Principal, Upper School

Administrator / Full-Time

Milton Academy, Milton, MA

Reporting to the Head of School, the Principal oversees and leads all functions of the Upper School, including academics, student life, college counseling, residential life, athletics, student support, and faculty feedback and professional development. The Principal also serves as a key member of the school’s Leadership Team, collaborating with other members of Milton’s K–12 administration, including the principals of the other two divisions.

The Principal manages a large, complex, diverse Upper School of 700 students and 150 faculty and staff. The Principal builds on the strength of Milton’s history of developing insightful, independent learners, in support of the school’s mission to develop “creative and critical thinkers, unafraid to express their ideas, prepared to seek meaningful lifetime success.” A proven educator with significant classroom experience, the Principal must have excellent management, delegation, communication, and interpersonal skills. While always staying true to and advancing the school’s philosophy and values, the Principal must be open to receiving and incorporating feedback and insights from a variety of different constituencies. 

In addition, the Principal must model a commitment to individual growth and creativity among a diverse group of students, faculty, and staff. The Upper School Principal ensures that both new and existing policies, procedures, and programs uphold the school’s mission in its daily practices. The Principal must be able to inspire the faculty, foster a cooperative community spirit, and balance Milton’s tradition of excellence with an evolving, forward-facing vision.  

Milton’s Upper School has many strengths—among them, a long history of academic excellence; outstanding faculty and staff; eager, passionate, and engaged students; dedicated families; an impressive facility; and a strong base of support from which to build its future.

At the same time, the Upper School has high aspirations that present unique challenges and opportunities given its distinctive structure. The new Principal should be prepared to work with the Head of School, administration, faculty, and Board to:

  • Create a cohesive culture, rooted in shared values of excellence and respect;
  • Foster community and ensure that the values of diversity, equity, inclusion, and justice are integral to all aspects of the division;
  • Build and maintain trust among all stakeholders and bring clarity and transparency in decision-making;
  • Cultivate an Upper School administration that is collaborative and responsive to students, faculty, staff, and families;
  • Model and create systems for consistent, timely, and effective communication with all constituencies;
  • Enable feedback and accountability systems that foster faculty and administrative excellence and personal and professional growth; 
  • Ensure a best-in-class residential life program; and
  • Balance what are sometimes competing interests between the boarding and day aspects of the Upper School.

Please note that the Upper School Principal is expected to live on campus and fulfill residential duties.

Applications will be reviewed on a rolling basis, with the first batch starting on February 29.

Start Date:
The expected start date is July 1, 2024.

Click here for the full job description and to apply.

Milton Academy

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