Deputy Head of School

  • Bishop Strachan School
  • Toronto, ON, Canada
  • Jan 26, 2024
Full-Time Principal & Vice-Principal Senior Administration Superintendent

Job Description



Deputy Head of School

Toronto, Ontario


Canada’s oldest day and boarding independent school for girls, The Bishop Strachan School is a place of extraordinary scholastic and personal growth, in which the school’s 953 students work collaboratively, embrace the strength of differences, and learn to be leaders. The school’s unique, forward-looking, and research-informed approach to education is encapsulated in two signature documents: the Culture of Powerful Learning and the Signature of a BSS Girl. BSS expands hearts and minds, inspiring and challenging girls and young women from JK to Grade 12 to become intellectually curious, independent, courageous, compassionate, and creative global citizens – able to lead and navigate successfully our increasingly complex and inter-connected world.

Reporting to the Head of School, the Deputy Head will contribute to the realization of the school’s ambitious strategic plan, and provide analytical and decision-making support and insights to the Head of School. The Deputy Head will serve as a member of the senior leadership team and provide strategic and operational leadership to the school’s educational and student life teams. Working collaboratively with school principals, the Dean of Teaching and Learning, the Executive Director, Enrolment Management and Student Experience, and other team members, the Deputy Head will make a vital contribution to the successful realization of the academic, artistic, athletic, and personal development of every BSS student. 

You are a visionary educational leader who inspires others to work together to achieve aspirational goals. Your senior administrative leadership experience, exceptional interpersonal skills, and dynamic leadership qualities will further strengthen the BSS culture of creativity, innovation, collaboration, and academic excellence. Au courant with educational trends, curriculum development, and best practices, you are a lifelong learner with a growth mindset. You have a Master’s or Doctoral degree in Education or Educational Leadership, passion for and knowledge of girls' education, and experience in building a holistic student experience and academic program in a multi-division school. A perceptive systems thinker, you are at once analytical, data-driven, results-oriented, caring, and a champion of the principles of diversity, equity, inclusion, and belonging. This is an opportunity for a proven educational leader with a profound and contemporary understanding of curricular and co-curricular programs to lead all BSS students towards a confident future. 

BSS is committed to fostering an inclusive, diverse, and respectful environment, believing that diversity in the school fosters a rich, inclusive, and creative environment. BSS is actively engaged in building a more diverse school and encourages all qualified applicants to apply. The school is also committed to providing an accessible experience and an inclusive and barrier-free work environment, beginning with the recruitment process. If you have restrictions that need to be accommodated to fully participate in any phase of the recruitment process, please advise the Caldwell team in confidence. All responses to Caldwell are confidential. Please indicate your interest in Project 240139 with a cover letter and resume at