Regional Montessori School Ops Leader (Contract)

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

Benefits offered by this job

Flexible project-based contracts

Collaborative leadership with Head of

Opportunity to mentor campuses

Job summary

Guidepost Montessori is seeking an experienced Floating School Admin Independent Contractor to partner with the Head of School and lead daily operations across our U.S. campuses. Cover maternity leaves, support schools in transition, and fill leadership gaps with calm, experienced guidance.

The role focuses on problem-solving, staff coaching, family engagement, and maintaining smooth campus operations wherever you’re needed.

Qualifications

• Experience as a School Director or similar leadership role.
• Proven ability to lead with minimal direction.
• Strong organizational and operational management skills.
• Excellent communication and relationship-building abilities.
• Experience supporting admissions, enrollment, or customer service.
• Comfort with technology 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, including maternity leaves and staffing gaps.
• Build relationships with families and guide them through tours and admissions.
• Support enrollment growth by managing inquiries and CRM follow-ups.
• Foster a positive staff culture through coaching and day-to-day support.
• Resolve parent concerns with professionalism and empathy.
• Coordinate community events and outreach to strengthen family engagement.
• Oversee vendor scheduling, supply orders, billing support, and general campus organization.

Skills

Leadership experience

Communication

Relationship-building

Operational management

Collaborative leadership

Customer service

Education

Director Qualified in Early Childhood Education

Tools

Salesforce

CRM software

Billing software

Job description

Guidepost Montessori is seeking an experienced Floating School Admin Independent Contractor to partner with the Head of School and lead daily operations across our U.S. campuses. Cover maternity leaves, support schools in transition, and fill leadership gaps with calm, experienced guidance.

The role focuses on problem-solving, staff coaching, family engagement, and maintaining smooth campus operations wherever you’re needed.