[2][3] Randy Dunn began his career as a fourth-grade elementary teacher at Gibson City, Illinois Grade School, where he worked from 1980 to 1983.

In Dunn's first move as superintendent, he hired two high level employees, a new budget director and a new general counsel, who had been pre-selected for the positions by the Blagojevich administration.

In August 2005, the Illinois State Board of Education made Dunn's appointment permanent, by removing "interim" from his title and extending his contract through January 2007.

The Murray State board of regents approved Dunn's hiring by a 7–4 vote during a special meeting in May 2006.

The campaign raised $71.73 million to benefit student scholarship endowments, support athletics, purchase new research and laboratory equipment, and advance campus improvements.

In October of that year, the UT presidential search panel announced that Randy Dunn was not among the finalists for the position.

As such, I have come to the conclusion that—even if I were to be chosen to be Missouri State's next president—the level of support necessary as an external candidate to guide that institution into a bold and dynamic future would be lacking."

He then expressed his intent to remain at Murray State; however, less than two months later he applied and was named as one of three finalists for the position of Florida Education Commissioner.

A report reviewed by board of regents members prior to the vote indicated that the university's academic standing had fallen since Dunn took over leadership, and enrollment at most of the regional campuses had fallen while enrollment at the main campus remained relatively flat during his tenure as president.

In the second vote, the board of regents upheld their original 7-4 decision to let Randy Dunn's contract expire.

Under the contract, Dunn would earn $375,000 per year for three years and receive benefits including health care, term life insurance, disability insurance, residence in the newly remodeled Pollock House, an American-made car, and membership at a local country club and one civic club.

Before his resignation, members of the Youngstown State University Board of Trustees, including its chair Dr. Sudershan Garg, indicated surprise when the news broke on February 16.

Jim Tressel was announced as the next President of Youngstown State University to replace Dr. Randy Dunn.

As a result, Dunn was ordered to vacate the university's presidency on March 21 and move out of the presidential residence by April 20.

Dunn formally submitted his application for the presidency on January 10, and he interviewed with the SIU board on February 12 in St. Louis.

[42][43] The University Board of Trustees called a special meeting that was held June 21, 2018, to discuss Dunn's future employment as president.

[47] In May 2019, a report was released from the Executive Ethics Commission of the State of Illinois in which it was determined that Dunn was responsible for two incidences of improper hiring.

The report also determined Dunn had abused search waivers while hiring his long-time friend and colleague Brad Colwell to the position of vice-president for student and academic affairs.

In April 2019, it was reported that Colwell had stepped down from his role as VP of student and academic affairs due to the investigation into his hiring.