Location- in person
Position Type-Full Time ( Replacement )
Reports to: Deputy Head, Academics
Position Type: Leadership, Full-Time
Compensation & Placement: $145,000 to $165,000. Total compensation for the Head of Middle School is calculated based on placement within the HTS faculty grid. Final salary placement will be determined by recognized years of teaching experience, academic credentials, and Additional Qualifications (AQs).
No AI is used for screening, assessment, or selection.
Join the Movement: Co-Create the Future of Education at HTS.
Head of Middle School
Holy Trinity School (HTS) is not just an independent school in the heart of Richmond Hill just 25 minutes north of downtown Toronto, it is an incubator for purpose and an engine for change. From Junior Kindergarten to Grade 12, we are committed to a shared journey of discovery, anchored by a fiercely personalized experience that places every learner at the centre.
We are a connective community built on the unwavering values of Respect, Courage, and Integrity, fostering an environment of warmth, care, and joyful learning. But our story is one of action and innovation. Founded by visionary pioneers 44 years ago, HTS continues to lead with an entrepreneurial spirit, believing that preparing for the future requires reimagining what school can be.
Innovation here is deeply human and authentic. It’s the transformation we spark in our people. We empower every single member of our staff to unlearn, take risks, and co-create what's next. This is where big ideas are not just discussed; they are turned into reality through mindset, heart, and courage.
Your passion has a profound purpose here. Step into a culture where your voice contributes to a story of growth and belonging. We invite you to move beyond the status quo and help us redefine the educational landscape.
Come, be a part of the team driving this transformative era at Holy Trinity School.
Organizational Values:
Dignity is at the heart of inclusion and respect.
Learning is a journey, not a destination.
Character is the essence of our humanity.
Excellence is the pursuit and realization of one’s personal best.
Innovation is a mindset of possibilities fuelled by curiosity.
About this Leadership Role:
The Head of Middle School provides strategic, instructional, and operational leadership aligned with the school’s mission, vision, and strategic priorities. This role champions learner-driven, inquiry-based, and interdisciplinary teaching while ensuring strong alignment between curriculum, assessment, and instructional design. The leader supports the evolution of signature programs and oversees the development of a comprehensive social-emotional learning (SEL) framework, digital literacy, and emerging technology integration.
The role fosters a culture of belonging, respect, growth, and high expectations, prioritizing student wellbeing and a progressive, restorative approach to discipline. Working closely with faculty, counsellors, and families, the leader ensures consistent, equitable student support practices and serves as a key point of contact for student conduct matters.
The position mentors and develops faculty, supports recruitment and performance growth, and cultivates a collaborative professional culture. The role also oversees daily operations, including scheduling, staffing, admissions support, budgeting, and long-range planning, while maintaining strong communication across divisions.
The Head of Middle School serves as a visible and approachable presence within the community, building strong partnerships with families and contributing actively to whole-school initiatives and strategic conversations.
Who You Are:
At HTS, we believe schools are built by people and when people feel seen, supported, challenged, and trusted, extraordinary learning becomes possible.
The Head of Middle School provides visionary, relational, and instructional leadership for Grades 6–8, stewarding a learning environment where adolescents and faculty are known, challenged, supported, and inspired and parents are partners. This role is central to advancing HTS’s Learner-Driven Ecosystem, ensuring coherence between academic excellence, Student Life, student wellbeing, and character development during a pivotal stage of learner growth.
The Head of Middle School leads with a deep understanding and love of early adolescence, and delights in creating a vibrant school culture where students and staff can play, collaborate, and experiment together. The Head demonstrates a commitment to innovative and evidence-informed practice, and a belief that strong systems, relationships, and shared purpose enable both students and staff to thrive. They also partner strategically across the school to proactively cultivate a culture of inclusion and belonging amongst students and staff alike.
What You Need
We are inviting candidates with the following qualifications to apply:
Ontario College of Teachers certification in good standing
Principal’s Qualification Program, Part 1 with Part 2 completed by September 2026
Minimum 5 years of School leadership experience
Graduate degree in Education or a related field could be seen as an asset.
Demonstrated success in Middle School leadership and/or administration.
Deep understanding and love of adolescent development and effective Middle School pedagogy.
Experience leading instructional innovation, interdisciplinary learning, or learner-centred initiatives.
Strong relational leadership skills with the ability to balance care, accountability, and clarity.
Proven capacity for strategic thinking, systems leadership, and change management.
Alignment with HTS’s values, competencies, and learner-driven philosophy.
Experienced in utilizing cultural competencies in inclusive leadership, cross-cultural relationship management, and decision-making
What’s In It For You?
We offer a competitive compensation and benefits package including participation in the Ontario Teachers Pension Plan and provide the following:
Generous time off throughout the year, including during the summer.
Learners who are inspiring, dedicated and deeply committed to their learning and our community
A stimulating learning and work environment
Extensive professional learning opportunities
A beautiful and modern campus nestled in 37 acres of forest in the Oak Ridges Moraine
A professional culture based on the principles of integrity, professionalism and innovation
An environment that is committed to equity
Apply Now
If you are interested in joining us at our attractive Richmond Hill campus we encourage you to apply at www.hts.on.ca
The deadline is March 20, 2026 We thank all applicants for their interest; however, we will only contact those selected for an interview.
