We're now hiring an Administrative Assistant to join our founding team as we open a new 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 We believe that the traditional method of education used in most schools is antiquated, outdated, and broken.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 Administrative Assistant Position:

During the pre-open phase, the Administrative Assistant will support with the front desk, administrative work, and customer service operations. Once the school opens, there will be an opportunity for this position to grow into an Assistant Head of School role taking on responsibilities that 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:

  • 100% tuition discount for two children at any school within our network (we serve children 3 months through 12th grade)
  • 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
  • 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
  • Previous customer service or administrative experience
  • Are comfortable with technology and learning new systems quickly

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 

Please note that this position will be required to support in the classroom, working with the children for over 50% of the time. They will also be responsible for closing the school. We will not be accepting resumes or scheduling interviews through phone calls. 

Guidepost Montessori is a project of Higher Ground Education. You can learn more about our mission by visiting http://tohigherground.com/ 

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.

Apply for this Job

* Required

resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)


Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Guidepost Montessori’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.


Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.


Enter the verification code sent to to confirm you are not a robot, then submit your application.

This application was flagged as potential bot traffic. To resubmit your application, turn off any VPNs, clear the browser's cache and cookies, or try another browser. If you still can't submit it, contact our support team through the help center.