Montessori School Leader - Enrollment & Community Growth

Guidepost Montessori; Chicago (IL); On-site; USD 50,000 - 60,000; Full time

Benefits offered by this job

Competitive salary 50k-60k USD

Health, dental, vision insurance

Paid time off & holidays

75% tuition discount for two children

Job summary

Guidepost Montessori in Downtown Chicago is seeking experienced School Leaders for future opportunities across our network. The role includes guiding campus teams, supporting enrollment health, fostering family relationships, and ensuring operational and program excellence.

Ideal candidates meet Illinois DCFS director requirements and have a background in early childhood education, school operations, admissions, or leadership.

Qualifications

• Meet Illinois DCFS director requirements.
• Experience in early childhood education, school operations, admissions, or leadership roles.
• Highly organized and able to manage multiple priorities effectively.
• Enjoy working with families and building strong relationships.
• Communicate clearly and professionally, both verbally and in writing.
• Strong attention to detail and follow-through.
• Comfortable using systems and learning new tools.
• Take initiative and are willing to step in where support is needed.

Responsibilities

• Supporting a strong, mission-aligned culture on campus that reflects our values.
• Building relationships with families and creating a welcoming, high-quality school experience.
• Leading tours for prospective families and guiding them through the enrollment journey.
• Managing the enrollment process, including lead tracking and follow-up through CRM systems.
• Planning and supporting community outreach events.
• Overseeing day-to-day school operations, including billing, supply ordering, and facilities coordination.
• Responding to family questions and resolving concerns with professionalism and care.
• Partnering with school and regional leaders to support overall school performance and consistency.

Job description

Guidepost Montessori in Downtown Chicago is seeking experienced School Leaders for future opportunities across our network. The role includes guiding campus teams, supporting enrollment health, fostering family relationships, and ensuring operational and program excellence.

Ideal candidates meet Illinois DCFS director requirements and have a background in early childhood education, school operations, admissions, or leadership.