Head of Upper School

                                    Head of the Upper School-Keystone School

Keystone School helps bright, talented and motivated young people realize their full potential. In our academically accelerated program, faculty and staff challenge and nurture young people throughout their educational journey. Keystone students achieve in academics, arts, sciences, athletics and other diverse interests, while supporting and challenging each other. As students grow from preschool through high school, expert and caring teachers guide their inquiries. Keystone students gain admission to the country’s most prestigious colleges and universities, win highly competitive scholarships, and go on to create fulfilling careers and lives.

Keystone School seeks a devoted, inspiring, and compassionate individual to lead its Upper School.  Ranked as Alamo City’s number one college-preparatory school, Keystone’s high school deftly balances academic challenge with a broad-based extracurricular program, a diverse and close-knit student body, and an emphasis on student well-being. 

Working closely with other administrators and a dedicated and caring faculty, the Head of the Upper School will oversee all aspects of the high school program while continually seeking out areas for improvement.  

The Upper School is well-positioned for a new educator to lead from a position of strength while recognizing that we can always get better. 

Qualifications include:

Required:

A Master’s Degree

Experience in educational leadership

Teaching experience

Demonstrated strong written and speaking skills

Preferred:

Experience working in independent schools

Head of the Upper School

The Division Head reports to the Head of School and serves on Keystone’s Administrative Council. The Head of the Upper School is charged with the comprehensive responsibility for all activities involving students and faculty of the upper school. This position requires strong listening and positive communication skills. The specific responsibilities include the following:

Leadership and School Culture 

• To maintain congruence between the school’s board-approved mission statement and all activities of the division.

• To foster an Upper School community of students and faculty that values individual growth, achievement, and character building.

• To act as the educational leader of the Upper School, including:

• Responsibility for its day-to-day operation;

• Directing the activities of the members of the instructional staff

• Clearly articulating the division’s programs, expectations, behavioral guidelines, and other information necessary to ensure that all constituencies are fully informed consistent with their individual roles.

• Being a visible presence in all areas of the division; to work toward a resolution of all problems - both routine and unique - as they arise; to keep the Head of School informed of the general programs, activities, and challenges of the division.

• Attending extracurricular events to demonstrate investment in the Keystone community.

• Developing and driving parent partnerships with Keystone. This includes outreach and parent education as well as community building.

• Overseeing the school’s highly regarded Outdoor Education and Travel Society programs. 

Faculty Support  

• To observe, supervise, and help evaluate the faculty in the development and implementation of curriculum and to review and evaluate the academic programs.

• To serve as a consultant to teachers in matters of classroom management, teaching methods, and general school procedures.

• To create and maintain an educational environment in which learning can take place,  a climate which is supportive, and reflects high morale.

• To make recommendations to the head of school regarding the hiring, retention, and assignment of faculty;

• To establish programs for the orientation of new teachers, for in-service training of all teachers, and for the evaluation of classroom teachers,

• To ensure that teachers are familiar with and adhere to school policies and best practices in all areas of the operation.

• To oversee course scheduling, registration and coordinating the purchase of textbooks.

Student Support

• To be aware of the educational, physical, social, and psychological needs of the members of the high school community and develop plans for meeting these needs.

• To broaden the scope of innovative opportunities, including signature and cross-disciplinary experiences, experiential programming for students, and community partnerships.

• To oversee the coordination of the co-curricular and extra-curricular activity programs of the division; to assist in the planning and presentation of assemblies and advisory programs; maintain a comprehensive calendar of events; keep the entire community informed of various school programs and activities.

• To provide for the academic guidance of students; to oversee the grading and reporting of standards and methods used by teachers in measuring student achievement.

• To be responsible for establishing guidelines for proper student conduct and dress; to maintain student discipline consistent with school policies; to monitor students’ adherence to established rules; to maintain accurate records of student attendance and citizenship.

• To partner with the Upper School counselors and faculty to ensure socio-emotional programming and that Keystone lives its philosophy of  “Doing well by being well.”

 Other

• To actively recruit new students in partnership with the Director of Enrollment Management and re-recruit current students, particularly from middle school to upper school. To assist in the admission process for the testing, interviewing, and evaluation of applicants for enrollment in partnership with the Director of Enrollment Management.

• To perform other duties as assigned by the Head of School.

Competitive salary and benefit package.

Interested candidates should submit a cover letter, resume, and contact information for three to five references to Michael Flynn at mflynn@keystoneschool.org by Friday, October 23, 2026. 

We recognize that diverse teams make the strongest teams, and we encourage people from all backgrounds to apply. We do not just accept difference–it's one of our key values.

Keystone School welcomes candidates for admission or employment, regardless of age, race, culture, gender, sexual orientation, religion, socio-economic status, national or ethnic origin, and does not discriminate on the basis of any category protected by law in the administration of any of its programs.

For more information about Keystone School, please visit www.keystoneschool.org