Head of School

The Hotchkiss School (Hotchkiss or the School), one of the top independent schools in the country, seeks an inspiring, humble, and strategic leader to join its community in the summer of 2026 as the next Head of School (Head).

Founded in 1891 and located on 827 acres in Lakeville, Connecticut, Hotchkiss has long been a beacon of academic excellence and transformative education. Today, it serves approximately 600 students in grades 9 through 12, including post-graduates, representing 31 countries and 34 U.S. states. With 96 percent of students boarding and a deeply engaged faculty, Hotchkiss offers a richly immersive educational experience. The School prides itself on small, interactive classes—averaging just 12 students—delivered by a faculty in which 72 percent hold advanced degrees and all are actively involved in student life.

Hotchkiss is a school that celebrates its traditions while embracing innovation. Under the leadership of Craig Bradley (2016–2026), the School has made significant strides in community building, financial aid, and programmatic excellence. Thirty-seven percent of students receive financial aid, and initiatives such as the Walter J. Crain Fellowship reflect the School’s commitment to inclusive leadership. Significant campus enhancements—including dormitory renovations, a library refresh, and a new Dining Commons (opening 2025)—demonstrate Hotchkiss’s investment in residential life and student wellbeing.

In partnership with trustees, faculty, staff, students, families, and alumni, the next Head will champion Hotchkiss’s distinctive identity and clarify a compelling vision for the future. They will guide strategic priorities while stewarding a vibrant and inclusive community, where students are challenged, supported, and inspired to find meaning in their lives and education. The Head will ensure operational excellence, drive innovative academic initiatives, and nurture a residential experience rooted in joy, respect, and curiosity.

The successful candidate will bring humility, intellectual gravitas, emotional intelligence, and an unwavering belief in the value of a boarding school education. They will be visible and engaged, a clear communicator and collaborative leader, able to inspire trust, navigate complexity, and make principled decisions. Experience with strategic planning, financial stewardship, fundraising, and community-building will be essential, as will a deep understanding of teaching, learning, and student development.

Inquiries, nominations, and applications (including resumes and letters of interest) should be submitted in confidence electronically below. 

Katie Rockman and Berkley Braden are leading this search with Gigi Mensah and Maria Connor. 

The Hotchkiss School is an equal opportunity employer and is committed to basing judgments concerning the employment of individuals upon their qualifications and abilities. The School is firmly committed to equal employment and advancement opportunities for all employees and applicants in all phases of the employment process (including recruitment, hiring, assignment, terms and conditions of employment, compensation, benefits, training, promotion, transfer, discipline, and determination). In accordance with applicable law, the School does not discriminate against any individual based on age, ancestry, color, genetic information, learning disability, marital status, past or present history of mental disability, national origin, physical disability, race, religious creed, sex, pregnancy, sexual orientation, gender identity or expression, veteran status, or any other protected characteristic.