Regional Floating School Admin Leader

Guidepost Montessori; Chicago (IL); On-site; USD 33,000 - 41,000; Part time

Job summary

Guidepost Montessori is seeking an experienced Floating School Admin Independent Contractor to lead daily operations across campuses in the region, stepping in for leaves or staffing gaps and partnering with the Head of School.

You will cultivate relationships with families, mentor staff, and ensure a positive experience for children, families, and educators with calm, experienced leadership.

Qualifications

• Previous leadership experience in an early childhood education or school setting.
• Experience as a School Director, Assistant Director, Principal, Program Director, or similar leadership role.
• Proven ability to lead confidently with minimal direction.
• Strong organizational and operational management skills.
• Excellent communication and relationship-building abilities.
• Experience supporting admissions, enrollment, or customer service.
• Comfortable using technology, CRM systems, and administrative software.
• Collaborative leadership style with a solutions-focused mindset.
• Passion for supporting children, educators, and families.

Responsibilities

• Partner with Heads of School to oversee daily campus operations across the region.
• Build strong relationships with current and prospective families and guide tours and admissions.
• Support enrollment growth by managing inquiries and following up with prospective families in our CRM.
• Foster a positive, collaborative staff culture through coaching and day-to-day support.
• Resolve parent concerns with professionalism, empathy, and sound judgment.
• Coordinate community events and outreach to strengthen family engagement.
• Oversee operational needs such as vendor scheduling, supply orders, billing support, and campus organization.

Skills

Leadership

Communication

Relationships

CRM systems

Administrative software

Problem solving

Education

Director Qualified in Early Childhood Education

Tools

Salesforce

Job description

Guidepost Montessori is seeking an experienced Floating School Admin Independent Contractor to lead daily operations across campuses in the region, stepping in for leaves or staffing gaps and partnering with the Head of School.

You will cultivate relationships with families, mentor staff, and ensure a positive experience for children, families, and educators with calm, experienced leadership.