School Leadership

Overview

Guidepost Montessori is seeking to connect with accomplished school leaders for upcoming leadership opportunities in the Downtown Chicago area and nearby Illinois suburbs. These roles are suited to professionals who are passionate about Montessori education and have a record of creating strong teams, healthy school communities, and excellent learning experiences for children and families.

Role summary

Depending on the specific campus need, the School Leader may oversee campus teams, support enrollment stability, strengthen relationships with families, and help maintain operational and program quality across the school.

Key responsibilities

• Recruit, guide, and grow a team of educators and staff
• Develop and sustain a school culture that reflects the mission and values of the organization
• Help drive enrollment growth and deepen family engagement
• Work closely with regional and campus leadership to support operational stability and long-term sustainability
• Make balanced decisions that support both educational quality and overall school performance

What the organization offers

• Continuous professional development
• A supportive community of peers and mentors who regularly exchange effective practices
• Opportunities for career advancement and promotion
• A competitive annual salary in the range of $70,000 to $85,000, based on qualifications and experience
• Health, dental, and vision coverage
• Paid time off along with paid holidays
• A 75% tuition discount for two children enrolled in any school within the network, serving children from 3 months through 6 years of age
• The chance to help deliver a high-quality educational program tailored to each child’s individual needs

Eligibility and preferred profile

Candidates should meet DCFS Director requirements and bring leadership experience in early childhood education. Strong organization, careful attention to detail, results orientation, excellent written and verbal communication, and the ability to create a warm, supportive team environment are important. The role also calls for steady leadership, sound judgment when making difficult decisions with limited information, and a strong commitment to Montessori education.

Preferred background

Applicants with teaching experience in early childhood settings, prior school leadership experience such as Head of School, Assistant Head of School, or Early Childhood Program Director, and familiarity with Montessori education or Montessori certification will be given preference.

Equal opportunity statement

Guidepost Global Education and Guidepost Montessori are committed to equal employment opportunity. Hiring decisions are made without discrimination based on 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 protected status under applicable law. Reasonable accommodations may be provided for employees and applicants with disabilities or special needs upon request.