The Walter Crain Fellowship program is a partnership between The Hotchkiss School and the Klingenstein Center at Teachers College, Columbia University. The program honors Walter Crain, the first African-American educator and administrator at the Hotchkiss School. Walter Crain was an educator known for his care and devotion to students and the School. Hotchkiss seeks to attract individuals who have demonstrated a commitment to working with diverse and/or historically underrepresented populations in education and who are inspired to pursue leadership careers in schools. The fellowship appointment begins July 1, 2026, with on-campus responsibilities beginning in August.

Appointed for three years, Crain fellows will divide their time between teaching responsibilities and administrative work within one of our main administrative departments (admissions, college advising, alumni and development, pluralism and community, dean of faculty, dean of students, or the business office) and will also pursue a Master’s degree in Private School Leadership in collaboration with the Klingenstein Center. As a complement to the mentorship provided by the Klingenstein program, each Walter Crain Fellow will have mentors within the Hotchkiss community. During their three-year tenure, Crain Fellows will participate actively in all aspects of community life through service in Hotchkiss’ residential, advising, and co-curricular programs. 

Hotchkiss is located in the scenic Berkshire-Taconic landscape, in the quiet northwest corner of Connecticut. The Hotchkiss School is a community where faculty and staff build careers and grow as professionals. We seek to identify, recruit, and develop faculty and staff members who bring diverse experiences, perspectives, talents, and backgrounds. Collectively, we are dedicated to supporting the intellectual, social, and emotional growth of 620+ students who come from around the world.

In the 2025-2026 school year, our student body includes 17% international students, 41% domestic students of color, and 34% of students receiving financial aid. Geographically diverse, our students represent 35 U.S.states, 32 countries, and span 5 continents. The School is eager to accept applications from individuals who are excited to support an inclusive, warm learning community for students from diverse backgrounds and experiences.

Qualifications:

The ideal Walter Crain Fellow will be an educator with at least five years of professional experience in a school or higher education setting. They will aspire to be leaders and mentors and will demonstrate, or have a strong interest in developing, deep cultural competencies in themselves and others as part of their approach to leadership and community building. Successful candidates will have a demonstrated ability to make authentic connections with BIPOC (black, indigenous, and people of color) students and colleagues. Candidates with experience in English, Spanish, Mathematics, and Science (all fields) are strongly encouraged to apply. 

Duties & Responsibilities:

Hotchkiss faculty participate actively in all aspects of community life through service in Hotchkiss’ residential, advising, and co-curricular programs. Typical responsibilities of a Walter Crain Fellow include teaching and administrative duties, coaching for one season on a co-curricular team or the equivalent, regular duty in our residential program, and participation in a robust mentoring program. Full-time faculty members are generally expected to obtain a public service endorsement on their CT driver’s license within the first year of employment, so that they may drive students in school vehicles.

Compensation:

Salary is competitive and commensurate with experience and education level. In addition to housing, Hotchkiss provides a comprehensive benefit package that includes a variety of health insurance offerings, dental, vision, and life insurance, short- and long-term disability, HSA/FSA options, and retirement benefits through TIAA. Fellows accepted into the Klingenstein program receive full tuition paid by Hotchkiss while they are employed. 

Ample funding exists to support participation in professional conferences, workshops, and travel. Faculty are encouraged to enjoy meals in our dining hall while school is in session. Tuition at Teachers College, Columbia University, for the duration of the fellowship program is fully covered by Hotchkiss. A housing stipend is available during the summer sessions. 

Application Information:

Through the online application process at Hotchkiss.org/careers, interested candidates should submit a cover letter that addresses their interest in teaching at Hotchkiss, with particular focus on their ability and interest in working in an intentionally diverse and inclusive residential community. The cover letter should also address the applicant’s interest in school leadership.

Applicants should also submit their résumé/CV, a statement of teaching philosophy, relevant college and graduate school transcripts, and contact information for three references. The School is committed to building and supporting a diverse community where all feel safe, seen, and supported. Successful applicants will address their ability to contribute to a warm, inclusive, and exciting learning environment. APPLY NOW!

The essential functions and basic skills have been included. It is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities.  Additional functions and requirements may be assigned by supervisors as deemed appropriate.

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 termination).  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.

Department: Associate Head of School/Dean of Faculty

FLSA: Exempt

Reports to: Director, Walter Crain Fellowship Program

Schedule: Academic Year, 9 months in addition to 6 summer weeks when enrolled in KSI

Travel: Occasional

About The Hotchkiss School

Located in the scenic Berkshire-Taconic landscape in the quiet northwest corner of Connecticut, The Hotchkiss School is a community in which faculty and staff members build careers and grow as professionals. We seek to identify, recruit, and develop faculty and staff members who bring a diversity of experiences, perspectives, talents, and backgrounds. Collectively, we are dedicated to supporting the intellectual, social, and emotional growth of 620+ students who come from around the world. In the 2025-2026 school year, our student body includes 17% international students, 41% domestic students of color, and 34% of students receiving financial aid. Geographically diverse, our students represent 35 U.S.states, 32 countries, and span 5 continents. The School is eager to accept applications from individuals who are excited to support an inclusive and warm learning community for students from a wide array of backgrounds and experiences.

Connections working at The Hotchkiss School