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Assistant Head of School

Premier Early Childhood Education Partners
Chesapeake, VA Full Time
POSTED ON 5/14/2026
AVAILABLE BEFORE 6/12/2026
Description

Chesapeake Montessoriis seeking an energetic and passionate Assistant Head of School for our early childhood education and school age program!

To be QUALIFIED for this position, we require the following qualifications: previous work experience in a Montessori school is a MUST; previous leadership and/or administrative experience is preferred as well as an associate degre above or higher.

Required Shift: As the leader of the building, the Assistant Head of School must be able to meet the needs of the business which requires a flexible schedule to accommodate day-to-day operations, emergent situations, as well as afterhours family and community events.

Compensation: $22-25 per hour, based on experience and education

We are a family-oriented, close-knit organization and we have a lot to offer our next team member including:

  • 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 - we love to show appreciation for our teachers!

Our Hiring Process:

  • Resume screen
  • Phone screen with Recruiter (30 minutes)
  • Interview with Head of School (45 minutes)
  • Interview with Regional Director (45 minutes)
  • Offer

Main Job Responsibilities:

  • Assures that the curricular scope and sequence, as well as instructional strategies, reflect the school’s philosophy and goals. The Head of School provides leadership in the process of curriculum development.
  • 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.
  • 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.
  • Carry out the daily responsibilities of the classroom relating to the care of the children.

If you have a positive attitude, love working with children and desire to work in a fun and professional environment, we encourage you to apply today!

Chesapeake Montessori is an Equal Opportunity Employer. We embrace and celebrate diversity and inclusivity. We do not tolerate any kind of discrimination in our hiring processes against any groups protected by federal, state, or local law.

Salary : $22 - $25

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