Job Category: Guidepost Academy
Job Type: Part Time
Job Location: Ontario Toronto

Teachers who want to change the world come to Guidepost Academy .

Guidepost is a school dedicated to a union of classical and Montessori approaches to education: An emphasis on history and outstanding books, with a Montessori reverence for independence and agency.

We are looking for a Part Time Middle School Math Teacher for the school year.

Changing the world is in our DNA. Our organization was founded to do just that—a group of educators and likeminded individuals had caught a glimpse of what could be possible in education, and wanted to bring it to the world. Education today is filled with false alternatives. We disrupt them all. Our vision is a classroom where students plumb the depths of human knowledge and aspire to the height of intellectualism—and do it all at their own self-direction. Do you believe that there is critical, life‑shaping knowledge that children desperately need—but also believe that they need to be in the driver’s seat when they pursue it? Then Guidepost Academy is the place for you.

Our Montessori approach means we believe in promoting each student’s individual agency. This includes open‑ended, free work periods, where students choose what to work on and work at their own pace. We bring structure to that through a coaching‑based approach that helps students plan their own goals for the day and week, using adults as guides and accountability partners.

This approach takes work to learn, so you’ll need to come in with that attitude. It also takes flexibility and a willingness to adapt. You will be joining a team of ambitious, creative, and inspiring educators and a fast‑paced organization with opportunities for growth and development.

Your Role





- Facilitate student progression through coursework through regular feedback and support
- Establishing and modeling a strong, supportive community that upholds GPA’s core values at all times
- Working closely with your colleagues on campus to continually improve the program and support our students
- Partner with parents to ensure students are fully supported at home and at school

We Would Love To Talk To You If You

- Have a demonstrated passion for and experience in teaching mathematics
- Have exceptional written and verbal communication skills
- Are looking to co‑create a vibrant, thriving, loving school community
- Are an experienced mentor of adolescents who wants to help individual students explore their passions, overcome challenges, and surpass expectations
- Are interested in joining a growing, evolving, and ambitious educational program

About You

We strongly encourage and welcome people from all educational and professional backgrounds to apply for this opportunity and join our unique community. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. What unites us is a passion for subject matter and a deep reverence for and belief in our students.

About Us

Our culture is built on five core values:

The Pursuit of Truth: We pursue knowledge not as an academic exercise, but to improve our judgement and actions in the world. We believe that understanding what is true matters, and we pursue deeper understanding whenever possible.





The Power of Agency: We believe that human beings, using their reason, judgement, and passion, are capable of leading self‑directed lives of profound meaning and worth. We seek to develop and exercise our capacity to act with purpose, integrity, and conviction in pursuit of our aspirations.

The Love of Work: Purposeful work is central to a life well‑lived. In choosing our work, we direct our energies intentionally toward our goals, bring structure and focus to our lives, and reshape our worlds. Through cultivating our capacity for work, as well as our appreciation of the rewards of work well done, we develop a character capable of genuine effort and great achievement.

The Joy of Community: We recognize the value of deep, honest relationships, and we offer others an authentic self that makes such relationships possible. We enliven and enrich each other through our choice to share norms, practices and expectations. In doing so, we experience the joy of belonging and develop a deep and abiding sense of love and responsibility for the communities we embrace.

The Courage to Live Wholeheartedly: To fully engage with the world requires a tremendous amount of vulnerability and moral courage. In order to become our best selves, we bravely face our insecurities and have the courage to care deeply about our values.

Guidepost Academy is committed to a policy of equal employment opportunity. We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, disability or any other legally recognized protected basis under applicable laws. Our leadership is dedicated to ensuring the fulfillment of this policy.

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📌 Part Time Middle School Math Teacher (Toronto)
🏢 Montessori Teachers College
📍 Toronto