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Kevin O'Mara has a diverse work experience spanning various roles and positions. Kevin currently serves as a Leadership Coach at Instructional Empowerment, where they focus on empowering K-12 students to achieve grade level proficiency and upward mobility. Prior to this, Kevin worked as the President of School Exec Connect, where they provided leadership and guidance. Kevin also served as a Professor at Concordia University Chicago and as a Superintendent at Argo Community High School. Earlier in their career, Kevin held the position of Principal at Ridgewood High School.

Kevin O'Mara completed their high school education from St. Ignatius between the years 1972 and 1976. Kevin subsequently pursued higher education at Concordia University Chicago, where they obtained an Ed.D. in School Leadership from 2002 to 2008.