Cleveland is the son of former Samford University dean of admissions Tom Cleveland. He grew up in Homewood, attending Shades Cahaba Elementary School, Homewood Middle School, and graduating from Homewood High School in 1985. He went on to earn his bachelor's degree in Secondary Education at Samford, his master's in Secondary Education and Education Specialist Degree in Administration at the University of Montevallo, and his doctoral degree at Samford.
After a short time as a youth minister at Auburn University, Cleveland began his academic career as a social studies teacher and coach at Minor High School (1991 - 92), then moved to Bottenfield Junior High School, where he stayed for six years.
He returned to Minor to become assistant principal in 1998. In 2001, he became assistant principal of Spain Park High School in Hoover. He was hired as principal of Homewood Middle School in 2004. He served there until he applied and was accepted for the position of Homewood City School's assistant superintendent for business operations in 2007. He was promoted in April 2008 to succeed superintendent Jodi Newton at her retirement in July of that year.
|Homewood Middle Principal
|Homewood City Schools Superintendent
- "Cleveland Leaves Spain Park To Lead Homewood Middle." (June 30, 2004) The Birmingham News
- "Principal Retains His Connection To System." (August 4, 2004) The Birmingham News
- Bryan, Kim (April 19, 2007) "Principal moves to business side." The Birmingham News
- Bryan, Kim (April 29, 2008) "Homewood school board picks Bill Cleveland as new superintendent." The Birmingham News
- Bryan, Kim (August 11, 2008) "Homewood school system chief is first product of Homewood schools at job." 'The Birmingham News
- "Homewood City Schools Announces Cleveland as Superintendent." (August 2008). The Homewood Times, p. 11