Early Childhood Head of School at Kensington School in Chicago, IL

Kensington School, a premier private preschool with over 55 years of excellence in Early Childhood Education, is seeking a dedicated and experienced Head of School to join our leadership team. This full-time leadership role offers a unique opportunity to grow within a rapidly expanding, family-led organization that prioritizes children, families, and staff.

At Kensington School, our school leaders are empowered to focus entirely on the school experience—building meaningful relationships with children, families, and staff. With robust support from our Home Office in areas such as Admissions, Payroll, Hiring, Curriculum, Maintenance, Publishing, IT, Purchasing and Food Services, our school leaders are free to focus on what truly matters: people.

Join a team of qualified, experienced professionals dedicated to delivering excellence in Early Childhood Education. As a Head of School, you’ll have the resources and inspiration to bring big ideas to life—all within our purposeful and beautiful environments designed exclusively for Kensington School by our in-house architect.

Our leaders cultivate a collaborative and joyful community. We celebrate one another throughout the year with staff events, and we make a difference through meaningful monthly charity initiatives.

Compensation & Benefits

• Our Head of School earns a salary of $75,000 to $90,000 annually.

  • Extraordinary bonus opportunities.

• Medical, Dental, and Vision insurance

• 401(k)

• Paid Time Off

• Paid CPR/First Aid certification

• Access to a professional career coach

• This is a full time position.

Qualifications

• Must meet or exceed DCFS Director requirements
• Prior leadership and administrative experience in a licensed childcare facility
• Strong problem-solving skills and a creative, solutions-oriented mindset
• A genuine passion for Early Childhood Education is essential

Build your career at Kensington School—a trusted, family-led organization dedicated to creating exceptional early learning experiences.

✨ Learn more about our philosophy and programs at https://www.kensingtonschool.com