Associate Head Of School

Berkshire School | Sheffield, MA, United States

Posted Date 2/15/2024

The Associate Head will work collaboratively with all constituents to enhance the School’s ability to deliver on its mission by nurturing Berkshire’s diverse and inclusive residential community of learners and fostering the academic, artistic, athletic, and personal development of each student. In partnership with the Head of School, and other senior administrators, the Associate Head of School will be a highly visible presence in the school, helping to shape the day-to-day implementation of the School’s philosophy, long-term planning, residential program, and strategic initiatives to advance the School’s mission and achieve operational, strategic, and educational goals.

Please click here for a more detailed job description and responsibilities. You can also view the job description here on Carney Sandoe & Associate's website.

Interested candidates should submit electronically in one email and as separate documents (preferably PDFs) the following materials:

  • A cover letter expressing interest in this particular position
  • A current résumé

As the process moves forward, selected candidates may be asked to submit:

  • Responses to writing prompts specific to this search
  • A list of five professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission)

Candidates are invited to contact the consultants in confidence and to submit a résumé and cover letter as soon as possible to:

Heather Flewelling
Consultant, Chief Talent Officer

Lisa Parsons
Search Consultant

Berkshire offers a substantial and competitive benefits package for full-time employees. Some of the highlights are below:

  • Competitive Compensation
  • Medical/Dental/Vision Health Insurance (Choice of PPO or HSA plans)
  • Retirement Plan through TIAA (5% match first 3-years, 10% after)
  • Student Loan Repayment Assistance
  • Support for Graduate Degree Studies (Faculty)
  • Professional Development Funding (Includes conferences, workshops, travel, etc.)

  • Full Day Student Tuition Remission at Berkshire for all admissible legal dependents
  • Reduced tuition at local independent schools (Indian Mountain School, Berkshire Country Day School)
  • Reduced tuition and priority enrollment at Undermountain Daycare (on-campus)

  • Kellogg Travel Grant (Annually awarded grants to support leisure travel)
  • Strom Grant (Funding available for faculty to travel, study in Asia)
  • Campus Housing
  • Access to Dining Hall
  • Use of athletic facilities and equipment (includes indoor exercise facilities and outdoor track)

Please send employment inquiries to the following unless otherwise noted:


Jean Woodward Maher
Associate Head of School

Berkshire School
245 North Undermountain Road
Sheffield, MA 01257

Fax: 413-229-1010


Cheryl Geerhold
Director of Human Resources

Berkshire School
245 N. Undermountain Road
Sheffield, MA 01257

Phone: 413-229-1201

Employment Type
Full time

Share this job