The Taft School – Watertown, Connecticut
Start Date: July 01, 2026
Posting Date: November 01, 2025
Position Type: Full-Time, 12-Month

The Search

The Taft School (Taft), one of the nation’s premier college-preparatory boarding schools, seeks a strategic and student-centered leader to serve as its next Assistant Head of School for Student Life. This senior leadership role is a distinctive opportunity for an experienced educator to lead and empower a team of professionals in shaping a comprehensive student life program that reflects Taft’s core values—learn deeply, build purpose, serve generously, pursue excellence, lead with courage and support students in developing the outcomes in Taft’s Portrait of a Learner.

The Assistant Head will be both an architect and team leader, guiding the Student Life Team which includes Deans, Directors, and other student-facing colleagues to build systems and structures that equip others to do transformative work with students. While they will engage with individual student matters, their primary purpose is to empower and support the people who support students, fostering a culture of collaboration, mentorship, and shared leadership.

In partnership with the Head of School, the Assistant Head for Faculty and Academics, and a deeply committed leadership team, the Assistant Head will advance a student experience that is joyful, inclusive, and transformative, preparing Taft students to be ethical and empathic citizens, curious and critical thinkers, and resilient leaders who live lives of integrity, purpose, and impact.

This moment in Taft’s history is one of reflection and renewal. As we move forward with our strategic plan and deepen our commitment to our Core Values and Portrait of a Learner, the Assistant Head will play a central role in shaping the daily culture and long-term vision of student life at Taft.

Founded in 1890 by Horace D. Taft, the School has long held that character, above all else, determines success in life. Today, Taft students, known affectionately as “Tafties”, embody the School’s motto, Not to be served, but to serve, through meaningful engagement in communities surrounding campus and contributions to global inquiry. Taft’s 590 students benefit from a rigorous academic curriculum, exceptional faculty, and a vibrant campus life that fosters personal growth and lifelong friendships.

As a well-resourced and forward-thinking institution, Taft continues to invest in its mission. Our commitment to diversity and inclusion is reflected in its student body: 42 percent of students identify as students of color, 19 percent are international students from 54 countries, and 35 percent receive financial aid. With a strong endowment of $367 million and an operating budget of approximately $54 million, Taft is well-positioned to sustain excellence and improve continually.

Overview

Reporting directly to the Head of School, the Assistant Head will lead a cross-functional team of educators and student life professionals to cultivate a residential and co-curricular environment that is safe, joyful, and purpose-driven. Through their work with the team, this leader will ensure that every student is known, supported, and empowered to grow in alignment with Taft’s Portrait of a Learner, Core Values, and emerging Principles of Learning.

Key Responsibilities

Strategic Leadership Responsibilities

• Vision and Strategy: Advance a cohesive and future-focused student life strategy that reflects Taft’s 2030 Strategic Design, addressing the evolving needs of adolescents in an age of AI, ever-increasing complexity, and national and global change.
• Integration and Alignment: Lead the Student Life Team to ensure that residential life, wellness, discipline, leadership development, advising, school meetings and community meals, clubs, student activities, and co-curricular engagement are intentionally aligned with Taft’s mission, values, and educational philosophy.
• Culture and Community: Foster a campus culture rooted in empathy, moral leadership, creativity, and resilience—qualities essential for flourishing in today’s world.
• Innovation and Design: Collaborate with academic and operational leaders to design and assess student life programs that support the development of unique human capacities and prepare students to learn and embody Taft’s Portrait of a Learner.

Core Responsibilities

• Lead and manage the leaders of all aspects of student life, including residential life, wellness, discipline, leadership development, advising, school meetings and community meals, clubs, student activities, and co-curricular engagement.
• Lead response, in coordination with relevant colleagues, to student-related emergencies.
• Partner with faculty and staff to ensure that learning and growth extend beyond the classroom and into all aspects of campus life.
• Serve as a key architect of the student experience outside of the classroom, ensuring it is developmentally appropriate, inclusive, and aligned with Taft’s strategic priorities and educational vision.
• Champion student voice and agency, creating opportunities for leadership, service, and meaningful community engagement.

Direct Reporting Relationships

• Student Life Team
• Office of Student Life, including Dean of Students, Associate Dean of Students, Dean of Residential Life, and Activities Coordinator
• Chaplain
• Counseling Department 
• Health Center (non-compliance related)
• Class Deans

Member of

• Senior Administrative Team
• School Meetings Team
• Emergency Response Team
• Overseer of Taft Calendar
• Staffs the School Performance Committee in partnership with Assistant Head for Faculty & Academics

Ideal Candidate Profile

• Experienced boarding school educator and leader with deep experience in all aspects of student life
• Strategic thinker who can translate vision into action and lead change across complex systems.
• Exceptional interpersonal and communication skills, with a collaborative and empathetic leadership style.
• Demonstrated commitment to whole-child education and adolescent development.
• Commitment to collaborating with colleagues to create diverse and equitable communities of belonging. 
• Deep understanding of the challenges and opportunities facing adolescents today, including the impact of technology, social media, substance use, and cultural shifts.
• Passion for boarding school life and a belief in the transformative power of boarding–for community, relationships, and character education.

Taft is committed to creating a learning environment where students are cared for, challenged, and inspired to become their best selves.  With a legacy of excellence and a bold vision for the future, Taft offers a unique opportunity for leaders to shape the lives of young people in profound and lasting ways.

The Taft School is an equal opportunity employer committed to building a diverse and inclusive community. We encourage applications from candidates who will contribute to our school’s diversity and support our mission of developing engaged, thoughtful, and confident young people.

For questions about this search, please contact Maya Drye, Recruitment Manager for The Taft School at mdrye@taftschool.org.

Key Qualifications

Experience & Background

• Minimum five years of experience in boarding school environments.
• Proven leadership in student life, residential life, or related areas.
• Experience managing cross-functional teams and complex operations.
• Background in crisis response, student support, and inclusive community building.

Personal Attributes

• Decision maker and thought partner
• Collaborative and empowering leadership style.
• High emotional intelligence and sound judgment.
• Adaptable and calm under pressure.
• Warm, approachable, and student-focused.
• Strong personal integrity aligned with Taft’s mission.

Preferred Qualifications

• Master’s degree 
• Experience with strategic planning and implementation.
• Background in restorative discipline or community-building practices.

Position Details

• Reports To: Head of School
• Schedule: Full-time, with evening and weekend presence required
• Housing: On-campus or near-campus housing available
• Start Date: July 01, 2026 
• Compensation: Competitive salary and benefits package

Application Process

Interested candidates should submit the following to mdrye@taftschool.org:

• Cover letter
• Resume/CV
• Contact information for three professional references

In your cover letter, please address:

• Your philosophy of student life in a boarding school environment
• Specific examples of team leadership and community building
• Your approach to implementing strategic initiatives across departments
• Your vision for integrating all aspects of the student experience

About The Taft School

Founded in 1890, The Taft School is a boarding school for 600 students in grades nine through post-graduate. Living where they learn, academically talented students from all over the world are guided by an extraordinary faculty on a 220-acre campus in western Connecticut. With the motto “Not to be served but to serve” as a foundation for the inclusive and service-minded community.

Connections working at The Taft School