Floating School Admin

We’re now hiring an experienced, adaptable leader to join our growing team as a Floating School Leader, supporting multiple schools in the Chicago 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 We believe that the traditional method of education used in most schools is antiquated, outdated, and broken.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 Floating School Leader works across several schools, partnering with school and regional leadership to step in wherever leadership support is needed most. Depending on each school’s needs, this person may lead a school day to day, support an existing leadership team, or guide a school through a period of transition. The goal is that every school keeps giving children a high-quality learning experience, giving families exceptional service, and giving staff a supportive, collaborative place to work. The ideal candidate is flexible, steady under pressure, and quick to build trust with new teams and families. Key responsibilities include, but are not limited to:

• Leading or co-leading assigned schools during leadership vacancies, leaves, absences, or periods of high need
• Making sure each school stays in licensing compliance, including ratios, staff qualifications, and required documentation
• Building and sustaining a strong campus culture that embodies the mission of our organization
• Managing day-to-day operations: billing, supply ordering, scheduling maintenance, and staff scheduling
• Supporting enrollment by giving tours, following up with prospective families, and managing leads in our CRM system
• Building relationships with parents, answering questions, and resolving concerns as they come up
• Supporting and coaching staff and newer leaders, and sharing best practices across schools
• Helping with special projects, events, and transitions across the region as needed

• DCFS Director qualified
• Leadership or management experience, ideally in early childhood education or a school setting
• Reliable transportation and willingness to travel between schools in the {XYZ} area, sometimes with short notice
• Flexibility to adapt to different schools, teams, and schedules
• An affinity for connecting with people and building relationships quickly
• Strong organizational skills
• Exceptional written and verbal communication skills
• Strong attention to detail with a focus on results
• Facility with computer systems
• A high degree of personal initiative

• Experience as a Director, Assistant Director, Program Director, or Admissions/Administrative lead at a preschool or school
• Experience supporting or overseeing multiple sites
• Familiarity with the Montessori method of education or a Montessori certification
• Experience working with Salesforce/CRM and billing software
• Knowledge of the local community that will inform marketing efforts