General Applications

Please send a letter of interest, a resume, and a list of three references to:

Kristin Welage
Director of Human Resources
Cheshire Academy
10 Main Street
Cheshire, CT 06410

An e-mailed pdf of these documents is preferred.

Cheshire Academy is an equal opportunity employer. Salary and benefits are competitive. 

Administrative Openings

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  • Director of Admission

    12-month Administrative appointment
    FUNCTION: The Director of Admission reports to the Head of School and will be a member of the senior leadership team of Cheshire Academy. In this capacity, she/he will not only be charged with overall responsibility for recruitment, admissions, enrollment management, and financial aid, but will also contribute at a senior level to the broad strategy and goals of Cheshire Academy. The Director leads a staff and collaborates closely with academic and administrative leaders across the campus.
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Faculty Openings

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Staff Openings

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  • Data and Research Specialist

    12-month appointment

    FUNCTION: Reporting to the Chief Advancement Officer, the Data and Research Specialist has responsibility for maintaining the full constituency data-base and employing creative strategies to maintain current biographical and demographic data to support outreach and engagement of Cheshire Academy’s alumni, parents and friends. The specialist will enter gifts and pledges and receipt as appropriate, produce gift acknowledgements, and maintain other customer relationship management systems. The successful candidate will ensure a level of database integrity that supports use to its fullest capacity for prospect identification, cultivation, solicitation, and stewardship, as well as active research through on-line and other sources to support prospect development and performance analytics.

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Internship Openings

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.


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSION OFFICE: 203-439-7250
ADMISSION FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

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  • The Student-Centered Private School in Connecticut.

    We put the unique needs of every student first. That’s why we offer a flexible program that allows students to mix academic course tracks with athletics and/or fine arts programs, according to their needs and interests.
    Students can stretch their intellectual boundaries by taking one of 20 advanced International Baccalaureate® Diploma Programme courses, or practice new skills by participating in a range of afternoon programs including; athletics, fine arts, and performing arts. We are also the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program.
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