Assistant Head of School & Montessori Leader

Socket.dev; Chicago (IL); Hybrid; USD 80,000 - 105,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Paid time off and holidays

Tuition discount for two children

Job summary

Guidepost Montessori is hiring an experienced leader for our Chicago, IL campus as Assistant Director (Assistant Head of School). The role partners with the Head of School to ensure a high-quality learning experience and exceptional service to families.

You will build community, host outreach events, lead tours for new families, and manage enrollment while supervising daily school operations including billing and maintenance. Strong communication and organization are essential.

Qualifications

• DCFS requirements and regulatory knowledge for early childhood education leadership.
• Experience leading preschool or early childhood programs.
• Strong written and verbal communication skills.
• Excellent organizational and problem-solving abilities.
• Comfort with computer systems and enrollment management.

Responsibilities

• Support the Head of School to ensure high-quality learning experiences.
• Build a strong campus culture aligned with the organization’s mission.
• Plan and host community outreach events and tours for prospective families.
• Drive enrollment by managing leads and CRM activities.
• Oversee day-to-day operations: billing, supplies, scheduling, and maintenance.
• Engage with parents to foster community and address concerns.

Skills

Leadership

Community outreach

Communication

Organization

Education

Montessori certification

Tools

Salesforce/CRM

Billing software

Job description

Guidepost Montessori is hiring an experienced leader for our Chicago, IL campus as Assistant Director (Assistant Head of School). The role partners with the Head of School to ensure a high-quality learning experience and exceptional service to families.

You will build community, host outreach events, lead tours for new families, and manage enrollment while supervising daily school operations including billing and maintenance. Strong communication and organization are essential.