DEPUTY HEAD

Commencing in July 2026
Permanent - Full-Time

 Located in the heart of Toronto, The Bishop Strachan School (BSS) is a world-class independent JK to Grade 12 day and boarding school for girls. Home to 960 students (75 of whom are boarders), BSS is celebrated for its welcoming community, outstanding programs, and bold vision: to be an inspirational force for women to reach their full potential as transformative leaders, shaping a brighter and more inclusive future. For more than 150 years, BSS has inspired its students to be fearless and has educated them to be leaders. Through its challenging academic program, its exceptional range of co-curricular offerings, and its outstanding faculty and staff, the school has a focus on the Signature of a BSS girl. For more information about BSS and its exciting vision for the future, please see their current strategic plan.

We are looking for a dynamic and visionary educational leader, who will be a close partner with the Head of School. The Deputy Head will ensure that the School's Mission and Vision are realized in all programs for students fostering their academic, artistic, athletic and personal development. This perceptive and enterprising leader will champion creativity and innovation across the school, while facilitating wide administrative management of the educational program.

 This role supports the School’s vision to be a world leader in girls’ education by overseeing the full student experience. Through strategic leadership, the Deputy Head will help shape an innovative and relevant academic and co-curricular program that equips students to become confident leaders. 

 As the Deputy Head of School you will:

• Enthusiastically engage in the realization of the school's ambitious strategic plan, ensuring alignment with the overall mission and vision.
• Provide analytical and decision-making support to the Head, offering insights and recommendations on various strategic and operational matters.
• Energetically oversee the student experience at BSS from JK-Grade 12 in academics and student life programs, including knowledge and enthusiasm for best-in-class programs.
• Inspire, champion, articulate the value of change and drive change management processes to  influence others to embrace innovation and meet goals and objectives.
• Assist in the day-to-day operations of the school, including managing budgets, allocating resources, and implementing efficient administrative processes.
• Lead the analysis of key data indicators and other relevant metrics to assess the school’s performance.
• Collaborate with the Executive Director, Human Resources in recruitment, hiring, onboarding and retention of high-quality educators, as well as in leadership development and performance management.
• Collaborates with the Executive Director, Enrolment Management on recruitment and onboarding of new students, and active retention of current students.
• Collaborates with the Executive Director, Advancement on the strategic philanthropic priorities of the school and ensuring that they align with the school’s strategic priorities and the mission. 
• Participates on the Senior Leadership Team (SLT).
• Oversee student discipline and code of conduct across the whole school, including student incident reporting, and manage challenging situations with diplomacy and respect. 
• Provide leadership and inspiration in fostering a culture of excellence and innovation, while cultivating leadership in others through exceptional interpersonal skills.
• Represent the School in various speaking and promotional activities and events.
• Champion inclusion and belonging in all activities to foster a positive school culture that supports the well-being and growth of each student and employee.

The ideal candidate will have a bold vision for contemporary girls’ education with the experience and knowledge of research-informed practices to champion female leadership. Key proven abilities will include exceptional interpersonal skills and experienced people management, the ability to demonstrate strong leadership and engagement with the community.

How to Apply
Interested and qualified candidates are invited to submit a cover letter and resume in a single PDF file by email to Monika Mrowinski, Senior Talent Acquisition Specialist at mmrowinski@bedfordgroup.com.

We thank all applicants for their interest; however, only those selected for an interview will be contacted.

The Bishop Strachan School is an equal opportunity employer and is committed to fostering an inclusive, barrier-free environment in accordance with the Accessibility for Ontarians with Disabilities Act (AODA). Accommodations are available throughout the recruitment process. If you require accommodation at any stage, please contact Samantha Galati, Principal at 416-963-9000 ext. 260 or by email to sgalati@bedfordgroup.com.

The Bishop Strachan School and Bedford|TRANSEARCH are committed to building a diverse and inclusive workplace where everyone feels respected and empowered to succeed. We encourage applications from all qualified individuals, including but not limited to: women, persons of colour, Indigenous peoples, persons with disabilities, members of the 2SLGBTQ+ community, and others who reflect the diversity of our communities.

About The Bishop Strachan School

Founded in 1867, The Bishop Strachan School (BSS) is Canada’s oldest day and boarding school for girls, offering rigorous academic programs and a full co-curricular program to challenge and inspire every student. With an expert faculty, skilled staff, state-of-the-art resources, and a dynamic and supportive environment, BSS is a leading school for girls in Junior Kindergarten to Grade 12, and an exceptional workplace for those committed to excellence, innovation and continuous learning.

Connections working at The Bishop Strachan School