School Leadership

Guidepost Montessori • Chicago, IL

7d • $70,000 - $85,000

About The Position

Guidepost Montessori is seeking to connect with experienced school leaders interested in future leadership opportunities across Downtown Chicago and surrounding Illinois suburbs. School Leaders help build strong teams, cultivate thriving school communities, and ensure high-quality educational experiences for children and families. Depending on the opportunity, the role may involve leading campus teams, supporting enrollment health, fostering family relationships, and maintaining operational and program excellence. The position offers a competitive salary of $70,000–$85,000, depending on qualifications and experience, along with professional development, career growth opportunities, and benefits. Guidepost Global Education and Guidepost Montessori are equal opportunity employers and will reasonably accommodate employees and applicants with disabilities or special needs when requested.

Requirements

• Meet DCFS Director Requirements.
• Have early childhood education leadership experience.
• Demonstrate strong organizational skills and attention to detail with a focus on results.
• Have exceptional written and verbal communication skills.
• Show aptitude for creating a warm and benevolent team culture.
• Demonstrate strong leadership and the ability to make difficult decisions with limited information.
• Have a passion for getting education right through the Montessori pedagogy.

Nice To Haves

• Experience teaching in an 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.

Responsibilities

• Hire, lead, and develop a team of educators and staff.
• Build a strong, mission-aligned school culture.
• Support enrollment growth and family engagement.
• Partner with regional and campus leaders to support operational health and sustainability.
• Make thoughtful decisions that balance educational excellence and school performance.
• Depending on the opportunity, lead campus teams, support enrollment health, foster family relationships, and ensure operational and program excellence.

Benefits

• Ongoing professional development.
• Supportive network of peers and mentors who regularly share best practices.
• Career growth and promotion opportunities.
• 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 the network.
• Opportunity to contribute to a high-quality educational program serving the individual needs of each child.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed