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Cheryl Dearing has a strong background in education, with several roles that showcase their expertise and leadership abilities. Cheryl began their career in 1998 as a Special Education Teacher at the Livingston County Special Services Unit, where they taught and managed a caseload of Junior High-aged students. In 2002, they joined Pontiac School District #429 as a Teacher, specializing in special education classes for 6th through 8th grade students. During their time there, they developed a program for self-contained ED/BD students and taught all academic subjects, including social skills. In 2007, they transitioned to the role of Dean of Students at Pontiac Junior High School, where they handled discipline issues, truancy, and assisted with administrative duties. In 2008, they became the Special Education Director for Pontiac Elementary School District #429, overseeing special education programs for approximately 300 students across four school buildings. Cheryl also managed state-funded grants and programs, such as the PreSchool for All program. In 2019, they served as the Principal at the Champaign Early Childhood Center in the Champaign Unit #4 District, a state-funded Preschool for All program catering to 360 3-5 year old children. Currently, Cheryl Dearing is the Assistant Director of Special Education at Champaign Unit 4 Schools, showcasing their dedication to supporting students with special needs at both the early childhood and elementary levels.

Cheryl Dearing's education history includes obtaining a Master's of Educational Leadership with a Type 75 Certification from Concordia University Chicago between the years 2005 and 2007. Prior to that, they earned a Bachelor of Education (B.Ed.) in Special Education from Illinois State University from 1995 to 1998. In their earlier years, they attended Eastern Illinois University from 1986 to 1990, studying Psychology and Education, although no degree was mentioned. Cheryl completed their high school education at Pontiac Township High School, where they received a High School Diploma.