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School Director

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Guidepost Montessori
Full Time position
Listed on 2026-01-03
Job specializations:
  • Education / Teaching
    Education Administration
  • Management
    Education Administration
Salary/Wage Range or Industry Benchmark: 70000 - 90000 USD Yearly USD 70000.00 90000.00 YEAR
Job Description & How to Apply Below
Position: School Director New

We're hiring experienced leaders to join our growing team as Head of School (School Director) in the Chicago, Illinois 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 We believe that the traditional method of education used in most schools is antiquated, outdated, and broken.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 Head of School Position

We are looking for a leader who shares our passion for the Montessori method and has the talent and perseverance required to quickly grow enrollment, attract and retain great staff, build a strong parent community, and ensure the educational experience for each child in every classroom is of the highest standard. As the Head of School,
you'll be responsible for providing leadership to the entire campus team.

Responsibilities include, but are not limited to:

  • Developing a strategic plan for the campus
  • Creating a strong culture that embodies the mission of our organization
  • Building a strong community among staff, parents, and children
  • Ensuring delivery of an exceptional program
  • Ensuring overall profitability targets are met (including managing campus budget)
  • Working with the Assistant Head of School to ensure enrollment targets are met
  • Hiring, supporting, developing, and managing teaching staff

What we offer:

  • A network of supportive peers and mentors who regularly share best practices
  • Career growth and promotion opportunities
  • 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 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:

  • 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 an early childhood education setting
  • Experience as an Admissions, Administrative, Program or School Director for a preschool
  • 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.

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