Trinity College School

Headmaster Assistant

Position: Headmaster Assistant
Start: 2018-07-15
SchoolTrinity College School
City: Port Hope, Ontario

Posting Date: 2018-05-09

Trinity College School

Trinity College School

Connect with Trinity School

English Teacher

Trinity College School (TCS) is a leading co-educational boarding and day school for approximately 550 young people from Grades 5-12. Founded in 1865, the School places a balanced emphasis on academics, service learning, athletics and the arts – as both a long-held TCS tradition and a thoughtful approach to 21st century education.

Trinity College School is currently searching for an Assistant to the Headmaster to join our engaging school community. Reporting to the Headmaster, the Assistant to the Headmaster is expected to maintain a high level of professional competence and confidentiality and to be knowledgeable of best practices related to his/her areas of responsibility. This position is responsible for providing administrative support to the Headmaster which includes, but is not limited to, calendar management, reporting, internal and external communication, event coordination and other administrative tasks needed to support the Headmaster’s office. This is a permanent, full-time position with a mid-July start date.

Key Responsibilities

  • Provide administrative support for the Headmaster; oversee calendar maintenance, travel arrangements, financial reporting, correspondence, internal & external communications
  • Oversee and work with various departments in the School to ensure key school events are coordinated effectively; event requirements may include arrangements for information technology, food & beverage, venue set-up, invitations
  • Act as liaison with the offices of the Head of Senior School and the Head of Junior School
  • Take on special projects as requested

Requirements & Skills

  • Bachelor’s degree, preferred
  • Demonstrated experience in supporting an executive-level position, requiring the highest level of discretion and confidentiality
  • A commitment to customer service (both external and internal)
  • Ability to exercise excellent professional judgment, diplomacy and integrity
  • Well-developed communication skills and advanced writing & editing skills
  • Outstanding project management, customer service, multi-tasking & interpersonal skills
  • Ability to work under pressure, both independently and within a team
  • Strong computer skills & proficiency with Microsoft Office Suite; familiarity with Blackbaud, Google Docs and Spreadsheets

For a complete job description and position requirements, visit

To Apply: Submit your resume via email, no later than May 22nd, to:

The Office of the Headmaster, Trinity College School


Please clearly indicate the position you are applying for in the subject line of your email.

We thank all applicants for their interest, however, only those selected for interviews will be contacted. Trinity College School is an equal opportunity employer.

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