Preschool Assistant Principal

Company: Chesterbrook Academy
Location: Wheaton
Posted on: January 7, 2026

Job Description:

Spring Education Group’s Early Childhood Education Division includes nearly 150 schools offering services from infant care through Pre-K/K programs, as well as summer camp and after-school programs . Our locations span a nationwide geographic footprint and a diverse array of pedagogical approaches — including our proprietary Links to Learning curriculum that draws from the collective expertise of renowned early-age educators such as Dewey, Piaget and Vygotsky; Montessori schools that embrace both accredited Montessori methods – AMI (Association Montessori Internationale ) and AMS (American Montessori Society); and progressive language immersion programs in Mandarin and Spanish. Chesterbrook Academy is seeking a dedicated and inspiring Assistant Principal who is passionate about early childhood education and eager to grow into a future school leadership role. This is a hands-on leadership position where you’ll play a vital role in supporting our school’s daily operations, mentoring teachers, and ensuring a positive experience for students and families. Our Assistant Principals lead by example—balancing time in the classroom with administrative responsibilities, and always modeling our school values of care, excellence, and collaboration. What You’ll Do Support the Principal in all aspects of school operations, including staffing, family communication, and compliance. Serve as the on-site leader when Principal is out covering all aspects of the business. Partner with teachers to strengthen classroom quality and curriculum delivery. Step into the classroom as needed to support instructional coverage or special projects. Foster a warm, inclusive culture that inspires both children and staff to thrive. Participate in leadership development to prepare for future advancement into a Principal role . Qualifications Must be at least 21 years of age and meet state licensing requirements. Degree in Early Childhood Education, Child Development, or related field preferred. Minimum 2–3 years of experience in a licensed childcare or early education setting. Strong communication, organization, and relationship-building skills. A collaborative, solutions-focused mindset and genuine passion for developing others. Authorization to work in the United States Why Join Chesterbrook Academy Career pathway toward Principal and higher leadership opportunities. Competitive pay, full benefits, and professional development support. A people-first culture grounded in teamwork, respect, and growth. The opportunity to make a lasting impact in children’s lives while helping shape the next generation of educators. If you’re ready to take the next step in your leadership journey and help us continue developing the best schools and educators in America — apply today! To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions. In general, this position requires an individual to frequently walk, stand, sit, squat, stoop, reach, kneel, rise from the floor, twist, listen, read, write, and speak the English language. In addition, this position often requires an individual to carry, lift, use repetitive or fine hand movements, and occasionally push, pull, or bend. This position is regularly required to hear and use clear vision with or without correction. Spring Education Group, including, but not limited to SEG Inc., and their affiliates (collectively “Company”) is an Equal Opportunity Employer. All qualified applicants for employment and employees are provided equal employment opportunities, including in recruitment, hiring, and assignment, without regard to actual or perceived race, color, religion and religious creed, sex (including pregnancy and related conditions), sexual orientation, gender identity, gender expression, marital or familial status, age, national origin, ancestry, disability, genetic information, military/veteran status, or any other classification protected by federal, state, or local law. The Company expressly prohibits any form of unlawful employee or student harassment or discrimination.

Keywords: Chesterbrook Academy, Orland Park , Preschool Assistant Principal, Education / Teaching , Wheaton, Illinois