Our Mission

Dexter Southfield helps boys and girls develop their individual talents and build an ethical foundation for life. Students learn to lead with confidence, serve with compassion, and live by the motto, "Our Best Today, Better Tomorrow."

Position Overview

The Assistant Head of School is a highly visible senior leader who works in close partnership with the Head of School and the broader leadership team to advance the mission, well-being, and strategic direction of Dexter Southfield. This role is designed for an experienced educator-administrator who understands schools as relational communities and who believes deeply in the transformative power of teaching, learning, and human connection.

The Assistant Head of School serves as a connector and capacity-builder—linking people to purpose, strategy to practice, and vision to daily school life. Rather than directing all work through a single office, this leader helps good work move through the institution by strengthening relationships, elevating collaboration, and building shared ownership across faculty, staff, and programs.

Core Responsibilities:

Leadership & Institutional Stewardship

• Partner closely with the Head of School on matters of strategy, culture, and institutional leadership.
• Serve as a key member of the School’s leadership team, contributing to collective decision-making and shared accountability.
• Act as a visible presence across campus, modeling professionalism, integrity, humility, and care.
• Represent the Head of School when appropriate and support continuity of leadership in their absence.

Academic Program & Faculty Development

• Provide leadership for the academic program with a clear focus on teaching quality, student growth, and mission alignment.
• Oversee faculty recruitment, onboarding, mentoring, evaluation, and professional growth.
• Design and support meaningful professional development rooted in reflective practice, collaboration, and continuous improvement.
• Believe deeply in relational teaching and support faculty in building strong, purposeful relationships with students.

Student Life & Community

• Support a cohesive student experience that integrates academics, athletics, co-curricular programs, and character formation.
• Promote a school culture grounded in belonging, trust, high expectations, and personal responsibility.
• Foster strong relationships among students, faculty, and families, recognizing that learning and formation occur within the community.

Strategic Initiatives & Operations

• Oversee strategic initiatives and special projects, including accreditation, long-range planning, and program development.
• Contribute to academic and programmatic budgeting and resource allocation.
• Serve on and lead committees related to leadership, academics, faculty, and student life.
• Engage with external partners and professional organizations as appropriate.

Teaching, Coaching, & School Life

• Remain actively engaged in the life of the School being present and engaged in the core functions, including teaching, coaching, advising, or other direct work with students.

Candidate Profile

The successful candidate will be an accomplished educator and administrator who brings both depth and breadth of experience across school life. We are seeking a leader who:

• Is first and foremost a great educator, grounded in teaching and learning.
• Believes deeply in relational teaching and understands the lasting impact strong teacher–student relationships have on young people.
• Has spent meaningful time as a teacher and coach, understanding schools from the inside out.
• Has experienced multiple facets of school life, including academic leadership, student life, athletics, and/or co-curricular programs, and external engagement.
• Demonstrates progressive leadership growth and commensurate experience in a senior administrative role.
• Brings sound judgment, strong decisional capital, and the ability to lead with both humility and resolve.
• Builds trust, listens well, and elevates the work of others.
• Is committed to collaboration, professional growth, and institutional stewardship.
• Possesses a deep, lived understanding of independent schools and acts with the highest personal integrity.

At the core, we seek a leader whose work will have a lasting, positive impact on students, faculty, and the long-term health and direction of the institution.

Interested candidates should submit a resume, cover letter, and list of professional references to: John Faubert, Director of Placement at Carney Sandoe & Associates  (john.faubert@carneysandoe.com) and Amanda Gastel, Placement Counselor at Carney Sandoe & Associates (amanda.gastel@carneysandoe.com). 

About Dexter Southfield

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