Interim Assistant Director

Guidepost Montessori is seeking an experienced educational leader to join our team as an Interim Assistant Head of School. This is an ideal opportunity for a retired or seasoned school administrator who enjoys mentoring others, building relationships with families, and helping schools thrive without the demands of leading an entire campus independently.

This full-time leadership role provides maternity leave coverage and offers the opportunity to use your expertise to support a vibrant school community while working alongside an experienced Head of School.

At Guidepost Montessori, we believe children thrive when they're given the freedom, support, and environment to become confident, capable, and independent learners. Our mission is to expand access to authentic Montessori education by building exceptional schools where children, families, and educators flourish together.

With more than 60 schools across the United States, we're committed to providing high-quality educational experiences while creating welcoming communities for every family we serve.

As the Interim Assistant Head of School, you'll serve as a trusted partner to the Head of School, helping lead the daily operations of the campus while ensuring an exceptional experience for children, families, and staff.

We're looking for someone who enjoys solving problems, supporting teachers, connecting with parents, and bringing calm, experienced leadership to a busy school environment. This is a hands-on leadership position where your judgment, professionalism, and ability to build relationships will have an immediate impact.

• →Partner with the Head of School to oversee the daily operations of the campus.
• →Build strong relationships with current and prospective families through exceptional communication and customer service.
• →Conduct school tours and guide prospective families through the admissions and enrollment process.
• →Support enrollment growth by managing inquiries and following up with prospective families using our CRM system.
• →Help create a positive, collaborative culture for staff while coaching and supporting team members.
• →Resolve parent concerns with professionalism, empathy, and sound judgment.
• →Coordinate community events and outreach efforts to strengthen family engagement.
• →Oversee operational responsibilities including scheduling vendors, ordering supplies, billing support, and maintaining an organized campus.
• →Identify challenges, develop practical solutions, and help ensure the school operates smoothly each day.

• 24 ECE/Child Development units or Site Supervisor permit
• Previous leadership experience in an early childhood education or school setting.
• Experience as a School Director, Assistant Director, Principal, Program Director, or similar leadership role.
• A proven ability to lead confidently with minimal direction.
• Strong organizational and operational management skills.
• Excellent communication and relationship-building abilities.
• Experience supporting admissions, enrollment, or customer service.
• Comfortable using technology, CRM systems, and administrative software.
• A collaborative leadership style with a solutions-focused mindset.
• Passion for supporting children, educators, and families.

• Experience leading a preschool, Montessori, childcare, or private school.
• Familiarity with Montessori education.
• Experience with Salesforce or similar CRM platforms.
• Knowledge of billing or school management software.
• Strong connections within the local community or experience supporting community outreach initiatives.