Berkshire School is a boarding community dedicated to serving the best interest of the students and adults living within it. We hire proven leaders who recognize the benefit of hard work, building community and sharing success. While most full-time faculty will teach four sections, coach two seasons and work within the residential program, every successful employee working at the School understands and appreciates the twenty-four hour nature of a Berkshire education, which is why working at Berkshire is a way of life and not simply a job.

Berkshire School is an equal opportunity employer.

Faculty Positions

Send inquiries to:

Jean Woodward Maher
Associate Head of School
Berkshire School
245 North Undermountain Road
Sheffield, MA 01257

email jmaher@berkshireschool.org
fax 413-229-1010

Staff Positions

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, umcc@berkshireschool.org, or 245 N Undermountain Rd., Sheffield, MA 01257

Technology Associate

This position serves the entire school community. The primary responsibility is to support students, faculty and staff in all areas of technology. The Technology Associate reports to the Director of Technology but will also take direction from the Network Administrator and Information/Education Technology Administrator.

Position Type: Non-exempt

Reports to: Director of Technology

Schedule: 12 month


The Technology Associate’s responsibilities include, but are not limited to:

●Support of the IT Help Desk; monitoring, managing, documenting and tracking of all issues and solutions.

●Diagnosis and troubleshooting of problems with computer systems, including hardware and software, email, network and peripheral equipment.

●Perform maintenance and repair of PC based computer, Apple computers, iPads, and all other peripheral devices.

●Maintain accurate inventory of school wide equipment along with IT team members.

●Imaging and installation of software and system upgrades on new and existing computers.

●Support of Google Apps for Education environment, cloud/web based technology, and other services and associated end user management.

●Provide assistance to System Administrators with maintenance and upkeep of infrastructure.

●Construct and organize professional development training for students, faculty and staff as needed.

●Research and provide solutions for obsolete or discontinued software.

●Provide audio/video support as needed for campu spaces and classrooms.

●Troubleshoot issues related to all classroom technology resources.

●Other duties as required.


●Strong interpersonal skills with a customer service focus.

●Proactive, solutions based mindset.

●Ability to work in a team environment.

●Strong organizational skills, the ability to meet deadlines and think independently.

●Ability to work with adults and students of various competency levels.

●Motivation to learn through professional development and certification training.


●High School diploma with two plus years of college and/or computer education.

●One plus year(s) experience as an IT Help Desk professional.

●Experience troubleshooting issues with Windows computers, Mac computers, laptops and mobile devices.

●Experience with Wifi platforms and access point deployments.

●Basic understanding of network topology, configuration, protocols and how to troubleshoot in this environment.

●Microsoft certification/A+ certification a plus with proficiency in Windows 10.

●Network+ and Security+ certification a plus.

●Basic understanding of Active Directory and DNS.

●Must be able to lift 60 pounds independently.

●Able to work with multiple distractions and changing priorities.

●Able to work during off peak and extended hours.

●Must enjoy working with adults and students who approach the use of computers and technology from an educational point of view.

Interested and qualified candidates should email the below materials to Director of Human Resources Cheryl Geerhold at cgeerhold@berkshireschool.org.

Assistant Director of Communications and Marketing

The Assistant Director of Communications and Marketing is a 12-month, full-time position within the Communications and Marketing Department. The Assistant Director’s main responsibility will be to report on campus life and alumni news for social media, website, and the electronic newsletters. The person in this role will be responsible for creating messaging that supports Berkshire School’s institutional priorities and developing communications that directly support the School’s mission.

Job Functions/Major Responsibilities

•Manages the School’s official social media channels including: Facebook, Twitter, Instagram, Snapchat, and YouTube

•Leads the daily planning and execution of all social media content and strategies

•Identifies compelling story ideas and creates digital content that is informative, impactful, and celebrates the School’s success stories

•Participates in campus events and activities to post live streams, photography, quotes, and other content

•Reports real-time athletics scores for the School’s athletics Twitter account

•Develops and maintains social media metrics to guide decision-making, increase engagement, and to test new approaches

•Manages and maintain the athletics pages on the website (overview, team rosters, coach information, and team photos)

•Conceives and writes timely athletic news features for the website (athletic awards, playoff games, student profiles, New England titles /records, recruitment, alumni achievements, etc.)

•Coordinates with the Assistant Director of Athletics to schedule and execute team photos for all teams.

•Works with the Advancement Office to maintain a list of notable alumni athletes as well as current alumni athletic achievements

•Coordinates and executes photo shoots, including academic, artistic, athletic events and other areas of campus to support marketing efforts

•Maintains and manages the photography database (Resource Space)

•Helps proofread print and online communications and publications

•Collaborates with the Associate Director of Communications and Marketing on video projects.

•Coordinates the end-of-year senior video with students for Prize Night

•Assists with administrative duties (budgeting, advertising, etc.)


•Candidate must possess a Bachelor’s Degree

•High proficiency in all social media applications, including Facebook, Twitter, Instagram, etc. and awareness of new developments in social media

•Organization and the ability to address multiple issues simultaneously in a busy office atmosphere

•Excellent interpersonal skills and ability to work effectively with students and adults

•Strong communication skills, both verbal and written

•Excellent computer skills, fluent in Microsoft Office and knowledge of current desktop publishing software, preferably Photoshop, Adobe InDesign or Illustrator

•Must be available on some evenings and weekends

•Photography skills is a plus

This is a staff position; no campus housing

Interested and qualified candidates should email the below materials to Director of Human Resources Cheryl Geerhold at cgeerhold@berkshireschool.org.

Administrative Positions

There are currently no positions available.