Upper School Head

Administrator / Full-Time

The Winsor School, Boston, MA

Upper School Head

The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Our diverse, vibrant community values intellectual curiosity, authentic engagement, and personal integrity and prepares young women to pursue their aspirations and contribute to the world. Winsor strives to create an environment of respect and inclusion.

Winsor’s unique location in the city of Boston fosters an intellectual culture that mirrors the dynamic energy, climate and innovative spirit of the city. Winsor enrolls approximately 475 students from more than 50 different local communities in and around Boston. Winsor’s reputation for academic excellence and success belies a warm and caring environment that encourages personal growth and lifelong friendships. Winsor seeks an experienced school leader who will embrace Winsor’s mission and further the strategic goals of the school as Head of Upper School, beginning July 1, 2022.

As a dynamic and responsive community, Winsor continuously evaluates and seeks to strengthen its diversity, equity, and inclusion work. Winsor has long strived to create an environment of respect and inclusion, to honor the dignity and humanity of every individual, and to teach those values and honor the principles of equity and inclusion. Now is a time of deep reflection for Winsor’s leadership, faculty, and community members.

Winsor honors each community member’s ethnicity, race, religion, gender identity, sexual orientation, socio-economic status, age, and physical and mental ability. The school is committed to providing a safe, supportive setting so that students have the opportunity to explore and to clarify their own beliefs and values, to take risks, and to think and speak for themselves. Winsor recognizes the importance of communication and of encouraging dialogue among all constituencies. Winsor will continue to encourage and support students, faculty, and staff to engage in all ways ranging from affinity and community building groups, a newly formed student board for equity and inclusion and professional development to engage on a personal or larger scale. Learn more about diversity, equity, and inclusion at Winsor.

Major Functions and Responsibilities:

The role and responsibilities of the Head of Upper School are central to the school’s leadership and crucial to the school’s daily administration.

The Upper School Head:

  • Oversees the academic, social and emotional well-being of Upper School students in coordination with the class deans, department heads, teaching and learning coordinator, school nurse, school counselor, and other key administrators
  • Is responsible for the day-to-day operations of the Upper School, which includes approximately 250 students and a talented faculty and staff
  • Collaborates with the associate head, academic administration, and department heads on curriculum and instruction
  • Communicates and meets with parents regarding issues of mutual concern, and holds regular Town Hall meetings with families
  • Works with the Lower School Head to provide a sense of community and common purpose for the entire school and to facilitate transition between the divisions
  • Works with the associate head of school and Lower School head to support department heads in all matters, including staffing, scheduling, and teacher supervision and development
  • Collaborates with the associate head and department heads to recruit, hire, evaluate, and retain Upper School faculty
  • Is a presence in the life of the school, including attending games, performances, student presentations, and regularly interacting casually with students, faculty and families in daily life
  • Leads Upper School division meetings for faculty and advisors
  • Supervises, guides, and supports the class deans
  • Runs Upper School meeting, supports and works with club leaders and student government
  • Partners with the School’s advancement department to coordinate communications between the School and parents/guardians
  • Speaks publicly, when called upon, about the Upper School curriculum and programs to audiences of families, alumnae, prospective students, and current students
  • Together with the registrar, manages the reporting of student progress
  • Has primary responsibility for Upper School student discipline, including the Honor

Review Board

  • Supervises the school counselor, the registrar, and teaching and learning coordinator
  • Reports to the head of school

Other roles:

  • Sits on the Academic Administrative and Department Heads committees
  • Is a member of the Administrative Council (senior administration of the school)
  • Sits on Admission Committee and assists in admission decisions for the Upper School
  • Typically teaches one class
  • Advises a group of 6-8 students
  • Serves on or leads committees as warranted


  • At least 5 years of administrative and teaching experience in secondary education
  • Demonstrated success working with a variety of constituents in the areas of diversity, equity, and inclusion
  • Experience working with students in an all-girls environment, or a keen interest and understanding of the benefits and importance of an all-girls education.
  • Masters degree or PhD preferred


  • Strong organizational skills and the ability to handle multiple tasks simultaneously
  • A confident professional who is collaborative, flexible, inclusive, and forward thinking
  • Ability to form relationships, manage conflict, and build consensus
  • Exceptional leadership and communication skills
  • Understanding of and appreciation for the whole student experience, including, but not limited to extracurricular opportunities, advising, athletics, the arts
  • An understanding of the tensions that arise in a high-performing school, and the central role student wellness plays in education
  • A desire to work in fast-paced but warm, collegial environment

Nothing in this job description restricts Winsor’s right to assign or reassign duties and responsibilities at any time. The position is at will, which means that it can be terminated by the employee holding the position or by the School at any time, with or without notice or cause.

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The Winsor School

Boston, MA
Elementary, Middle School, High School