School Leadership

Posted Yesterday
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Chicago metropolitan area, Chicago, IL, USA
In-Office
70K-85K Annually
Senior level
Edtech • Kids + Family
The Role
Lead and develop campus teams to deliver high-quality Montessori early childhood education. Responsibilities include hiring and staff development, building school culture, supporting enrollment and family engagement, partnering with regional leaders on operations and sustainability, and making data-informed decisions that balance educational excellence and school performance.
Summary Generated by Built In
We are always looking to connect with experienced School Leaders across the Downtown Chicago and surrounding Illinois Suburb areas 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 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:

  • Hiring, leading, and developing a team of educators and staff
  • Building a strong, mission-aligned school culture 
  • Supporting enrollment growth and family engagement 
  • Partnering with regional and campus leaders to support operational health and sustainability 
  • Making thoughtful decisions that balance educational excellence and school performance  

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 $70,000 - $85,000 depending on qualifications 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 you if you possess:

  • DCFS Director Requirements 
  • Early childhood education leadership experience
  • Strong organizational skills and attention to detail with a focus on results
  • 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 will prefer you over other candidates if you have:

  • Experience teaching within a early childhood education setting
  • Experience in school leadership roles such as Head of School, Assistant Head of School, Early Childhood Program Director, or similar positions 
  • Familiarity with the Montessori method of education or a Montessori certification

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

  • DCFS Director Requirements
  • Early childhood education leadership experience
  • Strong organizational skills and attention to detail with a focus on results
  • Exceptional written and verbal communication skills
  • Aptitude for creating a warm and benevolent team culture
  • Strong leadership and ability to make tough decisions with limited information
  • Passion for Montessori pedagogy
  • Experience teaching within an early childhood education setting
  • Experience in school leadership roles (Head of School, Assistant Head, Program Director)
  • Familiarity with Montessori method or Montessori certification
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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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