School Leadership

We are always looking to connect with experienced School Leaders across the Downtown Chicago area who are interested in future leadership opportunities within our Guidepost Montessori network!

School Leadership Opportunities:

We are looking to connect with experienced school leaders who share our passion for Montessori education and who have demonstrated success in building or supporting strong teams, cultivating thriving school communities, and ensuring high-quality educational experiences for children and families.

Depending on the specific opportunity, School Leaders within our network may be responsible for leading campus teams, supporting enrollment health, fostering family relationships, and ensuring operational and program excellence.

Responsibilities may include, but are not limited to:

• 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 key aspects of 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

What we offer:

• Ongoing professional development
• A network of supportive peers and mentors who regularly share best practices
• Career growth and promotion opportunities
• A competitive salary of $50,000 - $60,000
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% tuition discount for two children at any school within our network (we serve children 3 months through 6 years old)
• The opportunity to contribute to a high-quality educational program that serves the individual needs of each child

We'd love to talk with candidates who:

• Meet Illinois DCFS director requirements
• Have experience in early childhood education, school operations, admissions, or leadership roles
• Are 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
• Have strong attention to detail and follow-through
• Are comfortable using systems and learning new tools
• Take initiative and are willing to step in where support is needed

We'd prefer candidates who have:

• Experience in roles such as school leadership, admissions, program management, or operations
• Familiarity with the Montessori method of education or Montessori certification
• Experience using CRM systems and billing platforms
• Knowledge of the local community to support outreach and enrollment efforts