Head of School
Search being conducted by The Education Group
Job Description
The Opportunity
The next Head of School will join Saint James at a pivotal moment. The School enjoys an exceptional reputation for moral formation, spiritual grounding, and close-knit community, yet faces familiar challenges shared by many small boarding schools: enrollment pressure, faculty retention, and financial sustainability. The community’s vision for the future includes preserving its Anglo-Catholic identity and family-like environment while strengthening academic rigor, expanding local and diverse enrollment, and supporting dedicated faculty. A community of balance, where academics, athletics, and the arts. flourish together. A model of Episcopal education, steadfast in faith yet responsive to the changing world.The Opportunity.
Key Responsibilities
Mission and Leadership – Serve as the spiritual, educational, and community leader of Saint James, embodying and promoting the School’s values of faith, integrity, and compassion.
Academic Excellence – Partner with faculty and administrators to sustain rigorous, relevant, and well-balanced programs that prepare students for college and life.
Enrollment - Continue to strengthen enrollment and retention by building on recent growth through strategic marketing, admissions, and development initiatives.
Advancement – Maintain and build on a strong history of successful, consecutive capital campaigns, the current Make A Difference Campaign is transforming the campus through $52 million in support for the Annual Fund, Endowment, and major capital projects.
Faculty and Staff Support – Recruit, develop, and retain exceptional educators, fostering a culture of professional growth, collaboration, and respect.
Financial Stewardship – Ensure prudent fiscal management, advance strategic planning, and cultivate philanthropic support for endowment, access, and innovation.
Community Engagement – Nurture strong relationships among students, families, alumni, faculty, trustees, and the wider Episcopal and Hagerstown communities.
Desired Professional Qualities
The Saint James community seeks a Head who is:
● Deeply knowledgeable about educational leadership and the life of both boarding and day schools.
● A proven leader, coach, and mentor who inspires confidence and growth in others.
● A strategic and forward-thinking planner, guided by sound judgment, and collaboration.
● Appreciative of the School’s Anglo-Catholic tradition and the role of faith-based education.
● Ideally, an Episcopal priest.
● Skilled in business and financial management, leading with sustainability, clarity, and vision.
Desired Personal Qualities
The Saint James community seeks a Head who is:
● Warm, approachable, engaging, and energetic.
● A strong communicator and active listener who unites people around a shared purpose.
● Fair, steady, and principled—able to make firm decisions with grace, empathy, and integrity.
● Rooted in Christian faith and guided by moral courage, reflecting the School’s enduring mission and values in both word and deed.
● Diplomatic, flexible, and attuned to the needs of all community members.
Opportunities & Challenges
The Saint James community was candid about its hopes and concerns for the coming years. The top challenges include:
1. Continuing Success with Enrollment and Visibility – Articulating Saint James’s distinctive mission to a broader audience and ensuring sustained interest from local, regional, national, and international families.
2. Maintaining Community and Tradition – Preserving the School’s family atmosphere, daily chapel, and cherished customs even as the School grows and evolves.
3. Recruiting and Retaining Faculty and Staff – Addressing workload and compensation to ensure that Saint James remains a place where teachers thrive and grow.
4. Maintaining and Strengthening the Academic Program – Ensuring rigor, balance, and relevance across disciplines, while maintaining a commitment to the whole child.
5. Controlling Costs and Enhancing Financial Health – Balancing accessibility with sustainability through thoughtful stewardship and strategic advancement.
Community Values
Saint James School is distinguished by:
● Student focused and caring faculty
● Commitment to educating the whole student
● Traditional values and the Honor Code
● Anglo-Catholic identity and daily Chapel
● Balance of academics, athletics, and the arts
“Saint James cares deeply about forming good people, not just smart ones.”
The Ideal Next Head
The ideal candidate will be a relational, mission-driven leader who:
● Leads with humility, emotional intelligence, and faith.
● Listens deeply and communicates transparently.
● Balances respect for tradition with a readiness to innovate thoughtfully. ● Champions both academic and spiritual growth.
● Inspires trust and community through integrity, warmth, and steady leadership.
How to Apply
Interested candidates should provide a résumé, cover letter highlighting their interest in and fit for the position, a statement of leadership philosophy, and a list of five (5) professional references with contact information, as a single PDF attachment, ideally by March 1, 2026. These materials should be sent to the consultants for this search listed below.
Candidates will be evaluated as materials are received.
The Education Group - Search Consultants:
Katherine Moncure Stuart - katherine@educationgroup.com
Dennis Campbell - dennis@educationgroup.com