Floating School Admin

Guidepost Montessori • Chicago, IL

18h

About The Position

Guidepost Montessori is hiring an experienced, adaptable Floating School Leader to support multiple schools in the Chicago area. The role works across several schools in partnership with school and regional leadership, providing leadership support wherever it is most needed. Depending on each school’s needs, the Floating School Leader may lead a school day to day, support an existing leadership team, or guide a school through a transition. The goal is to maintain a high-quality learning experience for children, exceptional service for families, and a supportive, collaborative workplace for staff. The ideal candidate is flexible, steady under pressure, and able to build trust quickly with new teams and families.

Guidepost Montessori is committed to expanding high-fidelity, authentic Montessori programs. Its educational model aims to foster independence and develop competent, capable, action-oriented thinkers and change agents.

Requirements

• 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 area, sometimes with short notice.
• Flexibility to adapt to different schools, teams, and schedules.
• Ability to connect with people and build relationships quickly.
• Strong organizational skills.
• Exceptional written and verbal communication skills.
• Strong attention to detail and a focus on results.
• Facility with computer systems.
• A high degree of personal initiative.

Nice To Haves

• 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 to inform marketing efforts.

Responsibilities

• Lead or co-lead assigned schools during leadership vacancies, leaves, absences, or periods of high need.
• Ensure schools remain in licensing compliance, including staff-to-child ratios, staff qualifications, and required documentation.
• Build and sustain a campus culture that reflects the organization’s mission.
• Manage day-to-day operations, including billing, supply ordering, maintenance scheduling, and staff scheduling.
• Support enrollment by giving tours, following up with prospective families, and managing leads in the CRM system.
• Build relationships with parents, answer questions, and resolve concerns.
• Support and coach staff and newer leaders, and share best practices across schools.
• Assist with special projects, events, and transitions across the region as needed.

Benefits

• Ongoing professional development.
• A network of supportive peers and mentors who regularly share best practices.
• Career growth and promotion opportunities, with exposure to multiple schools and leadership styles.
• Competitive salary.
• Health, dental, and vision insurance.
• Paid time off and paid holidays.
• 75% tuition discount for two children at any school within the network, which serves children from 3 months through 6 years old.
• Opportunity to contribute to a high-quality educational program that serves the individual needs of each child.

What This Job Offers

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