Full time Middle School Teacher position (Grades 7–8)

We are seeking an experienced, self-directed Middle School Teacher who is skilled at designing curriculum and creating engaging, meaningful learning experiences.

Our Middle School teacher develops and delivers the curriculum across the core subjects: English, math, science, history and geography. The teacher designs units, projects and assessments that align with Ontario expectations. This role is best suited to an educator who has built curriculum before and finds that work energizing. Candidates who prefer to teach from an established program may find a different setting a better fit.

Our program is grounded in Maria Montessori’s vision for the adolescent. Montessori saw early adolescence as a distinct stage of development, a time when young people are building their sense of self in relation to society and need real work, real responsibility and a real place in their community.

Our Middle

School reflects this through leadership roles within the school, community service, hands-on projects and time on the land, alongside rigorous academic work. Students are treated as capable young people whose contributions matter.

Our Middle School cohort is small, allowing the teacher to know each student well and to shape a program around their interests, needs and growth. Teachers are offered significant professional autonomy. They are encouraged to bring their own strengths and passions into the classroom.

Our rural campus includes forests, meadows, marshland and gardens, with easy access to the Hockley Valley trail system. Outdoor and experiential education are central to how we teach.

We believe education involves the development of the whole child. Social and emotional growth, healthy relationships, self-awareness and character development are valued alongside academic achievement.



We are looking for someone who balances firmness with warmth and respect, sets clear expectations, and builds strong relationships with adolescents.

Responsibilities

Design and teach curriculum across all core subjects for Grades 7 and 8. Develop and lead student leadership opportunities and community service initiatives. Assess student progress, provide meaningful feedback and write progress reports. Communicate effectively with parents. Plan and participate in field trips, outdoor education and school events. Collaborate with colleagues to support students and school initiatives.

Qualifications

Previous teaching experience with middle school-aged students, with demonstrated experience developing curriculum. Strong command of the core subject areas, including Grade 7–8 mathematics. Solid classroom management and relationship-building skills. Excellent organizational and communication skills.

Montessori Adolescent training is a strong asset, as is Upper Elementary training. We also welcome applications from OCT-certified teachers, IB educators and other experienced educators who are drawn to Montessori’s vision of adolescence and interested in growing into it.

We Offer A collaborative and supportive staff culture, a small class size, significant qualified autonomy, a beautiful natural campus, ongoing professional development, and the opportunity to contribute to the continued growth of the school.

Start date is flexible, from November through early January.

To Apply

Please send your resume and cover letter

Job Type: Full-time

Pay: $5,000.00-$7,000.00 per month

Application question(s)

- Where do you currently live?
- Why do you think Headwater Hills Montessori school would be a good fit for you?

Education:
- Bachelor's Degree (required)

Experience:
- Teaching: 2 years (preferred)

Language:
- English (required)

Location:
- Caledon, ON (preferred)

Work Location: In person

📌 Middle School Teacher (Caledon)
🏢 Headwater Hills Montessori
📍 Caledon