Preschool Principal

Chesterbrook Academy is a multi-location school group with campuses in Florida, Illinois, Maryland, North Carolina, New Jersey, Pennsylvania, South Carolina, and Virginia offering outstanding private education to preschool and elementary students. Our preschools offer the perfect balance of learning and play, while our elementary program provides a challenging and robust curriculum, innovative instruction, and a vibrant school community. A career with Chesterbrook offers opportunities in education, summer camps, before and after school programs, and regional management with the support of our parent company, Spring Education Group.

Chesterbrook Academy is seeking an experienced, collaborative, and student-centered Preschool Principal to lead the academic, operational, and cultural life of our school. This role provides overall leadership for instructional quality, staff performance, enrollment, family engagement, licensing compliance, and financial stewardship.

In this role, you will cultivate a safe, engaging, and enriching environment where young children can thrive. You will guide the successful implementation of the Spring Education Curriculum, coach and develop faculty and staff, strengthen relationships with families, and ensure that daily school operations reflect Chesterbrook Academy’s high standards.

This position is ideal for a visible and accountable school leader who combines sound educational judgment with strong operational acumen, a growth mindset, and a can-do approach to building a collaborative, high-performing school community.

• Medical, dental, and vision insurance
• Paid holidays and sick days
• 401(k) plan with company match
• Tuition discounts for your children
• Professional development opportunities
• Education reimbursement and partnerships

• Provide overall leadership for the preschool, including the instructional program, daily operations, school culture, and the student and family experience
• Lead the successful implementation of the Spring Education Curriculum and ensure developmentally appropriate, engaging, and high-quality learning experiences across classrooms
• Recruit, hire, onboard, coach, develop, evaluate, and retain qualified faculty and staff while establishing clear expectations and accountability for performance
• Observe classroom practice, provide actionable feedback, and support teachers in strengthening instruction, classroom management, family communication, and professional growth
• Foster a collaborative, inclusive, and positive workplace culture in which employees feel supported, valued, and responsible for shared school goals
• Ensure a safe, clean, organized, and attractive school environment that supports learning and meets all health, safety, and operational expectations
• Maintain compliance with applicable state and federal laws, childcare licensing requirements, accreditation standards, company policies, and required recordkeeping practices
• Oversee staffing plans, scheduling, student supervision, emergency preparedness, and other daily operational processes necessary for a well-run preschool
• Manage the school’s budget, profit and loss performance, purchasing, resource allocation, and financial controls in partnership with regional and organizational leadership
• Drive enrollment growth and retention by partnering with admissions and marketing teams, engaging prospective families, supporting tours and events, and delivering an exceptional family experience
• Build trusted relationships with current families through proactive, professional communication and timely, thoughtful resolution of questions or concerns
• Develop strong relationships with community partners and represent Chesterbrook Academy through outreach, school events, and community engagement initiatives
• Partner with other Chesterbrook Academy leaders to support continuity of care, student transitions, shared best practices, and a cohesive educational experience
• Use enrollment, staffing, financial, operational, and student data to identify priorities, make informed decisions, and continuously strengthen school performance
• Model professionalism, sound…