Head of Upper School

Administrator / Full-Time

Fay School, Southborough, MA


The Head of Upper School (Grades 7-9) oversees the Upper School program, with a focus on student life, student conduct and discipline, and residential life. Central aspects of this role include: establishing expectations and sustaining a positive tone for Upper School students and faculty; overseeing the residential life program for boarding students; supervising and supporting faculty in meeting standards of excellence in teaching, advising, and communication with parents/guardians; and collaborating effectively with colleagues, including the Head of School, other senior administrators, and members of the faculty, and staff.

The Head of Upper School reports to the Head of School and is a member of the Head’s Administrative Team, which also includes the Primary School and Lower School division heads and other senior administrators.  The Dean of Residential Life, three Class Deans, and an administrative assistant report to the Head of Upper School. This position is full-time with benefits, including campus housing.

Responsibilities include:

  • Monitoring the academic, social, and emotional development of Upper School students
    • Fostering students’ academic, athletic, and artistic growth
    • Coordinating the reporting of grades and teacher/advisor comments, effort grades and ratings, and academic awards
    • Addressing concerns about students in collaboration with deans, advisors, teachers, counselors, learning specialists, administrators, and parents/guardians
    • Monitoring Upper School student attendance
  • Overseeing the Residential Life Program
    • Collaborating with the Dean of Residential Life to develop and maintain a structured and supportive boarding program that teaches life skills and develops self-reliance
    • Ensuring the safety and supervision of boarding students
    • Coordinating logistical support for international boarders and their parents/guardians
  • Overseeing the Upper School advisory program
    • Developing advisory curriculum and activities
    • Assigning, training, and supervising advisors
    • Communicating with parents/guardians regarding advisory program goals and activities
  • Overseeing Upper School student discipline
    • Establishing expectations and guidelines for student conduct
    • Maintaining student discipline according to school policies
    • Responding to concerns about student conduct
    • Investigating disciplinary matters, chairing Discipline Committee meetings, and consulting with the Head of School to determine disciplinary consequences
    • Communicating with Upper School faculty and students about disciplinary matters
  • Participating in the hiring, supervision, and evaluation of the Upper School faculty
    • Collaborating with the Director of the Educational Program and academic department chairs on faculty hiring and retention
    • Supervising the Dean of Residential Life and Class Deans
    • Conducting professional evaluations of Upper School faculty members
  • Leading Upper School faculty and student meetings
    • Running Upper School grade-level and full faculty meetings
    • Planning Upper School Morning Meetings
    • Collaborating with the Director of Equity and Inclusion to facilitate student multicultural and affinity groups
  • Managing communication with Upper School families
    • Communicating with individual parents/guardians as needed
    • Sending periodic communications to families about Upper School life
    • Leading grade-level Parent Coffees
  • Collaborating with other administrators to plan and implement special events
    • New student orientation
    • Upper School Back-to-School Night
    • Founders’ Weekend
    • Grandparents/Special Friends Day
    • Service learning activities and trips
    • Prize Day, Commencement, and other end-of-year events



The ideal candidate will have at least five years of middle school teaching experience and at least five years of administrative leadership experience in independent school settings. Experience in a boarding school environment is essential, and work with international students is beneficial. A master’s degree is strongly preferred. Fay School seeks candidates who will reflect and enhance the racial, ethnic, cultural, and gender diversity of our school community.

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Fay School

Southborough, MA
Elementary, Middle School, High School
Boarding, Day
All Gender