Assistant Head of School

Chesapeake MontessoriChesapeake, VA
Onsite

About The Position

Chesapeake Montessori is seeking an energetic and passionate Assistant Head of School for our early childhood education and school age program! This role requires a flexible schedule to accommodate day-to-day operations, emergent situations, and after-hours family and community events. The Assistant Head of School will be responsible for ensuring the school's philosophy and goals are reflected in the curriculum and instructional strategies, organizing activities and cultural experiences, and overseeing after-hours programs. This position also involves building strong relationships with parents, teachers, and children, managing enrollment, overseeing the budget, and managing staff hiring and training. Additionally, the role requires meeting state licensing requirements, directing staff and parent education, organizing admissions events, and fulfilling the physical demands of working with young children.

Requirements

  • Previous work experience in a Montessori school is a MUST
  • Associate degree or higher
  • Physical ability to work around small children including sitting, standing, walking, running, and climbing stairs.
  • Ability to lift and carry up to 40 lbs. and fulfill all physical requirements of the role.

Nice To Haves

  • Previous leadership and/or administrative experience

Responsibilities

  • Assures that the curricular scope and sequence, as well as instructional strategies, reflect the school’s philosophy and goals.
  • Organizes activities, elective offerings, and cultural experiences to round out the school’s academic program and provide for student interest development.
  • Establishes and oversees programs for after-hours including extended day and summer programs.
  • Builds and maintains a strong/positive relationship between parents, teachers and children through engagement events and on-going interaction.
  • Commitment to the growth of the school by consistently maintaining full enrollment.
  • Manages the budget along with thorough record keeping and payroll management.
  • Execute the hiring, training, and managing new staff.
  • Meets and maintains state licensing requirements and on-going compliance.
  • Directs continued education and professional development for all staff and the parent community.
  • Organizes admissions events for prospective/accepted students and families.
  • Carry out the daily responsibilities of the classroom relating to the care of the children.

Benefits

  • Competitive Pay
  • Paid Trainings, including Enhanced Career and Professional Development
  • Generous Benefits Package, including Dental, Medical, and Vision Insurance
  • 401k with Match
  • Discounts for Childcare
  • Fun and Positive Place to Work
  • Open Door Policy
  • Shirts and Swag
© 2026 Teal Labs, Inc
Privacy PolicyTerms of Service