Education Director

Administrator / Full-Time

Oak Meadow School, Littleton, MA

Oak Meadow School
Littleton, MA
Education Director
For July 2022

Oak Meadow School, founded in 1977, is an independent school that serves 172 students from 15-months-old through 8th Grade.  Oak Meadow is rooted in Montessori philosophy, and serves a diverse community of over 30 towns in the metro-west region of Boston, Massachusetts.

Mission:  Oak Meadow School is rooted in the child-centered Montessori philosophy, which fosters academic excellence, personal growth, and cultural awareness while nurturing children’s spirits. A diverse community of life-long learners, Oak Meadow cultivates confident, independent, and compassionate human beings by providing the tools and experiences needed to embark on rich, meaningful journeys as responsible citizens of the world.

The Education Director reports to the Head of School and is responsible for the school’s overall curriculum, including the academic, social, emotional, physical, and ethical development of students in all program levels (Beginners through Middle School) including special subjects. The Education Director is a member of the Leadership Team and oversees the Learning Team, and the hiring and supervision of all teachers and assistants, including the lower and upper program learning specialists.


Walk into any Oak Meadow classroom, on any day, and you will immediately recognize that something special is going on. From the youngest learners to those nearly ready for high school, children are completely engaged. Side by side, you will see quiet independent investigators and enthusiastic collaborators—all with an equal intensity of focus and sense of purpose. They are guided, but not directed. There is freedom, yet intentionality. There is courtesy and kindness and also a strong sense of self. There is real, relevant work going on and continual demonstrations of progress.

The teaching principles that Maria Montessori pioneered in the early 1900s are still at the forefront of progressive educational thinking today. Her research on childhood development identified differentiated approaches to learning as a key to student success, and she innovated a classroom structure that channels each child’s natural curiosity. As modern research advances our understanding of how children learn, we also advance our practice of the Montessori model at Oak Meadow. Here, you will find a program that is infused with both the spirit and architecture of the Montessori classroom experience, while preparing students for the unique challenges of our time. Every day we are constructing the foundation for a lifetime of intellectual and personal growth. When you begin here, you can go anywhere. (Academic Overview)

Oak Meadow’s educational program structure reflects its Montessori foundations:  Beginners: Toddlers (ages 15 months to 3 years), Children’s House: Early Childhood (PreK-K), Lower Elementary (Grades 1-3), Upper Elementary (Grades 4-6), and Middle School (Grades 7-8). Oak Meadow places a very strong emphasis on Social Emotional Learning. Students have the benefit of Special Subject teachers for Drama, Music, Nature, Physical Education, Spanish language, and Visual Arts,

Prospective candidates are encouraged to review with care the Oak Meadow website to gain a more comprehensive understanding of the program.

Oak Meadow is fully accredited by the Association of Independent Schools in New England (AISNE) and the American Montessori Society (AMS). It is also a member of the National Association of Independent Schools (NAIS).

The Position

The Education Director position reflects a shift in the school’s leadership structure in order to facilitate a comprehensive perspective on the academic program and consistency of faculty support and professional development.

The Education Director will join a school community in which community has been a hallmark for faculty and staff. Consistently faculty and staff members point to supportive colleagues and a culture of helping one another as the top reason for their job satisfaction. Oak Meadow is a school that highly values personal relationships, and a new Education Director needs to be an individual who authentically appreciates a professional community that characterizes itself as family. The stresses of teaching throughout Covid has taken its toll on the Oak Meadow professional community, and the Education Director will need to be skilled at supporting faculty and leading in an authentically relational, supportive, and collaborative manner.

The Education Director’s responsibilities include:

  • Develop caring, supportive, respectful, inclusive, trusting relationships with teachers and assistants.
  • Implement the school’s Collaborative Framework in order to facilitate a rich culture of engaged learning conversations and growth among all teachers and assistants as Montessori innovators.
  • Oversee the Learning Team in the articulation of overall educational goals, program goals, course objectives, materials, methods, and means of assessment.
  • Maintain congruence between the school’s board-approved Mission statement, Vision statement, North Star, and Strategy Roadmap across all educational programs.
  • Act as the educational leader of all program levels and special subjects.
  • Support and direct the activities of the school’s teaching staff in the performance of their duties.
  • Support the cognitive, social, and emotional development of students in partnership with teachers and the upper program and lower program learning specialists.
  • Work in partnership with teachers and learning specialists in planning and leading parents meetings where specific challenges related to student academic growth or social/emotional behaviors arise.
  • Function as the chief articulator of the educational programs, expectations, and behavioral guidelines.
  • Ensure compliance with legal requirements of government regulations and agencies, and maintain the educational standards established by the American Montessori Society (AMS) and the Association of Independent Schools of New England (AISNE) which examine and accredit the school.
  • Make recommendations to the Head of School regarding the hiring and retention, and the assignment of faculty.
  • Establish programs for the in-service training of all teachers, and for the evaluation of classroom teachers.
  • Keep the Head of School informed of the general programs, activities, and challenges of the school.
  • Assist in the admission process for the testing, interviewing, and evaluating of applicants for enrollment.
  • Maintain a comprehensive calendar of school events and keep the entire school community informed of various school programs and activities.
  • Oversee the coordination of all auxiliary and co-curricular programs, including the planning and the presentation of the weekly morning meeting and other programs.


Oak Meadow’s Education Director will be a knowledgeable Montessori educator and leader who authentically embraces the School’s mission and philosophy. The successful candidate will be an experienced, inspirational, and culturally competent leader who can be a visible, accessible, and good-humored presence for students, their parents, and faculty.  The Education Director will be a leader of integrity who has the self-confidence, humility, and instinct to lead in a relational manner and is adept at managing the multitude of tasks the position requires with calm efficiency and a positive manner. In addition, the ideal candidate will be:

  • A highly experienced, emotionally intelligent leader who has well-developed skills supporting, mentoring, and inspiring faculty in building a thriving professional culture;
  • Knowledgeable and able to articulate advances and trends in pedagogy and education;
  • A skillful communicator who understands the value of listening, transparency and clarity;
  • Genuinely appreciative of young children, and appreciative of opportunities to support parents in their journeys;
  • An experienced teacher who understands and values the life of a teacher;
  • Committed to diversity, equity and inclusion, with a demonstrated record of professional engagement or leadership in this arena;
  • Organized and efficient, adept at managing people, systems and structures
  • An inspiring role model who leads with passion, who delights in identifying and supporting the gifts of others, and who is comfortable bringing their whole self to work in a community that values relationships and authenticity.

For Consideration

All inquiries will be treated confidentially.  Interested individuals should send a:

  • Letter of interest,
  • Resume,
  • Short statement outlining your professional engagement with Diversity, Equity, Inclusion, and Justice work,
  • Personal statement and/or statement of educational philosophy to:

Jane Armstrong
Independent Thinking

 Anti-bias hiring practice: Oak Meadow is committed to being equitable and inclusive, providing all candidates equal opportunities to demonstrate their knowledge, skills and abilities. We welcome candidates representing the diversity of the world in our educational program, admission policies, financial aid program, staff hiring, and other school-administered programs. Our goal is to actively recruit, reach, identify, hire, promote, and retain those individuals who will best advance our school’s mission, vision, and strategic goals.

Oak Meadow School

Littleton, MA
Infant / Toddler, Early Childhood, Elementary, Middle School
All Gender