Executive Assistant

Staff / Full-Time

The Chestnut Hill School, Chestnut Hill, MA

The Executive Assistant will provide consistent, confidential, and professional administrative support for the Head of School and – as assigned – to other administrators, in order to maintain the well-being of the school and the broader community. The Executive Assistant will promote the school’s mission, making it the center of all decisions and actions, and serve as a source of information for students, families, and staff.

Head of School Support

  • Organize and review daily priorities 
  • Schedule, maintain, and confirm the Head of School’s appointments and calendar activities
  • Assist with preparation, documentation, technology, and catering in support of Board of Trustees meetings
  • Edit, proofread, and/or write communications on behalf of the Head of School
  • Travel arrangements as needed
  • Track and reconcile expenses by the Head of School
  • Special projects as assigned by the Head of School

Administrative Team Support

  • Lead Graduation and Grade 6 Farewell Dinner planning and execution
  • Support planning process for major school events which may include: Curriculum Night, Field Day, ISEE administration, Grandparents and Special Friends Day, MLK Service Day, Grade-level coffees
  • Support all offices when hiring, by creating hiring schedules, greeting candidates, and supporting the candidates throughout the day

All-School Support

  • Oversee all internal and external school calendars, room reservations, and scheduling of events; set Important Dates for future academic years 
  • Prepare a weekly internal newsletter detailing news and events 
  • Manage the Staff Support Budget
  • Oversee catering for all-staff lunches and celebratory events
  • Prepare new staff orientation and documents for the start of the school year (mailbox, office door signs, internal directory, etc.)
  • Provide coverage for front reception desk as needed
  • Provide support for general clerical duties and tasks as needed


  • Bachelor’s degree
  • Three to five years professional experience, academic environment a plus
  • Strong interpersonal skills and proven success at working collaboratively and efficiently on a creative and goal-oriented team
  • Decision-making and prioritization skills
  • Proven multi-tasker with high level of organization skills 
  • Exceptionally capable in both written and oral communication
  • Technologically savvy; proficient with Google and Microsoft Office Suites
  • Event planning skills
  • Dedication to a high level of confidentiality
  • Warm and personable with a good sense of humor 
  • High-energy and enthusiastic about working in a small school setting

Interested candidates should send a cover letter and resume to Lisa Halm, Director of Finance & HR, with “Executive Assistant” in the subject line to employment@tchs.org

The Chestnut Hill School

Chestnut Hill, MA
Early Childhood, Elementary
All Gender