
  • Other duties as assigned by the Head of School
  • Enthusiasm and excitement to work with and get to know middle school  students
  • Ability to be an educational entrepreneur with regard to curriculum programs and approaches, keeping abreast of educational trends in  curriculum
  • Exceptional written and verbal communication skills
  • Change management skills
  • Supervision, evaluation, and coaching   skills
  • Organization and time management  skills
  • Technology  skills, including Microsoft and Google   Suite


  • Bachelor’s degree required; Master’s degree   preferred
  • At least seven years of experience in a school environment, independent school experience preferred
  • At least two years of supervisory/management  experience
  • Knowledge of progressive education and experience as a teacher and administrator in grades 6-8 is desirable
  • Experience in navigating challenging conversations about sensitive issues

Already an active candidate? Contact your counselor!

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