Employment
Berkshire School is a co-ed boarding and day school for students in grades 9-12 and post-graduates, dedicated to serving the best interest of the students and adults living within it. Our 400-acre campus is located at the base of Mount Everett (2,624 ft.) in Sheffield, Massachusetts, in the heart of the Berkshire Hills, a popular tourist destination for world-renowned arts and culture, health and wellness retreats and spectacular nature, including the Appalachian Trail, which is a short hike from campus.
Berkshire instills the highest standards of character and citizenship and a commitment to academic, artistic, and athletic excellence. Our community fosters diversity, a dedication to environmental stewardship, and an enduring love of learning.
CURRENT OPENINGS
Berkshire School strives to create a global community that reflects the world around us and the backgrounds, experiences, identities, genders, perspectives, races, religions and talents that each member brings to our school. We believe that a diverse and inclusive community supports and respects all cultures, ethnicities, languages, philosophies, political views and sexual orientations that exist within and beyond our school.
ADMINISTRATIVE POSITIONS
DEAN OF INCLUSION AND BELONGING
The Dean of Inclusion and Belonging is a member of Berkshire’s senior leadership team, reporting directly to the Associate Head of School, and is responsible for providing strategic leadership to sustain and strengthen the School’s current diversity and inclusion initiatives and to innovate new practices and programs in the areas of diversity, equity, inclusion, and belonging. The Dean plays a central role in engaging with students in Berkshire’s classrooms, afternoon programs, advisories, residential spaces, and throughout the community. The Dean is a strategic partner with school leadership and other campus administrators in the design and implementation of student-centered programs and systems that support Berkshire’s most inclusive community and strongest school culture.
The ideal candidate will have an ability to engage, educate, and inspire others; experience in developing inclusion and belonging initiatives in secondary school settings; and demonstrated success in establishing and fostering meaningful relationships with students and adults.
The Dean of Inclusion and Belonging is a full-time, exempt, full-benefits, 12-month administrative senior leadership position. Salary and benefits are competitive and include year-round, school-provided housing. Professional development funding is available to support advanced degree work as well as participation in professional conferences, workshops, and summer study.
Department: Senior Administrative Leadership
Reports to: Associate Head of School
Roles and Responsibilities
- Serve as a resource, mentor, advocate, and support to students throughout the community to ensure that they are seen, heard, respected, valued, and empowered.
- Serve as a member of the senior leadership team to identify and assess the needs of the student community and to promote the values of equity, inclusion, and belonging.
- Work with Head of School, Associate Head of School, Dean of Faculty, and Director of Human Resources to support inclusion and belonging training and professional development for all adult employees.
- Lead the Inclusion & Belonging Team of adult school leaders from academics, afternoon programs, student life, residential life, admissions, and advancement.
- Work with the Director of Admission and admissions team to recruit and support a diverse student body at Berkshire. Manage, together with the Director of Financial Aid, an annual discretionary budget to support access to a common experience at Berkshire for students receiving financial aid.
- Work with the Dean of Academics and Department Chairs to ensure diversity, equity, inclusion, and cultural competency are central to Berkshire’s pedagogy, classroom practices, curriculum development, and assessment models.
- Work with the Dean of Students, Student Life Office, Student Health Services, and Counseling to ensure that our care of students is inclusive, equitable, and supports healthy identity development and conflict resolution.
- Serve as a resource for students who experience discrimination, marginalization, or bias and ensure appropriate support services are provided.
- Serve as a member of the Hiring Committee and participate in interviews, campus visits, and hiring decisions for all prospective members of the faculty. Assist with identifying and developing new hiring markets, recruitment and retention initiatives, and employment strategies in support of Berkshire’s most talented, diverse, and mission-appropriate employees.
- Participate in the weekly Department Chairs, Form Deans, and Administrative Team meetings.
- Partner with Associate Dean to oversee nine (9) campus affinity groups, including training and support for each group’s student and adult leaders.
- Partner with both the Trustee Committee on Inclusion and Belonging and the full board to provide leadership, perspective, experience, and strategic planning support for the diversity, equity, and inclusion objectives of Berkshire’s 2025 Strategic Plan.
- Partner with Berkshire’s DEI Alumni Council to engage alumni affinity groups and promote alumni mentorship of current students.
- Partner with Associate Dean to oversee nine (9) campus affinity groups, including training and support for each group’s student and adult leaders.
- Develop and oversee ongoing evaluation of the school’s inclusion and belonging initiatives to support future recommendations for integrating these commitments into curriculum, pedagogy, policies, practices, and training.
- Partner and collaborate with local community groups, organizations, and schools.
- Teach one section in an academic department and coach one season/afternoon activity.
Requirements
- Minimum of Bachelor’s Degree; advanced degree preferred.
- Previous experience and familiarity with independent boarding schools is preferred.
Qualifications and Personal Attributes
The strongest candidates are likely to have the following experiences and skills:
- Demonstrated ability and willingness to participate broadly in the life of the school as a teacher, coach/program director, and advisor.
- Demonstrated ability to build, shape, and steward a positive and empowering school culture among both students and adults.
- Demonstrated skill, experience, and sensitivity in working with and within diverse communities and in developing trust and rapport with students.
- Demonstrated ability to communicate with clarity, transparency, timeliness, and empathy to engender trust and confidence throughout our adult community.
- Highly detailed oriented and outcome-based.
- Highest standards of integrity, discretion, and trust.
- Strong interpersonal skills, oral and written communication skills, mediation and conflict resolution skills, and ability to build relationships with diverse stakeholders as part of an effective, collaborative team.
- Creative, organized, self-directed, and capable of effectively coordinating multiple ongoing and one-time tasks simultaneously.
- Knowledge of current best practices and relevant laws regarding diversity, equity, and inclusion work in schools.
- Demonstrated commitment to continued professional development and personal growth in the areas of equity, inclusion, belonging, and school leadership.
Start date: July 14, 2025
DIRECTOR OF HUMAN RESOURCES
Berkshire School seeks an experienced Director of Human Resources for a full-time position beginning July 1, 2025. Berkshire has over 200 adult employees across the faculty, staff, and administration. This is a year-round position with a competitive salary and excellent benefits.
The primary responsibility of the Director of Human Resources is to directly support the recruitment, retention, and development of Berkshire’s strongest adult community. The Director is a strategic partner with school leadership and other campus administrators in the design, assessment, and refinement of programs and policies that support employee excellence at Berkshire. The Director works closely with school leadership and other administrators to support employee orientation, morale, school culture, professional development, recognition, retention, and workplace satisfaction.
Working closely with the CFO and Head of School, the Director monitors and benchmarks benefits and compensation within the industry, working to keep the School competitive and well-regarded to both current and prospective employees. The Director reviews, updates, and presents school policies and programs for all employees, provides guidance regarding applicable regulatory requirements and legal issues pertaining to employees, and also develops, recommends, and evaluates ongoing HR policies, programs, functions, and initiatives that reflect and meet the overall strategic objectives of the School. The Director of Human Resources is a full-time, exempt, full-benefits, 12-month administrative senior leadership position.
Department: Business Office
Reports to: Chief Financial Officer
Roles and Responsibilities
- Work with the Head of School, Associate Head of School, and Dean of Faculty to coordinate professional development and performance evaluations for instructional faculty, administrative faculty, and staff as requested/required.
- With the Head of School, CFO, and Associate Head of School, meet annually to review and recommend all instructional faculty salaries.
- Serve as a member of the Hiring Committee. Identify and develop new hiring markets, recruitment and retention initiatives, and employment strategies in support of Berkshire’s most talented, dedicated, diverse, and mission-appropriate employees.
- Assist and coordinate appointment/reappointment letters and compensation sheets, including the annual review of teaching, coaching, dorm, advising, and other formal responsibilities, for all instructional faculty.
- Participate in the weekly Institutional Leadership Meeting, chaired by the Head of School.
- Serve as a member of and liaison to the Trustee Committee on Human Resources and prepare research, analysis, and reports as requested or needed.
- Coordinate and oversee the School’s annual adherence to the MA Pay Transparency Act.
- Plan, direct, and supervise all activities relating to administration and maintenance of payroll and employee benefits programs. Recommend compensation and benefits offerings that are competitive, non-discriminatory, and equitable across all employees. Make recommendations regarding the development and implementation of programs to ensure cost effectiveness, market effectiveness, and internal salary and benefit equity among employees.
- Administer benefits programs, including conducting analysis and serving as primary contact, along with the Chief Financial Officer, with providers, including group health and life, workers’ compensation, unemployment and retirement plans.
- Serve as a liaison between the School and legal counsel on matters pertaining to employment and policies and advise the administration, trustees, employees, and retirees accordingly. Maintain and expand knowledge and understanding of existing and proposed federal and state laws/regulations affecting human resource management. Identify trends that could affect organizational objectives and/or operational resources.
- Assist supervisors as requested to advertise, recruit, interview, and hire for open positions and communicate with all applicants for those positions.
- Meet with and interview applicants for Staff positions.
- Serve as a member of the Fiduciary Committee.
- Serve as a member of the Risk Management Committee.
- Serve as the School’s primary EEO officer, lead all internal EEO investigations, and prepare and submit annual EEO Report.
- Manage requests for leaves of absence such as sick leave, medical leave, FMLA, MAPFML, and Short Term Disability.
- Provide back-up support for Payroll & Benefits.
- Oversee background checks as required by state and federal law and school policy, store all information as required, track information and conduct periodic audits.
- Arrange for annual training on Sexual Harassment Prevention and maintaining appropriate student/adult boundaries; monitor attendance and participation of all employees.
- Develop, prepare, generate, and analyze ongoing and ad-hoc special reports pertaining to employee personnel information and data.
Requirements
- Minimum of Bachelor’s Degree in a related subject; advanced degree preferred.
- Previous experience and familiarity with independent boarding schools is preferred.
Qualifications and Personal Attributes
The strongest candidates are likely to have the following experiences and skills:
- Demonstrated ability to communicate with clarity, transparency, timeliness, and empathy to engender trust and confidence throughout our adult community.
- Excellent oral and written communication skills in English.
- Highly detailed oriented and outcome-based.
- Highest standards of integrity, discretion, and trust.
- Demonstrated ability to build, shape, and steward a positive and empowering school culture among our adult employees.
- Demonstrated skill, experience, and sensitivity in working with and within diverse communities.
- Business acumen, global and cultural competencies, and commitment to ethical practice.
- Strong interpersonal skills, mediation and conflict resolution skills, and ability to build relationships as part of an effective, collaborative team.
- Previous leadership experience in human resources, employee relations, talent recruitment, and/or talent management.
- Experience with Word, Google, Microsoft Office computer programs, and ADP experience preferred.
- Creative, organized, self-directed, and capable of effectively coordinating multiple ongoing and one-time tasks simultaneously.
- Ability and willingness to work occasional evenings and weekends as job duties demand.
- Willingness to obtain professional development and training as needed and/or requested.
Start date: July 1, 2025
To apply, please contact:
Cheryl Geerhold
Director of Human Resources
cgeerhold@berkshireschool.org
413-229-1201
FACULTY POSITIONS
Our faculty members intentionally choose Berkshire because they recognize we are fully committed to expanding opportunities for our students and furthering their education both inside and outside of the classroom. They are passionate about aligning their work to reflect new understandings of how students learn best and to preparing them for a world driven by exponential change. More than 80% of Berkshire faculty members live in campus housing. Beyond teaching, most faculty members serve as an advisor, coach a sport, help with clubs and activities, and often take on other supervisory roles, which means students interact with faculty multiple times each day in a variety of contexts.
Additional benefits for faculty include year-round housing with utilities, including internet, and meals when school is in session. Funding also exists to support advanced degree work, as well as participation in professional conferences, workshops, summer studies and travel.
HISTORY TEACHER
Berkshire School seeks to hire a dynamic, dedicated, full-time Grade 9-12 History teacher beginning in the 2025-26 school year. The successful candidate will be able to teach the core courses (World History Through Religion, Modern World History, and U.S. History) and demonstrate an ability to develop historical thinking skills, foster engaging discussion, and hone the skills of primary source analysis, analytical writing, and historical application. Candidates should demonstrate understanding and interest in student-centered pedagogy, collaboration, and current historical scholarship. In addition to teaching, applicants should expect to be actively involved in all aspects of the School's programs, including living in a dormitory and participating in the school's athletic and/or co-curricular programs as a coach or program director. A bachelor's degree in History or a closely related field is required and a master's degree or higher is desirable.
VARSITY GIRLS SQUASH COACH
Berkshire School seeks to hire a full-time, dynamic head girls varsity squash coach to begin with the 2025-2026 academic year. The ideal candidate should have a strong record of coaching experience and success, with a demonstrated ability to develop a successful program within the world of New England girls’ squash and to support Berkshire’s broader mission to prepare student-athletes as contributors to their collegiate/university, professional, and personal communities. We are especially interested in candidates who have proven expertise with recruitment, communication, player development, college placement, and who are inclusive in all aspects of their coaching and work with young people. Classroom teachers are preferred, but candidates with experience in other areas of boarding school life are encouraged to apply. The candidate should anticipate being a fully engaged member of our community.
SCHOOL COUNSELOR
Berkshire School seeks a School Counselor to begin during this current school year (2024-25). As a member of the Counseling Department and reporting to the Director of Counseling, this full-time, ten-month position will help support approximately 430 students at Berkshire School. In addition to providing direct support and referrals for students, they will partner with the Director of Counseling in building and sustaining the school’s systems and programs that support well-being and mental health.
Successful candidates for this position will:
- Have five or more years of relevant experience providing counseling and therapeutic support services to adolescents
- Have relevant experience implementing developmentally appropriate, and prevention-oriented social-emotional programs and initiatives, ideally within an independent school setting
- Act as a resource for teachers and administrators, partnering closely with various departments across school life, and broadly assisting the faculty’s efforts to best serve students
- Be open to the opportunity to teach a course on social emotional health
- Co-lead the Peer Listener Program, a leadership group focused on expanding the accessibility of care through a peer-to-peer support model
- Partner with the Director of Counseling in providing consultation and trainings for employees and resources for parents
- Serve on-call in a rotation with other members of the Counseling Office
- Serve as an advisor to a small cohort of students and participate in one season of the Afternoon Program
Qualifications:
- We will consider psychologists, mental health counselors, and clinical social workers.
- Potential candidates should have earned a Master's Degree or PsyD/Ph.D. in psychology, social work, school counseling, or a related field.
- Potential candidates should hold a Massachusetts state license in their field or be license eligible.
- Experience and expertise working with upper school students both individually and in groups is required.
- All clinical theoretical orientations are welcome.
ARTS DEPARTMENT CHAIR
Berkshire School seeks to hire a dynamic, full-time Arts Department Chair (for Visual and Performing Arts) who can teach with-in the visual arts curriculum, beginning in the 2025-26 school year. The individual will oversee the art curriculum and manage department operations. This role involves mentoring fellow teachers, developing engaging art curriculum, and promoting a culture of creativity and artistic exploration among the department and the students. They are expected to have relevant teaching experience with the affection for adolescents, capacity for teamwork, and disposition that such a life demands. In addition to teaching, applicants should expect to be actively involved in all aspects of the School's programs, including living and working in a dormitory and participating in the school's athletic and/or co-curricular programs as a coach or program director. A bachelor's degree in a closely related field is required and a master's degree or higher is preferred.
STAFF POSITIONS
Our staff members are valued members of the Berkshire School community and are vital to the success of achieving our mission. We have numerous staff who have been with Berkshire School for many years, and they cite the warm and supportive community of adults, as well as the enjoyment of working with or around our vibrant, energetic and diverse student body as reasons they enjoy working at Berkshire. In addition to the benefits described above, we have a generous vacation benefit, and all staff are welcome to have meals in our dining hall when they are working.
STAFF NURSE (RN)
Berkshire School has an opening for a Full-Time Staff Nurse in our Student Health Service. Berkshire’s Student Health Service provides medical care to approx. 420 high school boarding and day students. The Staff Nurse is responsible for triage and treatment of students according to written protocols and in collaboration with the Medical Director, athletic trainers, counselors, and Berkshire School staff. Duties are performed during the academic year, and during the summer on a schedule agreed upon with the Director of Student Health Services.
Successful candidates must be kind and able to communicate well with high school students and their families. Requirements: Current MA RN license, CPR/AED certification. Minimum 3 to 5 years of pediatric or school nursing. Knowledge in Electronic Medical Record keeping.
Interested candidates should send resume and cover letter to Brooke Humes, Director of Nursing, bhumes@
GROUNDS/MAINTENANCE
Berkshire School has an opening for an individual to perform routine seasonal outside maintenance and grounds work, and event 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.org, 413-229-1211.
FLIK DINING SERVICES
FLIK Dining Services, which is contracted to provide services for Berkshire School, is looking to hire for the positions listed below. There are both Full-Time and Part-Time opportunities available. Please note, that these are positions with FLIK and not with Berkshire School.
Interested parties should contact Shawn Burdick, Director of Food Services, at 413-229-1216, or sburdick@berkshireschool.org.
LINE SERVER
- Provides quality customer service by providing one-on-one attention to detail.
- Participates in the preparation and service of food and beverage items in adherence to company food standards for presentation, sanitation and safety (meeting HACCP and OSHA guidelines) and portion control.
- Cleans work area and equipment used in food preparation and service.
- Follows all safety and sanitation procedures. Delivers food items to and from main kitchen.
- Promotes clean, safe and neat environment for residents, self and staff.
- Cooperates with staff of other departments in performing job duties.
- Contributes to the team; exhibits professionalism with customers, fellow employees and others.
- Performs other duties as assigned.
DISHWASHER
- Scrapes and rinses food from dirty dishes and washes them by hand or places them in racks or on conveyor to dishwashing machine depending on assigned equipment. Ensures complete cleanliness and sanitation.
- Washes pots, pans and trays based on assigned procedures. Ensure complete cleanliness and sanitation.
- Polishes silver using burnishing machine tumbler, chemical dip, buffing wheel and hand cloth depending on assigned equipment and procedures. Ensures complete cleanliness and sanitation.
- Ensures compliance with outlined safety procedures.
- Maintains temperatures and chemical levels as outlined by provided standards.
- Keeps dish area orderly and in compliance with safety standards.
- Sweeps and mops kitchen floors to ensure compliance with safety and sanitation standards.
- Washes worktables, walls, refrigerators, meat blocks and other food prep surfaces.
- Removes trash and places it in designated containers. Steam cleans or hoses out garbage cans.
- Transfers supplies and equipment between storage and work areas.
- Helps load and unload supplies and product.
COOK
Learns to assists in the preparation and cooking of various food items prior to being considered a qualified, skilled cook. Maintains food safety and sanitation standards in the preparation and kitchen areas.
- Learns to read menu to estimate food requirements. Orders food from supplier or procures it from storage.
- Prepares and cooks food in accordance with company production records and standardized recipes.
- Learns to adjust thermostat controls to regulate temperature of ovens, broilers, grills, roasters and steam kettles.
- Helps measure and mix ingredients according to recipes using a variety of kitchen utensils and equipment.
- Bakes, roasts, broils and steam meats, fish, vegetables and other foods under guidance. Adds seasoning to food during mixing or cooking under the instruction of others.
- Tests food by tasting, smelling and piercing to determine that it is cooked.
- Carves meat, portions food on serving plates, and adds gravies, sauces and garnishes to fill orders as directed.
- Washes, peels, cuts and shreds fruits and vegetables and fruits.
- Butchers chicken, fish and shellfish as directed.
- Bakes bread, rolls, cakes and pastry as course of instruction permits.
- Maintains work station
BENEFITS
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)
CONTACT
Please send employment inquiries to the following unless otherwise noted:
FACULTY POSITIONS
To apply for a faculty position at Berkshire, please send a cover letter of interest and resume to teaching@berkshireschool.org
STAFF POSITIONS
To apply for a staff position at Berkshire, please send a cover letter of interest and resume to Cheryl Geerhold,
director of Human Resources.
Email: cgeerhold@berkshireschool.org
Phone: 413-229-1201
Berkshire School
245 N. Undermountain Road
Sheffield, MA 01257
AT-A-GLANCE
425
STUDENTS
39
COUNTRIES
30
STATES
12
AVERAGE
CLASS SIZE
33
ADVANCED
COURSES
$195M
ENDOWMENT
100%
GRADUATES ATTEND COLLEGE