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Executive Administrative Assistant

Montessori School of the Berkshires
Lenox, MA Full Time
POSTED ON 11/25/2025
AVAILABLE BEFORE 3/24/2026

Berkshire Montessori School Executive Assistant Job Description

Job Title: Executive Assistant to the Head of School Department: Administration

Reports to: Head of School Effective Date: TBD

Classification: Full-time/Salary/Exempt Salary Range: $45,000 - $55,000

Job Summary:

The Executive Assistant provides high-level administrative and strategic support for the Head of School, serving as the primary liaison for internal and external stakeholders. This role ensures the effective operation of the Head’s office, maintains confidentiality, handles communication, and supports the implementation of the school’s mission and leadership priorities.

Essential Functions:

  • Manage the Head of School’s calendar, appointments, travel arrangements, and correspondence.
  • Serve as the primary point of contact for board members, faculty, parents, and community partners on matters relating to the Head of School.
  • Draft, proofread, and format communications, presentations, reports, and meeting minutes.
  • Organize and coordinate board meetings, events, executive retreats, and other school-wide functions.
  • Maintain electronic and paper files for easy retrieval of critical documents.
  • ​Process confidential and sensitive information with discretion and professionalism.
  • Assist with special projects, research, and goal tracking as directed by the Head of School.
  • Liaise with HR, business, admissions, advancement, and other departments as necessary.
  • Support school-wide communications and initiatives related to advancement, admissions, and event planning as assigned.
  • Manage basic bookkeeping for the Head’s office and reconcile expense reports.

Additional Duties

  • Attend appropriate faculty meetings and in-services.
  • Participate in the annual professional review process.
  • Complete and maintain all records, reports, evaluations, and inventories promptly as the school may require.
  • Frequently communicate with children and adults.
  • Attend to any other duties the Head of School assigns.
  • Contribute to the health and wellness of the MSB community with a strong sense of purpose, humor, grace, and courtesy.

Knowledge, Skills, and Abilities

  • Strong interpersonal and communication skills, with the ability to effectively collaborate with colleagues, parents, and students.
  • Read, work, and conduct oneself in accordance with the Staff Handbook and Crisis Manual guidelines.
  • Complete CPR and First Aid training.
  • Understanding and supporting the school’s mission, purposes, objectives, and policies in a positive and supportive manner.
  • Ability to anticipate needs and proactively address them.
  • Discretion and tact in handling confidential information.
  • Commitment to the values and mission of the school.

Qualifications

  • Bachelor’s degree or equivalent experience preferred.
  • Executive or senior administrative support experience, preferably in a school or nonprofit environment.
  • Excellent written and verbal communication skills; proven ability to draft and edit documents to high standards.
  • Strong organizational and time-management abilities; adept at managing multiple priorities.
  • Competent in Microsoft Office Suite, Google Workspace, and various online productivity tools.
  • High level of integrity, sound judgment, and professionalism.

Physical Requirements

  • Be able to lift 50 lbs.
  • Substantial movement of the wrists, hands, and/or fingers.
  • Work in indoor and outdoor environmental conditions.
  • Ability to sit/squat, stand, walk, and move to maintain eye level with students.

Travel Requirements
Limited travel to and from meetings may be required.

Note: The above description illustrates tasks and responsibilities. It is not meant to include every task or responsibility.

Pay: $45,000.00 - $55,000.00 per year

Benefits:

  • 401(k)
  • 401(k) matching
  • Dental insurance
  • Flexible spending account
  • Health insurance
  • Life insurance
  • Paid time off
  • Professional development assistance

Work Location: In person

Salary : $45,000 - $55,000

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