Head of School

Head of School / President Hagerstown,MD Posted Dec 12, 2025

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

• 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

• 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.

The Saint James community was candid about its hopes and concerns for the coming years. The top challenges include:

Community Values

• 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,…