Montgomery School
Head of School
Chester Springs, PA
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 in 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.
At a Glance
Mission: Montgomery School ignites each child’s love of learning and fosters their individual talents during the most formative years to prepare them for future success.
Montgomery School Promises to:
· know and challenge each child and inspire them to reach their potential
● cultivate an environment of mutual respect
● ensure a vibrant, diverse community that honors all its members
● promote the academic, social, and emotional development of each child
● promote a challenging curriculum, designed to teach students how to become critical thinkers, active problem solvers, and confident leaders
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Montgomery School Believes in:
· the power of community
● a healthy collaboration between parents and educators to support the growth and development of each student
● creating an enriching cultural environment which promotes inclusion and belonging
● character development and teaching the importance of personal integrity, respect, responsibility, and service to others
● preserving childhood for Preschool through 8th grade students
Facts and Figures
Founded: 1915
Enrollment (2026-27): 323
School Employees: 59 total; 37 full-time faculty, 65% of whom hold advanced degrees
Average Class Size: 12 students (Early Childhood Center), 15 students (Lower & Middle School)
Diversity: 25% of students come from racially and ethnically diverse backgrounds
Operating Budget: $6.9M
Tuition:
Preschool (Half Day-Full Day): $13,390-$19,465
PreK (Half Day-Full Day): $17,510-$23,665;
Kindergarten: $25,750
Grades 1-4: $28,840
Grades 5-8: $31,000
Financial Assistance: $2.7M awarded
Total Funds Raised in 2025-26: $825,000
Parent Participation in Annual Giving: 58%
Physical Plant: 60 Acres
Ten-year Accreditation: Pennsylvania Association of Independent Schools (PAIS); 2026
Artificial Intelligence Program Endorsement: Middle States Association of Colleges and Schools (MSA); 2025
On the Web: https://www.montgomeryschool.org
Strengths of the School
Montgomery's next Head of School will inherit a school in a genuine position of strength: a clear mission, engaged and committed families, an excellent faculty, and an energetic and supportive Board of Trustees who embrace the priorities for the future.
Community. Montgomery’s greatest strength is its community. Drawing students from 75 zip codes and nine school districts, the school brings together families, faculty, staff, trustees, and students around a shared commitment to preparing young people to think critically, lead purposefully, and contribute with confidence. Ask students, families, faculty, staff and alumni about Montgomery, and the anecdotes come pouring out. Stories that speak to the strength and warmth of the community are consistent, each of them influenced by the relational experience of being known. Montgomery is consistently described as a place where every child is deeply valued and genuinely cared for. At its heart, this is a community where children are seen not only for what they achieve, but for who they are. Families, faculty, and staff all speak of a culture that feels welcoming, personal, and nurturing, creating a sense of connection and belonging that leaves a lasting impression on students long after they have moved on.
This spirit of connection is woven into the fabric of daily life. Whether gathered around family-style lunches, building friendships through cross-grade buddy relationships, or coming together for traditions, such as Greek and Roman Games that culminate the year, students experience the joy of belonging to something larger than themselves.
One of Montgomery's most cherished traditions is Chapel, a non-denominational gathering originating on its founding campus in Wynnewood, PA. Three mornings a week, students, community members, faculty, and staff lead and listen to announcements, celebrate birthdays, and hear presentations from one another and outside speakers. A culminating graduation requirement, 8th graders regularly lead chapel and deliver a "chapel" on a topic meaningful to them. The Preschool-8 model further strengthens these bonds, creating a close-knit community where younger students are inspired by older ones and older students embrace meaningful opportunities to mentor, lead, and care for those who follow in their footsteps.
Academics. Montgomery, often affectionately referred to as Monty, stands out among its peers for its commitment to nurturing the whole child. Through outdoor education, character development, the arts, theater, leadership experiences, and a strong emphasis on student voice, children are encouraged to discover their unique strengths and passions. They develop not only academically, but also emotionally and socially, gaining confidence, resilience, curiosity, and independence along the way. Families deeply appreciate an environment that challenges students while also preserving the wonder, imagination, and joy of childhood, allowing children to grow into thoughtful, capable young people without ever losing sight of what makes these years so special.
In Lower School, The Early Childhood Center houses the youngest learners in two distinctive programs, both offered as half-day or full-day. In The Playhouse Preschool, children ages 3-4 engage in a play-based curriculum rooted in the fine arts through Montgomery’s relationship with SALT Performing Arts. In full-day PreK, programming emphasizes social-emotional development, helping children navigate new experiences with confidence, self-awareness, and sensitivity to others. These young learners build academic, social, emotional, and creative skills through joyful, hands-on learning.
In Grades K-4, students constantly apply new knowledge while developing a stronger sense of self, awareness of others, and confidence in who they are becoming through special features like family-style lunch and weekly community gatherings. Students explore language arts, math, Spanish, social studies, and science while practicing mindfulness, and learning outdoors with access to the entire 60-acre campus.
Montgomery’s thoughtfully guided environment supports their intellectual, social, and physical growth at each developmental stage, recognizing that children are still growing rather than “finished products.”
In Middle School, Grades 5-8, there is a balanced, whole-child approach that stretches academic expectations while helping students discover their talents, interests, and voices. Students seize opportunities to take on more through voice, agency, leadership roles, buddy mentoring, teacher- or student-led electives, and clubs, while exercising the strong character that accompanies effective leadership in all walks of their middle school lives. The PreK-8 school environment allows teachers to genuinely learn about and connect with students, fostering trusting relationships that help them see challenges as opportunities to learn. By cultivating a safe environment and a sense of belonging with peers and teachers, Montgomery supports middle schoolers’ emotional well-being and success while preparing them for secondary school with strong habits of mind, body, and character.
Dedicated Faculty. At the center of this experience are Montgomery's dedicated faculty and staff. Their compassion, expertise, and enduring commitment to the school's mission create a culture of trust, continuity, and care. They know their students well, celebrate their successes, support them through challenges, and help each child feel safe enough to take risks, explore new possibilities, and discover their potential. The strong relationships among students, families, and educators create a genuine sense of partnership rooted in mutual respect and shared purpose.
Strategic Framework
In early 2024, the Montgomery Board and Head of School asked its community, "What does it look like to be future-ready?"
Answer: Future-ready means building our capacity to adapt and be responsive to changing circumstances, known and as-yet-unknown.
The Board subsequently adopted a strategic framework centered on its existing values and investing resources to ensure the school's future thriving. Having divided the framework into annual tactics, the school is celebrating meeting its many ambitious goals in the first two years. These included adding additional counseling resources; adoption of a new character education framework; the formation of an alumni association; the creation of a school wide Inclusion and Belonging Statement; Board adoption of a “Green Mission Statement” and development of additional environmental education areas throughout the campus; and, enhancing advancement staffing and EITC (Educational Improvement Tax Credit-Pennsylvania) fundraising strategies. This fall, the Board and leadership are setting their sights on the next set of tactics to sustain Montgomery’s momentum. The framework is built on these four pillars and respective strategies:
Advance Our Programs
● Lead in student-centered education through innovative, responsive teaching that responsibly integrates emerging technologies, AI, and real-world challenges
· Develop confident, inclusive leaders through interdisciplinary learning and experiences that build character, well-being, and readiness for a changing world
Prioritize our People
· Invest in exceptional people by supporting faculty and staff well-being, growth, and learning while attracting innovative educational leaders
● Strengthen a connected community by fostering belonging, engaging families and alumni, and building relationships that enrich the Montgomery experience
Steward Our Place
· Sustain and enhance Montgomery’s campus through responsible stewardship, strategic facilities planning, modern technology, and sustainable practices that support long-term growth
● Use the campus as a living laboratory for environmental responsibility, linking academics, outdoor learning, and community engagement while caring for the school’s land, resources, and neighborhood
Innovate Our Platform
· Expand Montgomery’s impact through community engagement, strategic partnerships, and innovative programs that extend its mission beyond campus
● Strengthen financial resilience and visibility through fundraising, new revenue opportunities, and broader use of Montgomery’s resources, facilities, and brand identity
The next Head of School will have the opportunity to partner with the Board as they complete the final two years of the strategic framework, elevate their ambitions for a successful close, and roll up their sleeves to partner on what's next. This is an opportunity for a leader who can deepen Montgomery's academic and character-education program, sustain its strong sense of community, and champion an already well-regarded school as it reaches an even wider pool of families across the region. Montgomery's next Head of School will inherit a school in a genuine position of strength: a clear mission, financially engaged families, an excellent faculty, and an energetic and supportive Board of Trustees who embrace the priorities for the future.
Opportunities and Challenges
Even as Montgomery leverages these strengths, school and board leadership are aligned on the strategic priorities ahead for the school.
Preserving Montgomery’s Magic
Chief among Montgomery’s priorities is preserving the school’s distinctive culture: a combination of exceptional, singular learning opportunities found within a warm, cohesive, and diverse community. The next Head of School will be called upon to preserve these traditions of personal connection, student independence, visible leadership, chapel programs, and student leadership opportunities while guiding the school through continued growth and change.
Financial Sustainability and Enrollment
Montgomery has made meaningful progress in strengthening its enrollment and financial position. A tuition reset in 2018 followed by expanded early-childhood programming through the school’s partnership with SALT Performing Arts and increased retention rates have all contributed to historic and remarkable enrollment growth from 220 to more than 320 students in seven years.
Like many independent schools, Montgomery faces the challenge of bridging the gap between tuition revenue and the true cost of educating each child. It also operates in a competitive market and without a substantial endowment. The next Head will build on the School’s positive momentum by clearly articulating the value of a Montgomery education and deepening a growing culture of philanthropy. In addition, they will partner with the school’s newly hired Director of Auxiliary Programs to develop additional sources of revenue. This work will ensure that future growth remains mission-aligned and financially sustainable.
Program, Students, and Faculty
Areas of progress and opportunity include expanding support for students for the diverse learning needs of our student body, attending to faculty retention and recruitment, and guiding Montgomery’s approach to emerging technology-related issues, including artificial intelligence policies. The next Head should also continue supporting students’ social-emotional development.
Montgomery’s dedicated faculty and staff are central to the strength of the school. At the same time, Montgomery operates in a competitive regional market driven by competition from local independent and public schools. The school is focused on enhancing recruitment and retention through improvements in compensation and benefits as well as professional development and opportunities for leadership and growth. While meaningful work in progress is leading to strong results, the next Head will build on these efforts while fostering a culture in which educators feel supported and empowered to thrive.
Governance, Leadership, and Transition
The Board maintains clear governance boundaries and is committed to a collaborative partnership with the Head of School grounded in trust, transparency and mutual support. The next leader will benefit from this foundation while providing continuity during the leadership transition, building on the School’s current strategic and financial plans, and working effectively with current leaders.
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
Key Competencies
The ideal candidate for the Head of School position possesses the following competencies:
● Communicates Effectively: Communicates clearly and effectively through multiple channels, tailoring messages to meet the unique needs of different audiences
● Instills Trust: Builds trust and credibility through honesty, integrity, authenticity, and consistent actions
● Drives Vision and Purpose: Articulates a compelling vision and strategy that inspires, motivates, and aligns others toward shared goals
● Embraces Purpose-Driven Decision Making: Makes sound, timely decisions based on available information, enabling progress and organizational success
● Collaborates: Builds strong partnerships and works collaboratively across teams to achieve shared objectives and deliver results
● Applies Big Picture Thinking: Takes a broad, strategic view when approaching issues, applying a global lens to understand impact, identify opportunities, and drive effective solutions
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