Head of School

Montgomery School is pleased to partner with DRG to conduct this search.

This is an abbreviated description. Please read the full Opportunity Statement HERE.

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.

Tom McManus, Montgomery’s Head of School since 2020, will conclude his tenure at the end of the  school year. Under his leadership, Montgomery successfully navigated the pandemic and experienced significant growth, including increased enrollment, expanded programming and campus enhancements – including completion of the Innovation Center and new baseball field. Montgomery seeks a thoughtful and inspiring leader who will honor the school’s distinctive strengths, build on its momentum and guide it toward a sustainable future.

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

Montgomery's approach blends STEAM, outdoor and environmental education, and a strong character and chapel program across a 60-acre campus that includes a creek classroom, rain garden, fabrication lab, and walking trails through wetlands and meadows. Students collect water samples from Pickering Creek, build and tinker in a maker space stocked with laser cutters and 3D printers, take part in a specialized 5th and 6th grade transition program, and grow as critical thinkers, active problem solvers, and confident leaders, all within small classes (an average of 12 to 15 students) and a tight-knit community of 323 students and faculty.

Montgomery’s 37 faculty members represent a mix of long-term faculty who have helped create the school’s strong culture and early- to mid-career teachers who are emerging into leadership for the future.

Reporting to the Board of Trustees, the Head of School serves as the educational leader and chief executive of Montgomery School and 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 its 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.

The ideal leader will pair a genuine belief in the Preschool-8th grade educational model with a deep, demonstrated respect for the journey of childhood for students, their caregivers, and their teachers. They will demonstrate the strategic and financial acumen to manage an organization with diverse stakeholders experiencing the benefits of sustainable, intentional growth, and an environment that fosters innovation and continuous improvement.

As is expected of faculty and staff at Montgomery, its successful leaders value thinking boldly, solving creatively, and leading compassionately in the service of children as both a mindset and a persistent aspiration.

• A record of leaving a meaningful legacy of leadership, improvement and impact at a…