Head of School

Montgomery School is a joyful and deeply connected community where children are known, challenged and encouraged to become confident and compassionate leaders. With strong enrollment and retention, continued programmatic investment, and an engaged community, the school enters its next chapter with meaningful momentum.

About the Role

The Head of School serves as the educational leader and chief executive of Montgomery School, reporting to the Board of Trustees. The role is responsible for the overall vision for teaching and learning and the financial sustainability of the institution. The next Head of School must be committed to preserving childhood for all students and fostering a learning environment of joy and curiosity for students, faculty, and staff.

The Head of School oversees a leadership team spanning enrollment, academic programs, fundraising, finance, and operations, and is charged with communicating and amplifying the school's mission and strategic priorities into action across every dimension of school and community life.

Reporting to the Head of School are the Assistant to the Head of School, Director of Auxiliary Programs, Director of Development, Director of Enrollment Management and Tuition Assistance, Director of External Affairs, Director of Finance, Director of Operations, Family & Community Engagement Coordinator, Head of Lower School, and Head of Middle School.

About Montgomery School

Montgomery School is an independent, co-educational day school serving Preschool through 8th grade students and their families in Chester Springs, Pennsylvania. Founded in 1915, Montgomery has spent over a century perfecting the art of "preserving childhood," blending academic rigor, character development, and joyful learning.

The school's approach integrates STEAM, outdoor and environmental education, and a strong character and chapel program across a 60-acre campus. Features include a creek classroom, rain garden, fabrication lab, and walking trails through wetlands and meadows. Students engage in hands-on learning such as collecting water samples from Pickering Creek, building in a maker space with laser cutters and 3D printers, and participating in a specialized 5th and 6th grade transition program.

Montgomery maintains small classes (average of 12 to 15 students) and a tight-knit community of 323 students and 37 faculty members. The faculty represents a mix of long-term educators who have shaped the school’s culture and early- to mid-career teachers emerging as future leaders.

Responsibilities

• Preserve and enhance Montgomery’s distinctive strengths while guiding the school toward a sustainable future
• Oversee educational vision, financial sustainability, and strategic growth
• Lead and develop a leadership team across enrollment, academics, fundraising, finance, and operations
• Communicate and amplify the school’s mission and strategic priorities
• Foster a joyful, curious, and inclusive learning environment for students, faculty, and staff
• Manage budgeting, financial planning, and stewardship of institutional resources, including endowment growth
• Cultivate donor relationships and drive measurable fundraising results
• Maintain or grow enrollment while effectively communicating the value of the Preschool-8th grade model
• Invest in faculty excellence through mentorship, professional development, and retention initiatives
• Support social-emotional learning and students with learning differences
• Align educational programming with thoughtful technology integration
• Form partnerships and engage with the broader community
• Lead change while building and collaborating with a strong leadership team

Qualifications

• Record of leaving a meaningful legacy of leadership, improvement, and impact at a previous school, with preference for independent school experience
• Experience with budgeting, financial planning, and endowment stewardship
• Proven fundraising and donor-relations experience, including cultivating and soliciting donors
• Enrollment-management experience, including maintaining or growing enrollment
• Excellent written and verbal communication skills, with ability to engage diverse constituencies
• Experience investing in faculty through mentorship and professional development
• Teaching experience and understanding of faculty responsibilities
• Experience in social-emotional learning and supporting students with learning differences
• Experience aligning educational programming with appropriate technology integration
• Experience forming community partnerships and leading change
• Demonstrated executive or senior leadership experience in schools; advanced degree preferred

Personal Characteristics

• Warm, genuine, and relational with an ambassadorial mindset
• Visible and present, building authentic connections with students, families, faculty, and the community
• High integrity and transparency in communication and decision-making
• Entrepreneurial, energetic, and action-oriented
• Calm, confident, and steady under pressure
• Empowers student voice and models respectful dialogue
• Inspires trust and confidence during periods of transition
• Genuinely curious and open-minded, reflecting Montgomery’s values of critical thinking and purposeful leadership

Pay

$220,000–$240,000

Benefits

• Competitive benefits package, including comprehensive health and wellness plans
• Tuition remission
• Retirement plan with employer contribution