Careers
Thank you for your interest in Berkshire School—a vibrant and welcoming community set at the foot of Mount Everett in Sheffield, Massachusetts. Working at Berkshire means being part of something truly special: a school deeply committed to academic, artistic, and athletic excellence, where students are curious, creative, and kind. It’s a place where educators and staff are inspired daily by the natural beauty surrounding campus and the shared mission to shape thoughtful, well-rounded young people.
Potential Openings for the 2026-2027 Academic Year
We’ll know more about our specific openings soon, but in the meantime, here are the areas where we anticipate having opportunities for the 2026–2027 school year:

Teaching
English Department
History Department
Math Department
Science Department

Coaching
We anticipate potential openings at both the varsity and sub-varsity levels in the following sports:
Basketball
Hockey
Soccer
Squash
Tennis

At Berkshire, our educators are curious, collaborative, and deeply committed to fostering meaningful relationships with students both inside and outside the classroom. A Berkshire educator is a lifelong learner who values community, brings enthusiasm and expertise to their work, and embraces the opportunity to engage fully in all aspects of school life.
Most full-time faculty at Berkshire teach four classes or an equivalent (i.e. Assistant or Associate Director of Admission or Athletics), serve as an advisor, support the athletics/afternoon program across two seasons, and play an active role in the residential life program.
If any of these potential opportunities resonate with you, or if you’d simply like to learn more about what it means to be part of the Berkshire community, we’d love to hear from you. Please reach out to teaching@berkshireschool.org for more information.
Current Openings
FACULTY
History Teacher
Berkshire School seeks a dynamic, intellectually curious, and student-centered History teacher for the 2026–2027 academic year. This role is ideal for an educator who believes deeply in the study of history as a means of developing critical thinking, empathy, and a nuanced understanding of the modern world—and who is excited to teach and mentor adolescents in a highly relational boarding school environment.
At Berkshire, history teachers do far more than deliver content. They foster lively, inquiry-driven discussion, challenge students to engage deeply with primary sources, and help students develop the analytical and writing skills necessary to think historically and responsibly. The ideal candidate will bring both strong content knowledge and a genuine enthusiasm for guiding students as thoughtful interpreters of the past.
A successful candidate is someone who:
- Engages students through discussion-based, student-centered pedagogy.
- Helps students develop historical thinking skills, including source analysis, contextualization, and argumentation.
- Encourages curiosity, intellectual risk-taking, and respectful dialogue.
- Communicates with clarity, warmth, and purpose—both in and beyond the classroom.
- Thrives in collaboration and values shared curriculum design and reflection.
- Demonstrates interest in current historical scholarship and evolving pedagogical practice.
- Supports and challenges students across varied learning styles, identities, and backgrounds.
- Sees teaching as part of a larger commitment to student life and community engagement.
Teaching Responsibilities
- Teach a range of history courses in grades 9–12, including core offerings such as World History Through Religion, Modern World History, and United States History.
- Design lessons that emphasize close reading of primary and secondary sources, analytical writing, and historical application
- Assess student learning thoughtfully and provide timely, constructive feedback.
- Participate fully in departmental collaboration, curriculum development, and ongoing professional growth.
Community Engagement
Full-time members of the faculty are deeply engaged in the life of the School and contribute to Berkshire’s academic, afternoon, and residential programs. Responsibilities include:
- Serving as a student advisor.
- Participating in two seasons of afternoon athletics or co-curricular programming (as a coach or program director).
- Living in a dormitory or serving as an adjunct residential faculty member.
- Contributing to committee work and broader school initiatives.
Qualifications
- Preferred: Secondary-level teaching experience; Master’s degree or higher.
- Required: Bachelor’s degree in History or a closely related field.
To apply, please email your résumé and cover letter to teaching@berkshireschool.org and addressed to Allison Letourneau, Associate Head of School
Posted: January 26, 2026
Salary Range: $50,000 USD to $100,000 USD
Spanish Teacher
Berkshire School seeks a dynamic, intellectually curious, and student-centered Spanish teacher for the 2026–2027 academic year. This role is ideal for an educator who believes deeply in the study of language as a means of building cultural understanding, communication, and global perspective—and who is excited to teach and mentor adolescents in a highly relational boarding school environment.
At Berkshire, language teachers do far more than teach grammar and vocabulary. They cultivate immersive classroom environments where students actively engage in Spanish through conversation, authentic texts, and cultural exploration. The ideal candidate will bring strong linguistic proficiency, a passion for Hispanic cultures, and a commitment to helping students develop confidence and fluency in speaking, listening, reading, and writing.
A successful candidate is someone who:
- Engages students through communicative, student-centered language instruction.
- Creates immersive classroom experiences that prioritize meaningful conversation in Spanish.
- Incorporates authentic cultural materials—literature, film, media, and current events—to deepen cultural understanding.
- Encourages curiosity, risk-taking, and confidence in language acquisition.
- Supports students as they develop proficiency across all modes of communication: speaking, listening, reading, and writing.
- Communicates with clarity, warmth, and purpose—both in and beyond the classroom.
- Thrives in collaboration and values shared curriculum development with colleagues.
- Supports and challenges students across varied learning styles, identities, and backgrounds.
- Sees teaching as part of a larger commitment to student life and community engagement
Teaching Responsibilities
- Teach a range of Spanish courses in grades 9–12, from introductory through advanced levels.
- Design lessons that emphasize conversation, cultural understanding, and authentic language use.
- Assess student learning thoughtfully and provide timely, constructive feedback.
- Participate fully in departmental collaboration, curriculum development, and ongoing professional growth.
Community Engagement
Full-time members of the faculty are deeply engaged in the life of the School and contribute to Berkshire’s academic, athletic, and residential programs. Responsibilities include:
- Serving as a student advisor.
- Participating in two seasons of afternoon athletics.
- Living in a dormitory or serving as an adjunct residential faculty member.
- Contributing to committee work and broader school initiatives.
Qualifications
- Preferred: Secondary-level teaching experience; Master’s degree or higher in Spanish, Hispanic Studies, or a related field.
- Required: Bachelor’s degree in Spanish or a closely related field and advanced proficiency in Spanish.
To apply, please email your résumé and cover letter to teaching@berkshireschool.org and addressed to Allison Letourneau, Associate Head of School
Posted: March 19, 2026
Salary Range: $50,000 - $100,000
Technical Director
Berkshire School seeks a collaborative, creative, and highly organized Technical Director to support the School’s performing arts programs beginning in the 2026–2027 academic year. This role partners closely with the Theater, Dance, and Music programs to design and execute the technical elements of performances while also serving as a mentor and instructor to students interested in technical theater.
At Berkshire, the performing arts are an important part of the student experience. The Technical Director plays a central role in bringing productions to life—working with faculty directors and student crews to design and build sets, manage lighting and technical elements, and ensure that performances are safe, professional, and artistically compelling.
The ideal candidate is both a skilled technician and an educator who enjoys teaching students practical theater skills and helping them understand the creative and technical process behind live performance.
A successful candidate is someone who:
- Collaborates creatively with faculty directors to design and execute scenic, lighting, and technical elements for productions.
- Oversees the construction and installation of sets and stage elements.
- Teaches and supervises students in technical theater practices, including shop safety and theatrical construction techniques.
- Maintains theater equipment, lighting systems, and production spaces.
- Supports lighting design and technical needs across theater, dance, and music performances.
- Demonstrates initiative and curiosity in learning new technical skills as production needs evolve.
- Communicates clearly and works collaboratively with faculty, students, and production teams.
- Values safety and ensures appropriate protocols are followed in all shop and stage environments.
- Sees technical theater as both a creative discipline and an educational opportunity for students.
The Technical director will:
- Design and build scenic elements for theatrical productions.
- Oversee the acquisition, construction, and documentation of props for productions.
- Collaborate with performing arts faculty to support lighting, staging, and production design for concerts, dance performances, and theater productions.
- Manage the theater shop, including tools, equipment, and materials.
- Supervise student crews during builds, rehearsals, and performances.
- Maintain lighting plots, equipment inventories, and production documentation.
- Support technical rehearsals and performances throughout the academic year.
Community Engagement
● Teach two academic sections.
Physical Requirements
This role requires the ability to perform a range of physical tasks in support of theater productions and technical operations. The employee must be able to stand and move for extended periods; lift, carry, and position materials and equipment (typically up to 50 pounds, occasionally more with assistance); and perform activities such as bending, kneeling, crouching, climbing, and reaching overhead.
The position involves working with hand and power tools, stage equipment, ladders, and lifts, including work at heights (e.g., catwalks or personnel lifts). The employee must be comfortable working in theater and shop environments with exposure to dust, noise, and varying temperatures.
The role also requires the stamina and focus to support rehearsals, builds, and performances, including evenings and weekends, and the ability to consistently follow and enforce safety protocols in shop and stage settings.
Qualifications
Preferred: Professional experience in technical theater production or a BFA/MFA in technical theater, theater production, or a related field.
Experience working with or teaching students in a theater or educational setting.
Posted: March 30, 2026
To apply, please email your résumé, cover letter, and digital examples of prior work to teaching@berkshireschool.org and addressed to Allison Letourneau, Associate Head of School
Salary Range: $50,000 - $100,000
ADMINISTRATIVE
Associate Dean of Inclusion and Belonging
The Associate Dean of Inclusion and Belonging plays a key leadership role in sustaining and strengthening a culture of belonging at Berkshire School under the Mountain. The role is primarily student-facing and relational, with an emphasis on building trust, fostering connection, and serving as a consistent liaison among student groups, affinity spaces, and the broader campus community. Through presence, listening, and guidance, the Associate Dean helps ensure that inclusive practices and shared values are lived daily across student life.
This is a highly relational role for an educator-administrator who thrives at the intersection of student leadership, community engagement, and institutional values.
What You’ll Bring to the Role
The Associate Dean of Inclusion and Belonging is someone who:
- Believes belonging and dignity are foundational to learning and character development
- Builds strong, trusting relationships with students across identities and experiences
- Is energized by student leadership, dialogue, and community-building
- Brings organization and follow-through to complex, student-centered initiatives
- Communicates with clarity, empathy, and professionalism
- Understands inclusion and belonging as shared responsibilities across campus life
Key Responsibilities
- Partner with the Dean of Inclusion and Belonging in advancing Berkshire’s vision for
- inclusion, belonging and dignity.
- Serve as a primary liaison to student affinity groups, providing mentorship, guidance, training, and support to both student and adult leaders.
- Serve as an active member of the Belonging Collective, contributing to planning, reflection, and action related to campus culture and community life.
- Support and help coordinate major campus-wide programs and commemorations, including but not limited to MLK Day, International Holocaust Remembrance Day, Black History Month, Lunar New Year, and other identity- and community-centered celebrations.
- Advise and support student leaders as they plan and implement events, dialogues, and initiatives that foster belonging and cross-community engagement.
- Collaborate with Student Life, Residential Life, Athletics, Academics, Admissions, and Advancement to ensure inclusive practices are integrated across the student experience.
- Serve as a resource and advocate for students navigating identity-related questions, challenges, or moments of transition.
- Serve as a connector between student experience and institutional leadership by surfacing themes, concerns, and insights that inform inclusive decision-making
- Assist in the development and implementation of training, workshops, and educational programming related to inclusion and belonging.
- Collaborate with faculty and campus partners to support student-centered learning opportunities related to inclusion, belonging, and community life.
- Support assessment and reflection efforts to help evaluate the impact of inclusion and belonging initiatives and inform future planning.
Community Engagement
As a full-time member of the faculty, the Associate Dean of Inclusion and Belonging is an active participant in campus life and contributes to Berkshire’s academic, afternoon, and residential programs.
- Teach 2 sections.
- Serve on a dorm or duty team.
- Participate in afternoon programming for 2 seasons.
Posted: March 6, 2026
This role offers meaningful opportunities for professional growth and leadership development, with flexibility to align responsibilities with both institutional needs and the strengths of the successful candidate. To apply, please email your résumé and cover letter to Allison Letourneau, Associate Head of School (aletourneau@berkshireschool.org). Review of applications will begin immediately and continue until the position is filled.
Salary Range: $50,000 USD to $100,000 USD
STAFF
Nurse
We are seeking part-time and per diem Nurses responsible for triage and treatment of students according to written protocols and in collaboration with the Medical Director, Director of Nursing, athletic trainers, counselors, and Berkshire School staff.
Job Functions/Major Responsibilities:
Clinical Care and Triage:
- Provide nursing level care for student illness or injury.
- Determine nursing diagnosis and develop a plan of care using established protocols.
- Perform laboratory tests as needed.
- Handle medical emergencies campus-wide.
Medication Administration and Documentation:
- Administer prescription medications or vaccinations per physician order.
- Administer over-the-counter medications with parent/guardian permission per SHS protocol.
- Keep accurate records; document and maintain electronic health records neatly and legibly.
Student Support and Education:
- Provide health education and information as needed.
- Refer students to the Medical Director or school counselor as appropriate.
Infirmary and Program Support:
- Monitor inpatients closely.
- Make up inpatient beds.
- Provide meals.
- Perform other necessary tasks in Student Health Services, including inventory and ordering supplies.
- Participate in SHS office meetings.
- Engage in continuous professional development.
Communication and Coordination:
- Communicate with medical and non-medical personnel at school and with student families regarding a student’s condition, as appropriate.
- Communicate student absences and appointments to the Administrative Assistant and enter excused absences in the computer system.
Coverage and Transportation:
- Participate in the rotation for nights and weekends (virtual and in person) per SHS schedule.
- Occasionally transport students via a school vehicle on and off campus.
Knowledge/Skills/Competencies:
- Current Massachusetts Nurse Licensure.
- Graduation from an ACEN or CCNE accredited nursing school.
- Current CPR Certification.
- Minimum 1 year experience in a school or hospital or the equivalent.
- Ability to provide physical examination, nursing diagnosis and treatment for students.
- Ability to administer immunizations.
- Excellent written and verbal communication skills.
- Strong organizational skills and ability to prioritize.
- Ability to work both independently and as part of a team.
Other Duties:
This job description is not designed to cover or contain a comprehensive listing of all activities, duties or responsibilities that are required. Duties, responsibilities, and activities may change, or new ones may be assigned at any time.
Physical Requirements:
Ability to lift up to 50 pounds, with or without reasonable accommodation.
- Ability to sit, stand, and move throughout the workday.
- Ability to use a computer and other equipment for documentation and recordkeeping.
- Ability to communicate effectively and respond promptly to student health needs, including emergencies.
Other:
- Employment is contingent upon the successful completion of CORI/SORI and other background checks as required by Berkshire School and applicable law.
- Clean driving record (for student transport needs).
Posted: January 23, 2026
Please send a cover letter of interest and resume to Etienne Marofsky,
Director of Human Resources
emarofsky@berkshireschool.org
Salary Range: $35–$50 per hour (Academic year, some scheduled summer hours)
Associate Director of Content
We are seeking a highly creative, experienced, and results-driven Associate Director of Content. This role is central to developing and executing a communication strategy that authentically messages the Berkshire School experience and reinforces the school’s mission by creating digital, print, and social media content that connects external audiences to life "under the Mountain," supports the Office of Admission in recruiting prospective families, and amplifies the Advancement Office's fundraising and alumni engagement initiatives. The ideal candidate will be a strong storyteller, a meticulous editor, and an innovative contributor to our social media strategy and execution.
Job Functions/Major Responsibilities:
Written Content Creation:
- Lead the identification, creation, and distribution of compelling stories that authentically reflect the Berkshire School experience, focusing on student success, faculty and academic excellence, campus life, and the institutional mission.
- Partner with the Director of Communications and Marketing to write, edit, and produce high-quality short-form and long-form communication materials, including the alumni and parent magazine (1-2x a year), monthly digital newsletters, website content, press releases, and more.
- Report on campus life, student experience, and events.
Social Media:
- Collaborate with the entire Communications and Marketing team on social media idea generation.
- Monitor social channels for unique or trending topics and opportunities to highlight Berkshire's unique story, experience, and offering.
- Create and maintain a detailed, proactive social media content calendar that holistically highlights campus life, academic excellence, Admission and Advancement initiatives, and events at Berkshire.
- Support Director of Communications and Marketing on the development of social media copy and execution of posts.
Brand Voice and Editing:
- Act as a guardian of the school’s voice, ensuring all written communications are consistent, grammatically correct, engaging, and aligned with the school’s mission and branding.
- Help proofread communications and publications developed by the Communications and Marketing Department and by other departments of the school, as needed.
Photography:
- Capture campus events, including during some evenings and weekends, in support of social media and storytelling across different media platforms.
Print Production Support:
- Partner with the Director of Communications and Marketing and outside vendors on the development, production, and distribution of all print school publications including, but not limited to, the alumni and parent magazine, Admission materials, newsletters, and other marketing materials.
Other
- Support needs of Communications and Marketing Department and the larger Berkshire School community as needed with ad-hoc requests and projects.
- Collaborate with other departments and team members on various projects.
Knowledge/Skills/Competencies:
- B.A. degree required; a minimum of 5-7 years related experience in communications, marketing or public relations.
- Excellent written and oral communication skills; exceptional editing skills essential.
- Experience in all social media platforms, particularly Instagram.
- Familiarity with independent school culture or work within an educational setting is preferred.
- Position requires the ability to manage several multifaceted projects simultaneously, attention to detail, and a demonstrated ability to multi-task and meet aggressive deadlines.
- Exceptional interpersonal skills and ability to work effectively with students and adults and ability to build relationships with faculty, staff, and students.
- Ideal candidate will be an analytical and creative thinker and a persuasive writer, capable of synthesizing data into prose.
- A willingness to photograph and film campus events, some during the evenings and on weekends, is essential. Photography and video production and editing skills are a plus.
- Position requires some evening and weekend commitments to capture and report on school events. 2-3x a month, on average throughout the school year.
- Excellent computer skills, fluent in Google Workspace and preferably Photoshop, Canva, and Adobe.
Physical Requirements:
- Ability to perform the physical requirements of the position, including moving about campus and lifting equipment up to approximately 25 pounds, with or without reasonable accommodation.
Other:
- Employment is contingent upon the successful completion of CORI/SORI and other background checks as required by Berkshire School and applicable law.
- Clean driving record.
Please send a cover letter of interest and resume to Etienne Marofsky,
Director of Human Resources
emarofsky@berkshireschool.org
Posted: January 19, 2026
Salary Range: $55,000 USD to $65,000 USD
FLIK DINING SERVICES
UNDERMOUNTAIN CHILDCARE CENTER
Early Childhood Teacher
We are seeking an Early Childhood Toddler Teacher to support a nurturing, safe, and developmentally appropriate environment for children ages 15 months to 2 years and 9 months at the Undermountain Childcare Center at Berkshire School. This role works collaboratively with colleagues and families to promote children’s social, emotional, physical, and cognitive development in a licensed childcare setting.
Job Functions/Major Responsibilities:
- Provide attentive, responsive care to toddlers in a developmentally appropriate learning environment.
- Support children’s social, emotional, physical, and cognitive development through age-appropriate activities and routines.
- Maintain consistent supervision to ensure children’s safety at all times.
- Maintain a safe, clean, and organized classroom environment.
- Follow all Massachusetts EEC licensing requirements, health regulations, and safety protocols.
- Communicate regularly and professionally with families regarding children’s daily experiences and needs.
- Work collaboratively with fellow teachers and staff.
- Participate in staff meetings, training, and professional development opportunities.
- Perform other duties as assigned in support of the Undermountain Childcare Center.
Knowledge/Skills/Competencies:
- Minimum of one year of childcare experience in a licensed childcare facility.
- Knowledge of toddler development and developmentally appropriate practices.
- Strong communication and interpersonal skills.
- Ability to work effectively both independently and as part of a team.
- Commitment to maintaining a positive, inclusive, and supportive learning environment.
Physical Requirements:
- Ability to lift and carry children and materials up to 50 pounds, sit on the floor, stand, bend, and move frequently throughout the day, and respond quickly to children’s needs, including emergencies.
Other:
- Employment is contingent upon the successful completion of CORI/SORI and other background checks as required by Berkshire School and applicable law.
- Clean driving record.
Salary Range: $19.00–$25.00 per hour
How to Apply
FACULTY POSITIONS
Please send a cover letter of interest and resume to:
teaching@berkshireschool.org
STAFF POSITIONS
Please send a cover letter of interest and resume to Etienne Marofsky,
Director of Human Resources
emarofsky@berkshireschool.org
Phone: 413-229-1201
Berkshire School
245 N. Undermountain Road
Sheffield, MA 01257
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 (10% match)
• 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)
• Access to Dining Hall
• Use of athletic facilities and equipment (includes indoor exercise facilities and outdoor track)


