Director of Senior School![:0]()
Shape the Future of Learning. Lead with Purpose
Pickering College is more than a place to teach - it’s a vibrant community where educators grow, collaborate, and inspire. As Canada’s only Quaker-founded independent day and boarding school for JK to Grade 12, we provide a dynamic environment that empowers teachers to bring learning to life and make a lasting difference for students and the wider world.
Guided by our values of Simplicity, Peace, Integrity, Community, Equality, and Stewardship, our culture is built on purpose, respect, and collaboration. These principles shape not only the student experience but also the workplace setting, creating a supportive environment where educators thrive both personally and professionally.
Reporting to the Assistant Head, Academics and Student Programs the Director of Senior School provides leadership and management of the students and faculty in the Senior School so that the tone, culture and environment is maintained and models the values and mission of Pickering College. This is a unique opportunity for an experienced educator and school leader who combines strategic thinking with operational expertise, instructional leadership, and a deep commitment to student wellbeing. The successful candidate will lead a dynamic team of educators, foster meaningful relationships with students and families, and help shape the future direction of our school.
Core Areas of Leadership
Lead with Vision
· Champion the school's mission, vision, and values.
· Develop and communicate a compelling vision for the Senior School that inspires students to discover their passions and lead purposeful lives
· Lead the implementation of strategic initiatives and programs.
· Contribute to whole-school leadership and decision-making.
Advance Academic Excellence
· Promote a culture of high expectations, innovation, and continuous improvement.
· Support curriculum development, program evaluation, and academic growth.
· Supervise, mentor, and develop faculty and instructional leaders.
· Ensure academic programs meet and exceed Ministry standards.
Manage School Operations
· Oversee daily Senior School operations, schedules, timetables, and key academic processes.
· Coordinate major school events, examinations, graduation, and reporting periods.
· Manage resource allocation, facilities planning, and operational effectiveness.
· Support budget development and responsible stewardship of resources.
Champion Student Success
· Promote student wellbeing, engagement, belonging, and achievement.
· Oversee student support systems and interventions.
· Ensure student behavior and discipline reflect school values and policies.
· Support student leadership and character development initiatives.
Build Strong Relationships
· Foster a positive, inclusive, and welcoming school culture.
· Develop trusted partnerships with students, families, faculty, and community stakeholders.
· Address concerns with professionalism, empathy, and fairness.
· Represent the Senior School at school and community events.
Develop People and Build Teams
· Recruit, mentor, supervise, and evaluate faculty and staff.
· Support professional growth and leadership development.
· Build collaborative, high-performing teams.
· Promote faculty engagement, accountability, and retention.
Lead Change and Innovation
· Encourage innovation in teaching, learning, and operations.
· Drive continuous improvement by envisioning and implementing programs that will shape the student experience so that students have both the ability and responsibility to make a difference in the world.
· Lead school improvement initiatives and organizational change.
· Anticipate challenges and develop proactive solutions.
Qualifications & Experience
· Bachelor of Education, Intermediate/Senior, OCT
· Master’s in education an asset.
· Ontario Principal Qualifications (or equivalent leadership qualifications).
· Significant leadership experience in a Senior School, secondary school, or independent school setting.
· Demonstrated success leading faculty, academic programs, and school operations.
· Strong understanding of curriculum development, assessment practices, and student support systems.
· Experience managing complex initiatives, budgets, and multiple priorities.
Key Competencies
The successful candidate will demonstrate:
· Strategic and visionary leadership
· Instructional leadership and commitment to academic excellence
· Exceptional relationship-building and communication skills
· Operational and organizational effectiveness
· Student-centred decision-making
· Talent development and people leadership
· Collaboration and team effectiveness
· Strong stakeholder management capabilities
· Change leadership and innovation
· Sound judgment, professionalism, and integrity
Pickering College provides a competitive compensation package, including a Health Benefits Plan and participation in the Ontario Teachers’ Pension Plan.
Pickering College is committed to building and sustaining a pluralistic community. We actively seek students, families, faculty, and staff of varied backgrounds and encourage them to share their unique gifts to cultivate a rich educational environment. We strive to create a learning environment that exposes students to the value and breadth of differences, informs their perspective, and prepares them to shape the world.
As a condition of employment, the successful candidate(s) must provide a current Vulnerable Sector Screening Police Report. Suitable accommodations are available for applicants with accessibility needs due to disability upon request.
If you would like to be considered for this exciting opportunity, submit your cover letter and resume to humanresources@pickeringcollege.on.ca AI is not used during the interview process.
