Teaching at Cheshire Academy

Faculty members participate in a full boarding school program, with academics, arts, and athletics. Community is an important part of the Cheshire Academy experience and we strive to live by our 8 Pillars of Bowden: Respect, Responsibility, Caring, Civility, Citizenship, Morality, Fairness, and Trustworthiness.

In addition to teaching, other responsibilities include: advising, coaching and/or leading extra-curricular activities, and weekend team responsibilities.

Nondiscrimination Policy

Cheshire Academy, as an equal opportunity employer, complies with all applicable federal and state laws regarding nondiscrimination.  Cheshire Academy is committed to a policy of equal opportunity for all persons and does not discriminate on the basis of race, color, national origin, age, marital status, sex, sexual orientation, gender identity, gender expression, disability, religion, height, weight, or veteran status in employment, educational programs and activities, and admissions.

Teaching Faculty




The men and women who make up the teaching faculty teach in small classes and exercise great authority in academic and disciplinary matters. The academic program at Cheshire Academy is guided by the principles of student centered learning, in a constructivist instructional model. Within the range of students preparing for admission to four-year colleges and universities, teachers often differentiate their instruction to accommodate differences in learning modalities and styles. This approach encourages students to take responsibility for their own learning and to actively participate in the construction of their knowledge.

The typical course load is four classes that meet four times per week in 45-minute periods (more with labs or intensive courses). The standard teacher load is 50 students, with an average of 12 students per class. As members of a residential community, Academy teachers work to realize excellence not only in classroom teaching but also in their dormitory work, their advising of students, their coaching, and their wider involvement as a constructive force in the lives of students.

Ordinarily a faculty member coaches or supervises an activity in the afternoon program two out of three seasons. Some assignments are in the interscholastic program where teams practice four times a week and compete on Wednesday and Saturday afternoons. Other assignments are the intramural programs that meet four days a week.
Each faculty member is an advisor to seven or eight students, serving as the communications link between the student, teachers and family. Advisors meet briefly each day with advisees but often arrange longer sessions each week to discuss their academic progress, extracurricular activities and any other concerns that arise during the year. Professional counselors are available as a resource as well.
Student Activities
Faculty members sometimes take on responsibility for advising clubs, school publications, community service activities, and other programs that enhance the educational experience of the students. A faculty member volunteers or is asked to serve as an advisor to a student activity according to interests and workload.
Committee Work
A faculty member is appointed or elected to committees, standing and ad hoc. Committee work is distributed as evenly as possible among faculty members and according to individual interests, if possible.
Faculty who live in dormitory apartments or other school housing help to supervise the boarding students on weeknights and weekends as resident faculty members or affiliates. In a dorm, faculty and proctors work together as a team to make the residential experience one in which students can learn from one another. Dormitory duty usually involves one to two weekday nights of regular duty, one or two nights of backup duty, and weekend duty every three or four weekends, depending on the number of faculty members working in the dormitory. All Upper School faculty, whether living in a dormitory or not, are assigned to a Duty Team to do weeknight duties and help chaperone weekend activities.

Candidates who wish to apply for a teaching position should have the following qualifications:

  • Bachelor’s degree in the discipline you wish to teach; advanced degrees encouraged (State certification is not required.)
  • Ability to coach one or more sport and/or advise an extracurricular activity
  • Ability to obtain as CT driver’s license with Class A endorsement to transport students
  • A genuine interest in working with adolescents
  • Good communication skills, both oral and written
  • Commitment to professional growth

It is expected that all teachers at Cheshire Academy will have a proven mastery of the subject matter for the teaching position being sought. As such it is expected that teaching faculty will have teaching experience in their specific discipline.



Salaries: In line with salaries for new teachers with advanced degrees at Cheshire Academy. Teachers are given salary credit for teaching experience.

Benefits: Academy Tuition Remission, Health Insurance, Dental Plan, Worker’s Compensation, Long-term Disability, Short-term Disability, Group Life Insurance, Retirement Plan, Faculty Housing, Dining Hall Privileges.

Professional Development: Summer grants for coursework and research; Cheshire Academy Summer School and summer sports clinics; possible foreign study tours; conference attendance; graduate-course subsidies are available to faculty.


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Address: 890 Lorem Ipsum Street #12 San Francisco, California 65432 Phone: 123.4567.890 Business Hours: 8a-6:30p M-F, 9a-2p S-S