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Head of Middle School

Westchester Country Day School
High Point, NC Full Time
POSTED ON 2/21/2026
AVAILABLE BEFORE 4/21/2026

Westchester Country Day School, a PreK-12 college preparatory school located in High Point, NC, seeks a Head of Middle School to start on or near July 1, 2026. Candidates must possess a minimum of a master's degree in Education, Educational Leadership, or related field. In addition, candidates must have the following:

  • Ability to foster a positive and inclusive school culture that supports the academic, social, and emotional well-being of students.
  • Excellent communication, interpersonal, and leadership skills.
  • Ability to collaborate effectively with diverse stakeholders, including students, parents, faculty, and staff.
  • Commitment to promoting belonging within the school community.

Specific job responsibilities include:

  • Act as the educational leader of the school division, responsible for its day-to-day operation.
  • Direct the activities of the members of the division staff in the performance of their duties. 
  • Function as the chief articulator of that division’s programs, expectations, behavioral guidelines, and other information necessary to ensure that all constituencies are fully informed, consistent with their individual roles. 
  • Observe, supervise, and help evaluate the faculty in the development and implementation of curriculum; supervise the teaching process, and to review and evaluate the academic programs. 
  • Maintain a visible presence in all areas of the school; work toward a resolution of all problems, both routine and unique, as they arise; and keep the Head of School informed of the general programs, activities, and problems of the division.
  • Work with the Head of School and Chief Financial Officer to create and manage divisional budgets/purchases in conjunction with the department heads.
  • Maintain congruence between the school’s board-approved mission statement and all activities of that division. 
  • Lead in the articulation of the school mission, school goals, department goals, course objectives, materials, methods and means of assessment. 
  • Provide an orderly, controlled environment in which learning can take place and a school climate that is supportive and reflects high morale. 
  • Assist in the admission process for the testing, interviewing, and evaluating of applicants for enrollment. 
  • Perform other duties as assigned by the Head of School. 

Interested candidates can learn more about working at WCDS and apply for this position by visiting the school's Employment web page. Inquiries may be directed to Penny Rowe, penny.rowe@westchestercds.org.

Salary.com Estimation for Head of Middle School in High Point, NC
$90,826 to $118,326
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