Assistant Head of School - Montessori Leader & Builder

Guidepost Montessori; Chicago (IL); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Mentor network

Career growth

Health/dental/vision insurance

Paid time off

75% tuition discount for two children

Meaningful education program

Job summary

Guidepost Montessori in Chicago seeks an experienced leader to join as Assistant Head of School. You will work closely with the Head of School to ensure a high‑quality learning experience for children, outstanding parent service, and a supportive, collaborative team culture across the campus.

The role emphasizes community outreach, tours for prospective families, and driving enrollment through a CRM. You will oversee day‑to‑day operations—billing, supplies, scheduling—and engage with parents to

Qualifications

• DCFS requirements
• Early childhood education leadership experience
• Affinity for connecting with people
• Strong organizational skills
• Exceptional written and verbal communication skills
• Strong attention to detail with a focus on results
• Facility with computer systems
• High degree of personal initiative

Responsibilities

• Support the creation of a strong campus culture aligned with the mission.
• Plan and host community outreach events.
• Give tours to prospective families and convert leads to enrolled families.
• Drive enrollment using a CRM system.
• Manage day-to-day operations: billing, supplies, scheduling maintenance.
• Interface with parents to build community and address concerns.

Skills

Leadership experience

Communication skills

Organizational skills

Attention to detail

Initiative

Computer literacy

CRM familiarity

Education

Montessori certification

Tools

Salesforce

Billing software

Job description

Guidepost Montessori in Chicago seeks an experienced leader to join as Assistant Head of School. You will work closely with the Head of School to ensure a high‑quality learning experience for children, outstanding parent service, and a supportive, collaborative team culture across the campus.

The role emphasizes community outreach, tours for prospective families, and driving enrollment through a CRM. You will oversee day‑to‑day operations—billing, supplies, scheduling—and engage with parents to