Children's Tree Montessori School

Interim Head of School

Old Saybrook, CT, USHead of Department

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About This Role

About The Children's Tree Montessori School

The Children's Tree Montessori School is an independent Montessori school dedicated to nurturing a loving community of global thinkers who embrace and honor each other. Rooted in Montessori philosophy, we value kindness, integrity, respect, and a deep commitment to the development of the whole child.

We strive to create a joyful, peaceful, and emotionally safe learning environment where children are empowered to grow academically, socially, and personally. We are seeking a Head of School who will provide visionary leadership while fostering a strong sense of community among students, families, faculty, and staff.

Position Overview

The Head of School serves as the chief administrator and leader of the school, responsible for overseeing daily operations, educational programs, faculty and staff leadership, enrollment management, and community engagement. The Head of School works closely with the Board of Directors to advance the school's mission, ensure financial and operational sustainability, smooth day to day operations and support long\-term strategic goals.

The ideal candidate is a collaborative and relationship\-centered leader who has school administration experience, strong organizational and communication skills, and a commitment to child\-centered education.

Operational Leadership

Oversee day\-to\-day school operations and administration.
Supervise hiring, onboarding, evaluation, and retention of faculty and staff.
Ensure compliance with all state licensing, safety, accreditation, and regulatory requirements.
Develop and implement policies, procedures, and systems that support effective school operations.
Collaborate with the Board on strategic planning and organizational goals.

Community \& Enrollment Leadership

Serve as the primary ambassador for the school.
Build strong relationships with students, families, faculty, alumni, and community partners.
Support enrollment, retention, admissions, and family engagement efforts.
Participate in fundraising, advancement, marketing, and community outreach initiatives.
Foster a welcoming, inclusive, and collaborative school culture.

Qualifications Required

Bachelor's degree from an accredited institution.
Minimum of 10 years of school administration or educational leadership experience.
Demonstrated experience supervising faculty and staff and managing school operations.
Strong leadership, organizational, interpersonal, and communication skills.
Ability to build positive relationships with students, families, faculty, staff, and board members.
Commitment to child\-centered education and community building.
Legally authorized to work in the United States without employer sponsorship.

Preferred

Montessori teaching or administrative experience.
Montessori credential or administrator certification.
Advanced degree in education, educational leadership, business administration, or a related field.

Professional Development Requirement

Candidates without Montessori credentials must demonstrate a willingness to participate in Montessori leadership training and professional development as part of their employment.

Desired Characteristics

The successful candidate will:

Lead with integrity, empathy, and professionalism.
Be a strong communicator and collaborative problem\-solver.
Balance strategic thinking with practical day\-to\-day management.
Foster a culture of respect, accountability, and belonging.
Value the development of the whole child and the importance of strong school\-family partnerships.

Work Environment

This is an active, in\-person leadership role within a vibrant school community. The position includes campus supervision, classroom observation, family engagement, faculty support, and participation in school events throughout the year.

Application Requirements

Interested candidates should submit: