Staff Positions

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

IT Technician-Level I

Berkshire School is looking for a talented and enthusiastic Level I Technician to offer support in our busy and innovative IT department. The Level 1 Technician provides first line helpdesk support to our students, faculty and staff, including:

  • first line desk-side support for IT related services for students and employees
  • Offering helpdesk ticket triage and escalations, user account management, and printers and printer management
  • Support and troubleshoot system issues related to end-user IT equipment
  • Support and troubleshoot network issues related to desktop/laptops

Successful applicants will have:

  • Working knowledge of Microsoft Operating systems (Windows 7, Window 8), Active Directory,  Microsoft Office suite products and Apple OS X Operating systems
  • Experience working with enterprise Anti-Virus technologies such as Sohos
  • Working knowledge and understanding of network technologies such as TCP/IP, DNS/DHCP, VPN, routers, and switches
  • The ability to provide excellent customer service and work well with both adults and high school students
  • The ability to work independently, manage time and prioritize tasks
  • A desire to learn new technologies

Education and Experience

  • Microsoft certification(s), A+ Certification
  • Minimum of 3 years’ experience 

Interested applicants should submit materials to: Cheryl Geerhold, Director of Human Resources,

IT Technician-Level II

Berkshire School seeks an experienced Level II Technician to join our busy IT department.  The Level II Technician will be responsible for installation, administration, operation, maintenance, and troubleshooting of servers, applications, and related technology systems.  Additionally, the Level II Technician will analyze and recommend evolving technologies that will ensure continuity in the best technical environment.  The Level Two Technician will also provide high level support and assistance to the Help Desk employees and assist Sr. Administrators and Engineers as necessary.

The Level II Technician must have the ability and experience to:

  • Install and maintain server-based applications, upgrades and patches
  • Monitor, troubleshoot, and report on performance of servers and systems
  • Maintain security standards
  • Work closely with the teams to ensure optimal system resources and with the Sr. Admins and Engineers to ensure consistent system support
  • Provide technical support and instruction to front-line computer technicians
  • Assist as needed in maintaining local and wide area network equipment
  • Recognize system deficiencies and implement effective solutions
  • Install and maintain data backups
  • Restore and recover failed systems and data
  • Provide 24/7 support for critical situations and assist with disaster recovery when necessary
  • Analyze and recommend evolving technologies
  • Professionally represent the Infrastructure team as a technical consultant on projects
  • Perform other related work duties as assigned

Successful applicants will be:

  • Able and willing to represent the School in the most positive manner with prospective, former and current students, clients, suppliers and the community we serve.
  • Self-motivated, energetic and creative and possess strong personal computer skills.
  • Able to provide excellent customer service and problem solving skills.
  • Able to work independently, accept responsibility with limited supervision, manage multiple tasks to completion, and work with frequent interruptions.
  • Highly organized and pay  high attention to detail.
  • Able to express oneself clearly and effectively in oral and written form, and able to maintain a very high level of confidentiality.
  • Possessed of excellent human relations skills and have the personality to work in a team environment.
  • Able to demonstrate the highest level of personal and professional integrity.
  • Able to establish and maintain strong working relationships with colleagues and the general public. 

Interested applicants should submit materials to Cheryl Geerhold, Director of Human Resources,


The Major Gifts Officer will report to the Director of Advancement and will identify, cultivate, solicit, and steward donors with the potential to make gifts ranging from $25,000 to more than $1 million and/or deferred gifts.  Significant local, national and international travel is part of this position.  A full job description is available here.

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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