Principal - Oakwood

Principal – Circle Academy, Oakwood, IL

Circle Academy in Oakwood, IL is seeking a dedicated and experienced Principal to lead our K–12 therapeutic day school. This is an exciting opportunity to lead a new school and help shape its culture, programs, and long-term vision. Join our team and help empower students with emotional and behavioral challenges to achieve success in school, at home, and in the community.

About Us

Cunningham is a leading child welfare and educational services agency, providing compassionate support and therapeutic interventions to over 953 children, youth, young adults, and families each year. Our comprehensive programs include residential treatment, special education, and community-based services. Circle Academy Oakwood, one of Cunningham’s private therapeutic special education schools, serves students in grades K–12. We offer a structured, nurturing, and therapeutic learning environment that promotes both academic and emotional growth, with a mission to prepare and empower students for meaningful success in all areas of life.

Position Overview

Reporting to the Director of Education, the Principal will:

• Oversee programmatic approaches and interventions with students


• Supervise curriculum, instruction, and academic/behavioral progress


• Manage special education programming and services


• Lead extracurricular activities and foster stakeholder relationships


• Provide supervision to the leadership team and school staff


• Maintain administrative oversight of school operations

Qualifications

• Required: ISBE Type 75 Administrative License; valid Illinois driver’s license


• Preferred:




• 3+ years of supervisory experience


• 5+ years working with youth with severe emotional or behavioral challenges


• LBS I and/or LBS II certification

Note: All prospective employees must complete a pre-employment physical and background check.

What We Offer:

• Competitive salary based on education and experience ($55,637 - $105,955 per year).


• Small class sizes: 10 or fewer students per class.


• Additional support staff: Two additional support staff (Paraeducator and Teaching Assistant) in every classroom.


• Relocation Assistance: Available up to $5,000.


• Summer Income: Opportunity to earn additional income over the summer (31 days at $35/hour).


• Additionally, Cunningham Children's Home is a qualified employer under the Public Student Loan Forgiveness (PSLF) program.

Benefits

• Medical, Dental, and Vision Insurance


• Life Insurance


• Paid Holidays and Leave


• Garner Health & Paytient Card — healthcare navigation and cost savings benefits


• Flexible Spending Account (FSA) & Dependent Care Account (DCA)


• Accident, Short-Term Disability, and Critical Illness Insurance


• 401(k) Retirement Plan with up to 6% Company Match


• Employee Assistance Program (EAP)


• Wellness Program


• Relocation Assistance


• Employee Referral Program

Why Join Us?

We offer a supportive work environment with opportunities for professional growth and personal fulfillment. Our culture is grounded in spirituality, teamwork, integrity, and respect. Salary is competitive and based on education and experience. Cunningham Children’s Home is an Equal Opportunity Employer.

Cunningham and the Community: 
Urbana is part of the twin cities of Champaign–Urbana  in east-central Illinois, about 140 miles south of Chicago, 125 miles west of Indianapolis, and 170 miles northeast of St. Louis. Home to the University of Illinois Urbana-Champaign, the area combines the energy of a college town with the warmth of a close-knit community. Residents enjoy diverse dining, parks, festivals, and a rich cultural scene—making it an ideal place to live, work, and grow.

Founded in 1895, Cunningham Children’s Home is a leading child welfare and educational services agency, supporting more than 977 youth and families each year through residential treatment, special education, and community-based programs.