Copy of Assistant Head of School (Assistant Director)

We're now hiring an experienced leader to join our founding team as we open a new school in the Wilton, Connecticut area!

 is a community of  educators who are driven by a deep desire to bring about widespread change in education today. We believe that the traditional method of education used in most schools is antiquated, outdated, and broken. To meet the needs of today's students and to bring about true progress in the world around us, we need an education model that fosters independence and develops competent, capable, action-oriented thinkers and change agents. To that end, we are committed to dramatically increasing the amount of high-fidelity, authentic Montessori programs, not only in the U.S., but around the globe! 

The Assistant Head of School Position:

The Assistant Head of School works closely with the Head of School to ensure that the school provides a high-quality learning experience for children, exceptional customer service to parents, and a supportive, collaborative work environment for staff. The ideal Assistant Head of School will love building community, working with parents, and leading community outreach initiatives. Key responsibilities include, but are not limited to:

• Supporting the creation of a strong culture on campus that embodies the mission of our organization
• Planning and hosting community outreach events
• Giving tours to prospective families, and converting leads to enrolled families
• Driving the enrollment process (managing leads utilizing a CRM system)
• Managing general, day-to-day operations for the school: billing, supply ordering, scheduling maintenance
• Interfacing with parents to build community, answer questions, and resolve any concerns that may arise

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
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 100% tuition discount for two children at any school within our network (we serve children 3 months through 12th grade)
• The opportunity to contribute to a high-quality educational program that serves the individual needs of each child

We'd love to talk to you if you possess:  

• A minimum of 12 college credits in Early Childhood Education or Child Development (CDA preferred)
• Early childhood education leadership experience
• An 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
• A high degree of personal initiative

Guidepost Montessori is a project of Higher Ground Education. You can learn more about our mission by visiting