Head of School Search

The Board of Trustees of Tremont School is beginning a search for the next Head of School. We are grateful for the outstanding efforts of Bill Wilmot, our founding Head of School, who is stepping down after six successful years to pursue other interests within the Tremont School community.

Tremont School is a pioneering and innovative school in both community and curriculum. Offering a personalized and student-driven approach to learning, Tremont School embraces diversity to create a distinctively supportive and collaborative community.

Currently with 45 students in grades 5-11, Tremont School will graduate its first class next year. Tremont School has aggressive goals for growth, taking advantage of our wonderful new facility in Lexington, MA on the campus of Minuteman High School.

To apply please submit your resume, a letter of interest, and a statement of educational philosophy to hossearch@tremontschool.org.   Please also include a personal story that illustrates a deep connection with progressive education and your ability to work with diverse learning styles and personalities; write it, use a video, or choose another method to best convey your story.  We ask that you submit three references to be contacted later in the search process.  For questions email Tim Lee at hossearch@tremontschool.org.

Leadership Opportunity
Tremont School seeks a bold, innovative leader aligned with our aspirational values. We seek an individual with a track record of building strong teams, a demonstrated commitment to collaborative work and creative curiosity about curriculum design. The best candidates will have excellent administrative talent, leadership and management skills as well as the ability to positively engage a diverse and closely connected community.

Tremont School is in its sixth year and has tremendous opportunities for growth in enrollment and funding. Offering a new educational model, it is essential that the incoming Head of School find a strong connection to our community values, and provide leadership and vision to advance the mission of the school.


Different by Design, deliberately diverse, intentionally inclusive
Students live in a changing world in which one needs to know how to constantly learn new skills and information. Tremont School is an educational community that is looking ahead to that future, preparing them for the rapidly evolving college and workplace experience and building on their personal talents. Students learn by connecting learning to the world instead of sitting behind a desk.

Tremont School is dedicated to reimagining the future of education, a future in which students feel valued and own their learning.

Tremont School was created by families seeking to change the paradigm of education. That means close attention to the intellectual, physical, social, and emotional lives of each individual so that students can learn in connected ways, where they fit in by standing out.

At Tremont School, students’ education is Customized and Connected, in a supportive, Collaborative Community that fosters creative confidence towards Transformative Outcomes.


Customized learning
Personalized. Individualized. Student-Centered. Hands-on and Hand-crafted
The best kind of learning is engaging, and built on a student’s intrinsic motivation and interest. At Tremont School, education is centered on respect for the learner, for diversity of thought, style, personality, and culture—where difference is treasured.

The science of teaching, and Tremont School’s charge, is to understand the mind of each student and their corpus of background knowledge in order to help them navigate a unique path for incorporating new information and ways of thinking into their existing understanding. Tremont School’s curriculum integrates future-oriented yet timeless explorations with a balanced process of self-discovery. In this way, students are challenged to take ownership of their own learning, and each person is encouraged to become the most successful version of him/herself.

Connected Curriculum
Interdisciplinary. Applied. Project- and Problem- Based. Integrated. Experiential.
Students need to learn in an environment that fosters joyful exploration and develops students’ natural curiosity, personal interests, and individual potential. The Tremont School Living Curriculum provides a learning environment integrating academic, social, and emotional learning. Our students connect to each other, their teachers, the broader school community, and beyond to experts in the world who understand and share their passions for particular areas of expertise.

Through projects, internships, and explorations students connect to their learning in meaningful, profound ways. The answer to the question, “Why do I need to know this?” is built into each experience, dissolving the distinction between learning and doing. With lessons growing out of the real-world, students can excel academically and personally by expanding their sense of possibility.

Collaborative Community
Inclusive. Respectful. Accepting. Supportive.
Tremont School is a safe space – where students can challenge, question, and be challenged. At Tremont School students, teachers, parents, staff, administrators, and supporters work together to foster a deep sense of belonging. Our community and the educational process, is co-created by passionate, creative students, caring teachers, and committed parents.

Transformative Outcomes
Students thrive when they feel connected to what they are learning and contribute to a community. Being at Tremont School, students find their voices, and develop inspiring levels of creative confidence and ownership of their learning. They progress academically, become prepared to meet their goals and to find their place in the world with a deep sense of belonging.

Our graduates are critical thinkers, problem solvers, and compassionate and dynamic citizens. For the right student, there is no better place. Students and families at Tremont School will both contribute to, and benefit from, our unique approach to teaching and learning.


To download pdf files further describing the Tremont School please click an icon below.

 The Tremont School Living Curriculum


Tremont in Action