School Leadership

guidepostmontessori· Assistant Head of School
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About this role

We are always looking to connect with experienced School Leaders across the Illinois Suburbs who are interested in future leadership opportunities within our Guidepost Montessori network! 

 

School Leadership Opportunities: 

We are looking to connect with experienced school leaders who share our passion for Montessori education and who have demonstrated success in building or supporting strong teams, cultivating thriving school communities, and ensuring high-quality educational experiences for children and families. 

Depending on the specific opportunity, School Leaders within our network may be responsible for leading campus teams, supporting enrollment health, fostering family relationships, and ensuring operational and program excellence. 

Responsibilities may include, but are not limited to:

  • Supporting a strong, mission-aligned culture on campus that reflects our values
  • Building relationships with families and creating a welcoming, high-quality school experience
  • Leading tours for prospective families and guiding them through the enrollment journey  
  • Managing the enrollment process, including lead tracking and follow-up through CRM systems
  • Planning and supporting community outreach events
  • Overseeing key aspects of day-to-day school operations, including billing, supply ordering, and facilities coordination
  • Responding to family questions and resolving concerns with professionalism and care
  • Partnering with school and regional leaders to support overall school performance and consistency  

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 of $50,000 - $60,000 depending on education and experience 
  • Health, dental, and vision insurance
  • Paid time off and paid holidays
  • 75% tuition discount for two children at any school within our network (we serve children 3 months through 6 years old)
  • The opportunity to contribute to a high-quality educational program that serves the individual needs of each child

We'd love to talk with candidates who:  

  • Meet Illinois DCFS Director Qualifications 
  • Have experience in early childhood education, school operations, admissions, or leadership roles
  • Are highly organized and able to manage multiple priorities effectively 
  • Enjoy working with families and building strong relationships
  • Communicate clearly and professionally, both verbally and in writing  
  • Have strong attention to detail and follow-through
  • Are comfortable using systems and learning new tools
  • Take initiative and are willing to step in where support is needed     

We'd prefer candidates who have:

  • Experience in roles such as school leadership, admissions, program management, or operations 
  • Familiarity with the Montessori method of education or Montessori certification
  • Experience using CRM systems and billing platforms 
  • Knowledge of the local community to support outreach and enrollment efforts 

Guidepost Global Education and Guidepost Montessori 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.

Frequently Asked Questions

Is the salary disclosed for the School Leadership position at guidepostmontessori?
The salary for this School Leadership role at guidepostmontessori is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the School Leadership position at guidepostmontessori located?
This School Leadership role at guidepostmontessori is based in Chicagoland Area - North Suburbs. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Which team or department does the School Leadership at guidepostmontessori belong to?
This School Leadership position is part of the Assistant Head of School department at guidepostmontessori. See the full job description for more information about the team structure and responsibilities.
How do I apply for the School Leadership position at guidepostmontessori?
Click the "Apply Now" button on this page. You will be redirected to guidepostmontessori's official application portal hosted on greenhouse where you can submit your application directly.
When was the School Leadership job at guidepostmontessori posted?
This School Leadership position at guidepostmontessori was posted on May 27, 2026. Apply as soon as possible — early applications are often reviewed first.
School Leadership
guidepostmontessori
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