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Principal, Upper School

Department: 01-51110-501 Us Principal Exempt

Position: Principal

Department: Upper School; Head of School’s Leadership Team

Location: Warren Hall, Milton Academy Campus, Milton, Massachusetts

Hours: Full-time with the flexibility to work nights and weekends

FLSA: Exempt

Classification: Staff (12 months)

Milton Academy is an independent college preparatory K–12 school, boarding and day in grades 9–12, located just outside of Boston.

Milton Academy cultivates in our students a passion for learning and a respect for others. Milton students grow by developing their own identities, learning from and listening to the lived experiences of others, and living and working among peers whose differences they accept with respect and care.

In our ongoing work to create an environment that confronts bias, injustice, and bigotry, we encourage each other to be open to learning, explore our histories and identities, and seek to understand the world around us with a critical lens. At Milton, we prepare students to partner with their future communities to create a more just world, and to have the courage to speak up and live by our motto, “Dare to be true.”

Summary of Position:

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.

Key Responsibilities:

  • Leadership: The Principal will provide critical leadership to all stakeholders; embrace the complexity, challenges and opportunities of the Upper School, and provide strategic direction, setting priorities that reflect the school’s values, ambitions, and resources.

    • Serve as a key member of the K–12 Leadership Team, collaborating with senior administrators to lead and manage the school.

    • Actively engage in institution-wide planning.

    • Use data-driven decision making to ensure best-in-class programs and standards.

    • Set high expectations for Upper School employees.

    • Lead, empower, and delegate to Upper School administrators and managers, ensuring consistent, forward progress.

    • Continue to cultivate and strengthen residential and co-curricular programs—including athletics, the arts, speech, and robotics, among others—to ensure that they align with the school’s learning environment.

    • Ensure that changes are driven by collaborative decision-making and inclusive implementation processes.

    • Ensure a healthy and safe environment for all community members through effective risk management.

      • Emphasize health and wellness best practices.

      • Provide appropriate training and support for faculty, staff, and students.

      • Play a key role in ensuring student and employee-related incidents are thoroughly reviewed, ensuring that policies and processes are followed.

    • Manage the Upper School budget, stewarding the school’s resources wisely, aligning the Upper School’s resources with its strategic objectives and in support of student programs.

  • Culture and Values: Cultivate a culture consistent with Milton’s mission and values.

    • Passionately support academic excellence and continue to inspire a culture of innovation.

    • Continually and consistently communicate Milton’s culture and values to all constituents.

    • Provide guidance and support to achieve appropriate resolution when situations occur that are inconsistent with Milton’s culture and values.

    • Work with the Faculty Council to understand and address concerns and questions brought forward by the faculty.

  • Management and Operational Oversight: Oversee and direct all Upper School functions, including but not limited to academics, employee supervision, professional development, diversity initiatives, student life and support, the boarding program, college counseling, and athletics—creating an environment where people feel inspired, motivated, empowered, and supported.

    • Ensure that an appropriate administrative structure exists within this complex division.

    • Engage with faculty and staff in critical discussions of pedagogy and curriculum; technology; and co-curricular and residential programming.

    • Oversee workload distribution, including class offerings and sizes, co-curricular activities and residential life support.

    • Oversee the residential life program, including decisions related to student and adult housing.

    • Oversee/manage Upper School people and talent, collaboration with the Human Resources department, including:

      • Build upon and strengthen our Upper School talent management strategy.

      • Continue to recruit, retain, and develop a strong Upper School administrative team.

      • Ambitiously recruit, develop, retain, and support excellent educators.

      • Oversee hiring for all Upper School positions in accordance with best practices while being highly responsive to Milton’s needs in every area.

      • Ensure strong onboarding, mentorship, and professional development programs are in place.

      • Focus on professional development and ongoing improvement for faculty and staff, prioritizing accountability and feedback.

      • Oversee the Upper School faculty performance evaluation process, ensuring evaluations are completed in a timely way and in accordance with policy.

      • Ensure proper documentation and distribution of all necessary institutional and division policies and procedures—both those that are legally required and those outlined within Milton’s faculty handbook and personnel policies.

      • Manage the Upper School faculty sabbatical program.

    • Ensure that the annual calendar reflects Upper School priorities and plans.

  • Communication: Maintain clear, effective communication across all school constituencies.

    • Demonstrate exceptional verbal and written communication skills.

    • Communicate in a voice that is thoughtful, inspiring, and authentic.

    • Listen empathically.

    • Communicate effectively and consistently with a wide variety of school constituencies, including students, faculty, families, staff, and administrators across multiple channels including in writing, conversation, public speaking, and various digital channels.

    • Regularly speak in front of large audiences, managing dynamic conversations and adeptly responding to real-time questions.

  • Diversity, Equity, Inclusion and Justice:

    • Continue to build support and drive measurable progress on access, equity, and belonging among all community members, supporting Milton’s aspirations to serve as a model for other institutions.

    • Collaborate regularly and conscientiously to ensure that decision making considers these values.

    • Communicate positive outcomes, issues, and support continuous improvement.

    • Collaborate among all community members.

  • Community Engagement:

    • Appropriately represent Milton in key Upper School moments, serving as an inspiring and compelling spokesperson for the Upper School and engaging students, families, students, alumni, and donors.

    • Forge personal connections with and demonstrate positive leadership to all Upper School students, faculty and staff.

  • Other duties as assigned

Other Professional Expectations and Responsibilities:

  • Work cooperatively with students, families, peers, administration, and community members.

    • Teach at least one course section each semester.

    • Serve as an advisor to a group of up to nine students, engaging them in weekly meetings and fulfilling all advisory responsibilities.

  • Serve as an administrator on duty for the residential program, facilitating residential programming when on duty.

  • Demonstrate a commitment to the success of each student, especially in the areas of social and emotional development.

  • Support colleagues and act with respect and generosity toward others, assuming the competence and good intentions of all members of the community.

  • Exhibit skills in collaborative problem-solving, critical thinking, and teamwork.

  • Meet deadlines.

  • Abide by school policies and procedures as outlined in the provided handbooks.

  • Communicate with the Head of School and other key constituencies when unable to meet any professional obligation.

Desired personal qualities:

  • A forward-leaning, intellectually curious educator who finds great joy in the daily life of the school.

  • A broadly engaged individual, who is courageous, open, and enthusiastic.

  • A leader with good judgment and a strong internal compass.

  • Patient and graceful under pressure, with the ability to anticipate future needs and potential impacts.

  • Confident, willing to listen empathically, make decisions, and share credit.

  • A sense of humor.

Supervision to be received: Supervised by the Head of School.

Supervision to be exercised: Dean of Faculty, Academic Dean, Dean of Students, Dean of Teaching and Learning, Director of Equity and Inclusion, Athletic Director, Director of College Counseling, Assistant to the Upper School Principal; Department Heads; general oversight of all faculty in grades 9–12 with daily oversight provided by department heads.


Required: A bachelor’s degree

Preferred: A master’s degree



  • At least 10 years of progressive leadership experience in secondary schools

  • Demonstrated effectiveness in providing a high-quality student learning environment

  • Demonstrated effectiveness in providing a positive faculty work culture

  • Deep experience with providing professional feedback and development for faculty

  • Successful track record of change management, including the demonstrated ability to consider all sides of an issue, make decisions, and navigate implementation

  • Demonstrated ability to delegate to and manage a large, diverse team

  • Demonstrated ability to prioritize among multiple initiatives and projects


  • Boarding school experience

  • Experience leading within a complex organization

  • Deep experience with transformational DEIJ work in schools

  • Familiarity with restorative justice practices

  • Oversight of multi-million dollar budgets



  • Proven consensus-building skills.

  • Ability to lead, manage, motivate and inspire groups and individuals across the organization.

  • Ability to communicate difficult concepts and nuanced issues, both verbally and in writing.

  • Demonstrated technological expertise.

  • Ability to work collaboratively with internal and external constituencies.

  • Understanding of confidentiality and related issues.

  • Receptiveness to supervision and professional development.

  • Desire to be a part of a dynamic educational community.

Physical Abilities:


  • Must be able to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.

  • Must be able to move around the Milton Academy campus without restriction.

  • Must be able to lift up to 10 pounds.

The essential functions and basic skills have been included in this job description; it is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

An equal opportunity employer, Milton embraces diversity and the pursuit of excellence. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race (including natural and protective hairstyle), color, sex (including pregnancy and pregnancy-related condition), sexual orientation, gender identity, gender expression, religion, religious creed, physical or mental disability, age, genetic information, veteran status, ancestry, citizenship, national or ethnic origin or any other status protected by applicable law.

More Information About Milton Academy


Milton Academy seeks a motivated and strategic leader to serve as its new Upper School Principal for July of 2024.

Founded in 1798, Milton Academy’s Upper School is a highly selective, coeducational, grades 9–12 boarding and day school on a 125-acre campus, located in a beautiful, vibrant suburb immediately adjacent to Boston. It is a diverse and lively school, enrolling 700 students from 26 states and 31 countries. Nearly 50 percent of students board on campus; both boarders and day students enjoy a caring, welcoming and dynamic campus life. Young people and adults at Milton value the diversity of the school community and its unique balance of international and national connections, cosmopolitan energy, and wonderful facilities, location, and resources as crucial elements of living and learning in this exceptional environment. With more than 1,000 students, 450 full- and part-time faculty and staff across its K–12 operations, an operating budget of approximately $90 million, and an endowment of approximately $400 million, the scale of Milton’s enterprise is comparable to many liberal arts colleges.

Milton focuses on nurturing every student’s individual voice and their commitment to community—preparing them to be positive and passionate contributors in our rapidly changing world. It is a place of open and unlimited intellectual growth and discovery, where students feel supported in being themselves.

Debate and alternative points of view are encouraged, academic excellence is celebrated, and immersive issues regarding diversity, equity, inclusion and social justice are core to the school’s identity.

At the heart of the school is the primacy of the relationship between the teacher and the student. In this intellectually alive community, students are mentored, motivated, and challenged as they find their voices, passions, and creative aspirations. Individuality is encouraged—even prized—but embraced through the lens of belonging and contributing to this unique community. The Upper School Principal is charged with carrying forward the most essential elements of this powerful school culture and experience while inspiring and guiding the school toward a more unified, aspirational, sustainable, and administratively effective future.

Mission and Motto

Milton Academy’s motto resounds in the minds and hearts of today’s students and graduates. Often cited by both faculty and students as the litmus test for word or action, “Dare to be true” not only states a core value, it describes Milton’s culture.

Grounded in values, deeply respectful of diversity, and thoroughly aware of the issues of their time, Milton students graduate fully prepared to meet their own high expectations wherever their lives take them.

The school mission provides purpose across our K–12 community: “Milton Academy cultivates in its students passion for learning and a respect for others. Embracing diversity, equity, inclusion, justice, and the pursuit of excellence, we create a community in which individuals develop competence, confidence and character. Our active learning environment, in and out of the classroom, develops creative and critical thinkers, unafraid to express their ideas, prepared to seek meaningful lifetime success and to live by our motto, ‘Dare to be true.’”

Curriculum and Program

Milton Academy offers a wide array of exciting courses shaped by a disciplined path to subject mastery and earning a diploma. Pedagogical and curricular innovations are hallmarks of our teaching approaches across all academic departments. Small, energetic classes and Harkness table-style teaching fundamentally distinguish Milton’s learning culture. Students see their teachers as intellectual mentors and treasure their connections with faculty long after graduation.

Opportunities in the arts, athletics, service, activities, and clubs and student-run organizations are wide-ranging and vibrant, supporting almost every student interest and ambition. Students with special interests and elite skills are supported in deepening their expertise, while the school also provides plenty of chances for them to discover and enjoy new activities and passions. One of the great strengths of the boarding/day mix at Milton is that everyone benefits from a dynamic campus life, with students from near and far all sharing their interests, talents, and ideas with each other during traditional school hours, evenings, and weekends.

Diversity, Equity, Inclusion and Justice

Believing that diversity, equity, inclusion, and justice are essential to delivering on its mission, Milton Academy’s commitment to these values is strong and longstanding. Fostering respect, responsibility, and empathy at school and in the wider world, Milton’s commits to give voice and respect to people representing a breadth of race, ethnicity, gender, sexual orientation, family structure, physical ability, and religious and political affiliation. Our community welcomes those who keep their minds and hearts open to difference.

Milton’s diversity is fundamental to its excellence. Students of color make up 52 percent of the Upper School student body. Throughout a student’s time in the Upper School, they have many opportunities to explore and understand their own identities and those of their classmates. More than 20 cultural clubs and affinity groups exist as spaces for dialogue, identity development, support, and empowerment. Milton has adopted and continues to implement a comprehensive diversity, equity, and inclusion strategic plan to position the school at the forefront of equity and justice. Restorative justice practice, a school-wide approach to ensure accountability to community standards, is an important piece of Milton’s DEIJ approach. It will be critical for the new Upper School Principal to be experienced and eager to engage in this work at Milton.


In classrooms and labs, stages and playing fields, as teammates and as leaders, Milton students stand out because of their desire to grow, achieve and make a difference. The community values empathy, courage and connection as students and adults engage with one another and in the world beyond campus. This year alone, Milton has seen Upper School students shine on our stages; achieve athletic greatness on the New England and national levels; testify before state lawmakers to advocate for important legislation; develop apps, start their own businesses, participate in cutting-edge AI research; rocket to the top rankings in robotics and math competitions; and give back to many communities in meaningful ways. Graduates carry Milton’s spirit of excellence with them becoming leaders and innovators in science, business, medicine, art, government, social justice, entertainment, academia and technology.

Learn more about Milton Academy Upper School students on the school website.

Faculty and Staff

Milton is more than a place to work, it’s a calling driven by a passion to make a difference in the lives of bright, aspiring students of all ages and to prepare them to be thoughtful, well rounded contributors to our world.

Every employee at Milton Academy is an educator—deeply talented, engaged, and dedicated to the development of the exceptional students in our care. Genuine connections between brilliant faculty members and highly capable and motivated students inspire great teaching and learning. Staff members are similarly gifted and devoted to the Milton community and its students. The next Upper School Principal will be charged with building upon ongoing efforts to deepen the awareness and appreciation between faculty and staff of each group’s important contributions to the school.

Learn more about Milton Academy Upper School faculty and staff on the school website.

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