Floating School Admin

Location: Chicago, Illinois Bring your leadership experience to a school community where it will make an immediate impact. Guidepost Montessori is seeking an experienced educational leader to join our team as a Floating School Admin Independent Contractor. 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 role offers the flexibility to step in where you're needed most, covering campuses during maternity leave or other staffing gaps, and supporting schools across a region when the need arises, all while partnering with an experienced Head of School. About Guidepost Montessori 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. The Opportunity As the Floating School Admin, you'll serve as a trusted partner to the Head of School, stepping in to lead daily operations at campuses across the region, whether covering a leave, supporting a school in transition, or filling a temporary leadership gap. You'll ensure an exceptional experience for children, families, and staff wherever you're needed. 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 role where your judgment, professionalism, and ability to build relationships quickly will have an immediate impact. What You'll Do Partner with Heads of School to oversee daily campus operations, stepping in during maternity leave or other staffing needs across the region Build strong relationships with current and prospective families and guide them through school tours and the admissions process Support enrollment growth by managing inquiries and following up with prospective families in our CRM Foster a positive, collaborative staff culture through coaching and day-to-day support Resolve parent concerns with professionalism, empathy, and sound judgment Coordinate community events and outreach to strengthen family engagement Oversee operational needs such as vendor scheduling, supply orders, billing support, and general campus organization What We're Looking For Qualifications 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 Preferred Qualifications Director Qualified in Early Childhood Education 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 What We Offer The opportunity to make a meaningful impact without carrying sole responsibility for a campus A collaborative leadership partnership with an experienced Head of School Competitive pay of $24-30/hr The opportunity to support a mission-driven organization dedicated to transforming education If you're an experienced educational leader who still enjoys working with families, supporting educators, and helping schools succeed, we'd love to talk with you about joining our team. Guidepost Global Education and Guidepost Montessori are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation.