Head of Upper School

Orange Park, Florida, St. Johns Country Day School seeks a collaborative, student-centered educational leader to serve as our Head of Upper School for the 2027-28 School Year. This role oversees all student and faculty activities in the Upper School and fosters an environment that nurtures students’ healthy development, promotes collaboration with faculty, and advances school-wide initiatives that support the school’s mission. Successful candidates are relationship-driven leaders who balance strategic vision with strong day-to-day operational leadership. This is a full-time, in-person position for 12 months, reporting directly to the Head of School. Responsibilities

Lead the development of a culture built on high student performance, satisfaction, and enthusiasm within the division. Provide clear, mission-aligned leadership for the Upper School. Direct the activities of the various student organizations within the division. Oversee the daily operations of the Upper School. Faculty Leadership and Development. Lead efforts to build a faculty that is supportive of St. Johns’ students and families Supervise, support, and evaluate faculty within the division. Partner with the administration to strengthen instructional practices and improve student outcomes. Support recruitment, hiring, onboarding, and retention of high-quality educators. Emphasize student rigor, critical thinking, and college preparation. Support student leadership, extracurricular engagement, and post-secondary readiness.

Student Experience

Direct activities of the various student organizations and activities within the division. Set expectations for behavior guidelines, student conduct, discipline, and student development. Develop plans to meet students' educational, physical, social, and psychological needs, and ensure they are met. Promote the Upper School to new families and work to ease their transition into our community. Promote a safe, respectful, and inclusive working environment.

Curriculum & Academic Oversight

Partner with academic leaders and faculty to ensure curriculum alignment, rigor, and continuity. Support innovative teaching practices and the effective integration of technology. Monitor student performance and use data to inform decisions and program improvement.

Communication & Community Engagement

Serve as the primary point of contact for families within the division. Communicate regularly and transparently with students, parents, and faculty. Partner with Admissions and Advancement to support enrollment, retention, and community engagement. Represent the division at school events and serve as an ambassador for the school’s mission.

Operational & Administrative Responsibilities

Oversee division schedules, calendars, and logistics. Ensure compliance with school policies, procedures, and applicable regulations. Maintain accurate records of student performance, discipline, and faculty evaluation. Collaborate with the Head of School and senior leadership team on school-wide planning and initiatives.

Leadership Competencies

Strong leadership presence with the ability to build trust and foster relationships. Excellent communication, organizational, and decision-making skills. Ability to manage complex responsibilities and competing priorities with sound judgment. Commitment to fostering an inclusive, supportive school community.

Qualifications

Master’s Degree or higher; preferably in secondary education or a related field. Thorough understanding of a college preparatory program. Experience understanding Upper School students, families, and programs Collaborative experience working with the Head of School, Division Heads, Administration, and staff to achieve common goals and promote student success.

Essential Skills

Instructional and Organizational leadership Strong relationship-building Faculty leadership and development Student well-being and development Confident decision-maker Excellent communicator Commitment to the school’s mission

Work Schedule This full-time, on-campus leadership position requires flexibility to meet the needs of the school community. The Head of Upper School is expected to maintain a regular presence during the school day and to attend occasional evening and weekend events, including school programs, parent meetings, student activities, and other institutional functions. Some travel may be required for professional development, educational conferences, school-related meetings, and other activities that support the school’s mission and strategic priorities. The position is for the 2027-28 academic year. A salary commensurate with experience, degree attainment, and qualifications is paid annually. Full-time employees are eligible for our benefits package, including medical, dental, vision, disability, tuition remission, professional development/education funds, and participation in the school’s 403(b) retirement program.