Head of School

Montgomery School; Chester Springs (PA); On-site; USD 220,000 - 240,000; Full time

Benefits offered by this job

Tuition remission

Health and wellness plans

Retirement plan with employer contrib.

Job summary

Montgomery School in Pennsylvania seeks a thoughtful, inspiring Head of School to lead teaching and learning, and to ensure financial sustainability. The role oversees a leadership team spanning enrollment, programs, development, finance, and operations.

The Head will preserve childhood, foster joy and curiosity, and guide sustainable growth and community engagement. The successful candidate will bring senior leadership experience in independent schools, strong communication skills, and a

Qualifications

• Experience leading independent or similar schools.
• Experience budgeting, financial planning, and stewardship of resources (endowment).
• Fundraising and donor-relations with measurable results.
• Enrollment-management and communicating school value.
• Excellent written and verbal communication across diverse groups.
• Mentorship and development of faculty.
• Teaching experience and understanding of faculty responsibilities.
• Experience in social-emotional learning and supporting learning differences.
• Aligning curriculum with thoughtful technology and innovation.
• Building partnerships with the community.

Responsibilities

• Serve as educational leader and chief executive, guiding teaching and learning.
• Oversee leadership team across enrollment, programs, fundraising, finance and operations.
• Communicate Montgomery School’s mission and priorities into action.
• Preserve childhood and foster joy, curiosity, and sustainable growth.
• Lead change while building a strong leadership team and partnerships.

Skills

Leadership experience

Budgeting and financial planning

Fundraising and donor relations

Enrollment-management

Excellent written and verbal comms

Faculty mentorship and development

Teaching experience

Social-emotional learning

Technology integration in education

Community partnership development

Change leadership

Executive leadership in schools

Education

Advanced degree in education or related field

Job description

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

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

The Opportunity

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 2026-2027 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.

Background

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.

The Position

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.

Desired Qualifications and Qualities

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.

Education, Experience, and Skills

• A record of leaving a meaningful legacy of leadership, improvement and impact at a previous school, with a preference for experience in or knowledge of independent schools
• Experience with budgeting, financial planning, and stewardship of institutional resources, such as building and sustaining an endowment
• Fundraising and donor-relations experience, including proven ability to build relationships, cultivate and solicit donors, and demonstrate measurable fundraising results
• Enrollment-management experience, including maintaining or growing enrollment and communicating the value of the school’s Preschool-8 educational model
• Excellent written and verbal communication skills, with the ability to engage credibly and authentically across a wide range of constituencies
• Experience investing in faculty excellence through mentorship, professional development, and initiatives that promote long-term engagement and retention
• Teaching experience and an understanding of faculty responsibilities
• Experience in social-emotional learning and supporting students with learning differences, including leading and developing faculty and staff in these areas
• Experience with aligning educational programming with thoughtful and appropriate technology, preparing students for a rapidly changing world while protecting and fostering their human development
• Experience forming partnerships and engaging with the broader community
• Experience leading change while building and working effectively with a strong leadership team
• Demonstrated ability and experience in an executive or senior leadership role in schools; advanced degree preferred

Personal Characteristics

• Warm, genuine, and relational with an ambassadorial mindset; able to build trust quickly across a close-knit community
• Visible and present, building genuine personal connections with authentic enthusiasm for engaging students, families, faculty, and the surrounding community
• High integrity and transparency in communication and decision-making
• Entrepreneurial and energetic, with a bias toward action
• Calm, confident, and steady, both under pressure and at peace
• Empowers student voice and action, with a leadership style that models and inspires respectful dialogue
• Ability to inspire trust, confidence, and community support during periods of transition
• Genuinely curious and open-minded, reflecting the values of thinking critically, leading purposefully, and contributing with confidence that Montgomery seeks to instill in its students

Compensation and Benefits

Salary and Benefits

$220,000-$240,000; Competitive benefits package, including comprehensive health and wellness plans, tuition remission, and retirement plan with employer contribution

Application Requirements and Search Process

DRG is conducting this search on behalf of Montgomery School. Interested candidates should submit, as soon as possible, materials including the following:

• A cover letter indicating why they are particularly interested in and qualified for the position;
• A current resume;
• A one-to-two-page writing sample of a communication (newsletter, parent or faculty communication, address, or speech) in PDF format; and
• Five references and their contact information (names, email addresses, and phone numbers), as well as the relationship of each reference to the candidate. References will be contacted only at the finalist stage and with the candidate’s permission.

Application Status: Accepting Applications

Start Date: July 1, 2027