Burbank, California
Wallingford, Connecticut
Springfield, IL
Monticello, New York
Hood River, Oregon
Rosemont, Pennsylvania
San Bernardino, California
Posted: 18-Dec-25
Location: Weston, Massachusetts
Type: Full Time
Salary: 75,000-80,000
Required Education:
Date Posted: December 16, 2025 Starting Date: Spring 2026 Job Description: 12-month, full-time, exempt, in-person
The Cambridge School of Weston seeks an Executive Assistant to the Head of School. Reporting to the Head of School, the Executive Assistant provides high-level administrative support to the Head of School and serves as a key liaison between the Head’s Office, the Board of Trustees, and the broader school community. This position requires confidentiality, strong technical and organizational skills, professionalism, discretion, and the ability to manage multiple tasks efficiently in a fast-paced school environment.
Salary Range: $75,000-85,000
Specific Responsibilities for this Position Include:
Administrative Support:
- Manage the Head of School’s calendar, appointments, expense reports, and travel arrangements.
- Manage all appointment scheduling and travel arrangements that include both the Head of School and the Chief Development Officer.
- Prepare and/or edit correspondence, reports, presentations, and other documents.
- Organize and coordinate guest visits.
- Coordinate school-wide meetings, including faculty and leadership team meetings.
- Handle incoming communications, including phone calls and emails, and prioritize responses.
- Collaborate with the Director of Alumni and Parent Engagement in support and maintenance of school archives.
- Provide regular reception desk coverage.
- Perform various administrative tasks as needed.
Board & Committee Support:
- Serve as the liaison to the Board of Trustees, supporting the Board Chair, coordinating and attending meetings, and disseminating agendas and materials (both internally and on our school portal).
- Support board committees as needed.
- Prepare and distribute minutes and maintain all board-related records and documentation.
- Assist in event planning for board-related activities.
School Communications:
- Act as a primary contact for internal and external stakeholders on behalf of the Head of School.
- Represent the Office of the Head of School with professional, high-quality, verbal and non-verbal communications with faculty, staff, parents, students, and external organizations.
- Draft and edit correspondence and school announcements that come from the Office of the Head of School.
- Serve as a member of the school’s Calendar Committee.
Event Planning & Special Projects:
- Support the planning and execution of special school events and functions such as opening and closing meetings, weekly faculty and staff meetings, and special professional development days.
- Lead the planning and execution of Graduation and the faculty and staff end-of-year recognition program.
- Assist with projects assigned by the Head of School.
- Maintain a pulse on school activities and ensure the Head is informed and prepared.
Skills and Qualifications:
- Bachelor’s degree preferred.
- Minimum of 3-5 years of experience in an executive assistant or similar administrative role.
- Prior experience in an educational or nonprofit setting is preferred.
- Strong organizational and time management skills with exceptional attention to detail.
- Excellent verbal and written communication skills.
- Proficiency in Blackbaud (or understanding of Learning Management Systems), Microsoft Office Suite, Google Workspace preferred, and other administrative tools.
- Emerging understanding of the role of Artificial Intelligence in the workplace and willingness to be trained on its use.
- Ability to handle sensitive and confidential matters with discretion and professionalism.
- Flexibility and adaptability to handle a dynamic work environment.
- Strong interpersonal skills with the ability to build positive relationships across all school constituencies.
Work & Physical Requirements:
- Ability to work on campus during standard school hours with occasional evening and weekend events.
- Ability to sit, stand, and move around campus as needed.
- Ability to lift and carry materials up to 20 lbs when necessary.
Benefits of Working at CSW:
- Collegial faculty and working environment.
- Curricular agency valuing creativity, innovation, and collaboration.
- Competitive salary and robust human resource benefits.
- Funding and institutional support for professional development.
- Innovative daily and annual schedule that values reflection and relationship-building.
- Provided light breakfast items and hot lunch, as well as access to our state-of-the-art fitness center.
- Wooded, 65-acre campus located just 12 miles from Boston and Cambridge, in close proximity to scenic walking trails and excellent local restaurants and shops.
- Easy access to Kendal Green MBTA station, with on-campus parking and EV charging stations.
To Apply for this Position:
Interested candidates should submit a resume, cover letter, and references to execassistsearch@csw.org. Applications will be reviewed on a rolling basis beginning on January 12, 2026.
Deadline for Applications:
The position will remain open until filled.