School Leadership

Posted 4 Days Ago
Be an Early Applicant
Chicago, IL, USA
In-Office
50K-60K Annually
Senior level
Edtech • Kids + Family
The Role
Lead campus teams and operations for Guidepost Montessori schools in downtown Chicago, managing enrollment, family relationships, community outreach, billing and facilities coordination. Ensure mission-aligned culture, high-quality classroom experiences, and use CRM/billing systems to track leads and enrollment. Partner with regional leaders to support school performance and staff development.
Summary Generated by Built In
We are always looking to connect with experienced School Leaders across the Downtown Chicago area 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
  • 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 requirements
  • 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.

Skills Required

  • Meet Illinois DCFS director requirements
  • Experience in early childhood education, school operations, admissions, or leadership roles
  • 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
  • Strong attention to detail and follow-through
  • Comfortable using systems and learning new tools
  • Willingness to take initiative and step in where support is needed
  • 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
Am I A Good Fit?
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The Company
1,339 Employees

What We Do

Guidepost Montessori is a global network of high-quality Montessori schools and child care programs dedicated to fostering children's independence through authentic, child-paced learning. Serving students from birth to age 18, the organization operates over 90 campuses across the United States and internationally, providing nurturing environments and personalized care aimed at helping every child thrive in a structured Montessori setting.

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