Assistant Head of School (Assistant Director)

Job Responsibility:

We're now hiring an experienced leader to join our growing team as Assistant Head of School in the Toronto, Ontario area!

Guidepost Montessori is a community of educators who are driven by a deep desire to bring about widespread change in education today. We believe that the traditional method of education used in most schools is antiquated, outdated, and broken. To meet the needs of today's students and to bring about true progress in the world around us, we need an education model that fosters independence and develops competent, capable, action-oriented thinkers and change agents. To that end, we are committed to dramatically increasing the amount of high-fidelity, authentic Montessori programs, not only in the U.S., but around the globe!

The Assistant Head of School Position:

The Assistant Head of School works closely with the Head of School to ensure that the school provides a high-quality learning experience for children, exceptional customer service to parents, and a supportive, collaborative work environment for staff. The ideal Assistant Head of School will love building community, working with parents, and leading community outreach initiatives. Key responsibilities include, but are not limited to:

• Supporting the creation of a strong culture on campus that embodies the mission of our organization
• Planning and hosting community outreach events
• Giving tours to prospective families, and converting leads to enrolled families
• Driving the enrollment process (managing leads utilizing a CRM system)
• Managing general, day-to-day operations for the school: billing, supply ordering, scheduling maintenance
• Interfacing with parents to build community, answer questions, and resolve any concerns that may arise

What we offer:

• Ongoing professional development
• A network of supportive peers and mentors who regularly share best practices
• Career growth and promotion opportunities
• A competitive salary
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 100% tuition discount for two children at any school within our network (we serve children 3 months through 12th grade)
• The opportunity to contribute to a high-quality educational program that serves the individual needs of each child

We'd love to talk to you if you possess :

• Obtained a Montessori diploma
• Earned a Bachelor's Degree in Early Childhood Education and is in good standing with the College of Early Childhood Educators
• Strong organizational skills and attention to detail with a focus on results
• Minimum of 2 years' providing licensed child care
• Exceptional written and verbal communication skills
• An aptitude for creating a warm and benevolent team culture
• Strong leadership and the ability to make the tough decisions with limited information
• A passion for getting education right through the Montessori pedagogy

We'd prefer you over other candidates if you have:

• Experience as an Admissions, Administrative, Program or School Director for a preschool
• Familiarity with the Montessori method of education or a Montessori certification
• Experience working with Salesforce/CRM and billing software
• Knowledge of the local community that will inform marketing effort

Guidepost Montessori is a project of Higher Ground Education. You can learn more about our mission by visiting

Higher Ground Education, Guidepost Montessori, and Academy of Thought and Industry are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation.