School Leadership

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