Montessori Head of School - Boston Area

Head of School – Montessori School Director

Location: Boston, MA Job Type: Full-time, year-round Schedule: Monday to Friday Pay: Starting at $85,000 per year Base Salary Range: $85,000–$95,000 per year Performance Bonus: Up to $10,000 annually, with quarterly payouts Work Location: In person

At Illuminate Montessori, the Head of School serves as the instructional, operational, and community leader of the school. The Head of School is responsible for creating a warm, high-quality Montessori environment where children are known, families feel connected, and staff are supported in their growth.

We are building a network of high-performing Montessori schools designed to redefine what excellent education looks like. We believe children thrive in environments that foster independence, confidence, and purpose, and we are committed to expanding access to high-fidelity Montessori programs across our communities.

This is a full-ownership leadership role. The Head of School is the leader of the campus and is responsible for driving enrollment growth, team performance, program excellence, operational quality, and financial success.

This role is ideal for an experienced, driven early childhood or school leader who is deeply committed to Montessori philosophy, values collaboration, leads with urgency and composure, communicates with professionalism, and embraces continuous growth.

At Illuminate Montessori, we live our values every day:

The Child Always Comes First
We protect each child’s right to independence, dignity, and development at their own pace.

Commitment to Partnering with Families
We believe education is strongest when school and home work together.

Be a Swan
We lead with calm professionalism, even in challenging moments.

Embrace Growth
We reflect, receive feedback openly, and commit to lifelong learning.

The Head of School is responsible for leading a thriving Montessori school community with ownership, accountability, and vision.

We are looking for a leader who has the talent, urgency, and perseverance to:

• Build and lead a strong team
• Create a thriving school community
• Deliver an exceptional educational experience for every child
• Drive enrollment growth and family retention
• Maintain operational and licensing excellence
• Support the financial health and long-term success of the campus

Candidates must:

• Meet all Massachusetts EEC requirements for Director (non-negotiable)
• Hold at least a Bachelor’s degree
• Have at least 3 years of school leadership experience
  , such as Director, Principal, Head of School, Program Director, or Administrative Leader
• Complete and maintain all required EEC trainings, including but not limited to:
• First Aid & CPR Certification
• EEC Essentials 2.0 Certificate
• Successfully pass all required background record checks, including BRC
• Demonstrate strong organizational, operational, and people leadership skills
• Demonstrate a proven ability to lead teams, drive results, and communicate effectively

Preferred candidates may also have:

• Montessori experience or certification, such as AMI, AMS, or MACTE
• Early childhood education leadership experience
• Experience in admissions, enrollment growth, or school operations
• Experience managing budgets, staffing models, labor efficiency, or campus-level performance goals
• A background as a School Director, Program Director, Head of School, Principal, or Administrative Leader

• Develop and execute a strategic plan for the campus
• Build a culture aligned to mission, accountability, professionalism, and excellence
• Lead with ownership, composure, urgency, and strong decision-making
• Represent Illuminate Montessori’s mission, values, and standards across all areas of school life
• Partner with organizational leadership to support school growth, quality, and long-term success

• Uphold a beautiful, calm, safe, and welcoming Montessori environment across the school
• Ensure classrooms reflect strong Montessori practice, developmentally appropriate expectations, and consistent routines
• Part…