Staff Positions

Berkshire School is an equal opportunity employer

Administrative Assistant-Student Life Office

Berkshire School has an opening for a full-time position as the Administrative Assistant in the Student Life Office. The administrative assistant in the Student Life Office assists the Dean of Students and Assistant Dean of Students in the following ways: compiling and distributing information to students and their families regarding policies in the Student Life Office. Collecting information over the summer and at opening of school registration. Creating and distributing student id cards and room keys, maintaining student travel records for weekend and vacation travel, managing a data base for attendance purposes at a variety of events, and other tasks as directed by the Dean of Students.

This position requires outstanding administrative, clerical and organizational skills, the ability to work well with both high school students and their parents, excellent computer, word processing, and communication skills, and the ability to maintain a welcoming atmosphere in the office. This position is a full-time, hourly position when school is in session, with reduced hours when school is not in session. At specified times during the year, holiday or Sunday hours are required.

Successful candidates will have experience working as an Administrative or Executive Assistant with the knowledge and experience to handle multiple priorities, visitors and callers in a professional, polished manner.           

Please mail letter of interest and resume to Cheryl Geerhold, Director of Human Resources, Berkshire School, 245 N. Undermountain Road, Sheffield, MA 01257, or e-mail

Berkshire School is an equal opportunity employer.

Substitute Teacher

Undermountain Child Care Center at Berkshire School is looking for a substitute teacher who is available for flexible coverage.  Applicants with some Early Childhood teaching experience are preferred.  A CORI check and SAFIS check are both required.  Interested applicants please email or send resume and letter of interest to Director, Tammy Wysocki,, or 245 N Undermountain Rd, Sheffield, MA 01257

Grounds/Maintenance Position 

Berkshire School has an opening for an individual to perform routine seasonal outside maintenance and grounds work, and even set-ups and breakdowns.  This position requires heavy lifting and the ability to work as an effective member of a team.  Some weekend and holiday hours are mandatory. This is a full-time, year round position with excellent benefits. Interested parties should contact Gabe Starczewski, gstarczewski@berkshireschool.org413-229-1211.

Director of Donor Relations

Berkshire School’s Advancement Office is seeking a Director of Donor Relations to provide strategic thinking, leadership, and management of Advancement-related communications.  Successful applicants will have a minimum of a Bachelor’s degree; minimum 3 years of Advancement communications, donor relations or related Advancement services; exceptional communications and strategic thinking capabilities, and a clear understanding of independent school culture.  A full job-description is available here.

The position is full-time and includes generous benefits.

Interested parties may submit resume, cover letter and three (3) writing samples to Cheryl Geerhold, Director of Human Resources,

Berkshire School is an Equal Opportunity Employer

Interested candidates should contact Cheryl Geerhold, Director of Human Resources,

Berkshire School

245 North Undermountain Road
 |  Sheffield, MA 01257
 |  T: 413 229 8511

Berkshire School is a co-ed, New England college preparatory boarding and day school offering a rigorous academic course of study in the northeast United States. Our campus, located in Massachusetts, has state-of-the-art academic, artistic and athletic facilities on a stunning 400-acre campus in the Berkshires.

Berkshire School received 5 out of 5 stars from over 3 Google reviews.
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