[1] Bennett began his career as a teacher of mathematics at Maitland Boys' High School in 1968.
He was appointed as Head of Mathematics at Dover Heights Girls' High School in 1978.
From 1986 Bennett held a variety of positions in assessment and information services with OBOS and its precursor.
[1] During his term as Chief Executive, Bennett oversaw the implementation of significant changes to the Higher School Certificate, including standards-referenced assessment and reporting,[2] onscreen marking of examinations,[3] a mandatory course in academic integrity[4] and the release of HSC results by SMS.
[5] In 2009 Bennett was awarded the Wyndham Medal by the Australian College of Educators for his leadership and intellectual contribution.