Assistant Head of School

Whitfield School, an innovative educational institution for students in grades 6-12, announces an opening for an Assistant Head of School. The assistant head of school is a full-time, 12-month position responsible for overseeing the academic, co-curricular, and signature programs of Whitfield School; ensuring vertical alignment across divisions and departments and horizontal coordination across grades; and assisting the head of school in advancing the School’s mission, vision, and strategic plan. The assistant head of school reports to the head; leads the Academic Leadership Team; is a member of the Administrative Team and Advancement Leadership Team; and supervises and supports the student-facing leadership of the School, collaborating with them to foster a positive and inclusive school culture and a strong, mission-driven school experience for students, faculty, and staff.

Responsibilities include:

Leadership and Administration

• Lead the Academic Leadership Team, supporting the group and its individual members in both the daily work of supporting students, families, faculty, and staff; and the bigger picture work of assuring the Whitfield academic experience is forward-looking, aligned with the strategic plan, and in keeping with research-based best practices.


• Supervise and support the athletic director.


• Supervise and support the director of college counseling.


• Supervise and support the director of health and wellness.


• Supervise and support the directors of the middle and upper school.


• Supervise and support the director of teaching and learning.


• Supervise and support the front desk receptionist.


• In partnership with the head of school, supervise and support the assistant to the head of school/assistant head of school.

Teams and Collaborations

• Serve as a thought partner to the head of school in designing and implementing new programs, including the initiatives articulated in the strategic plan; and assume responsibility for other projects as assigned.


• Partner with the director of equity and inclusion to promote the School’s commitment to diversity, equity, and inclusion in all aspects of school life, including hiring and retention, the academic program, school culture, and student discipline.


• Represent the student-facing leadership in the Advancement Leadership Team, ensuring their perspective is represented in that group and that the Whitfield student experience is effectively communicated in the School’s marketing, enrollment, and fundraising efforts.


• Serve as a member of the Administrative Team.


• Serve as the school’s administrative representative to MSHSAA.

Operations and Processes

• Oversee and assist in the processes for recruiting, hiring, evaluating, and supporting faculty.


• Lead and facilitate the process for creating and communicating the annual school calendar.


• Collaborate with and support the director of admission in the recruitment and retention of prospective students..


• In partnership with the Administrative Team, support the development and implementation of operational policies and procedures (handbooks, accreditation, MSHSAA, etc.) and ensure compliance with state and local regulations for schools.


• Partner with the head of school, division directors, and the director of communications and marketing in coordinating the annual process of selecting and conferring student and adult awards.

Qualities and alignment to Whitfield’s mission, vision, and values

The ideal candidate for this position possesses a deep understanding of and belief in the power of independent school education. They have a broad background in educational best practices and a clear-eyed and empathetic understanding of adolescents. They will have demonstrated the ability to lead with strength and grace while also setting high standards and expectations for excellence. They demonstrate a commitment to diversity, equity, and inclusion and a passion for helping young people discover and become their best selves. The ideal candidate is optimistic, reflective, enterprising, creative, and solutions-oriented.

In addition, the strongest candidates will possess or demonstrate the following:

Characteristics, competencies, and dispositions:

• Integrity, sound judgment, the ability to maintain confidentiality, and an ability to balance multiple perspectives.


• High emotional intelligence, strong cultural competence, and a demonstrated belief in the value of a diverse and multicultural community.


• Inspiring leadership, with the ability to model curiosity, positivity, and humility; and to build consensus and bring people together.


• Superior organizational skills, with exceptional attention to detail.


• Resilience, flexibility, energy, and enthusiasm to work simultaneously on multiple projects and manage competing priorities.


• Proficiency and comfort with academic technology.

Qualifications and experience:

• Bachelor’s degree required; Master’s degree preferred.


• Minimum seven years working experience in a school setting.


• Experience as a school leader or administrator, preferably in an independent school.


• Strong understanding of best practices in student-centered pedagogy, assessment, and curriculum design.


• Experience working with students across various ages and stages of development preferred; classroom teaching experience preferred.


• Demonstrated success setting expectations for professionalism, accountability, and collegiality.

Salary commensurate with experience. Start date is July 1, 2024.

Whitfield actively seeks to forward the equity and diversity of our community in our admissions, programming, policies, and hiring. We do not discriminate on the basis of race or color, religion, age, nationality, ethnicity, economic background, disability status, protected veteran status, sex, gender identity or expression, or sexual orientation. Whitfield School is an equal opportunity employer and we encourage all candidates to apply.