He began his radio career at WMAX in Grand Rapids, Michigan as a news anchor and reporter. He also covered high-school football and basketball. He moved to competitor WCUZ in 1982, where he would cover sports for the next six years. Dickerson moved to Detroit in 1988 and WWJ, where he served as a general assignment news reporter and weekend news and sports anchor. He also hosted the post-game call-in show for the station's Detroit Lions broadcasts.

In 1995, Dickerson moved to crosstown competitor WJR, where he held a variety of positions. He served as co-host of the weeknight sports call-in show Sportswrap; morning sports anchor; sideline reporter and fill-in play-by-play announcer for Michigan Wolverines football; and play-by-play announcer for Michigan basketball for two seasons.

While visiting with legendary Tigers announcer Ernie Harwell in the WJR booth during the final game at Tiger Stadium in 1999, Dickerson was invited by Harwell to call an inning of play-by-play. The following season, he joined the Tigers' radio broadcast team full-time, calling the middle innings of each game while Harwell handled the rest. Along with former Tigers catcher and color analyst Jim Price, this crew remained intact for three full seasons, even as the team switched radio flagship stations (from WJR to WXYT) at the end of the 2000 season.

Dickerson took over as lead play-by-play announcer on Tigers radio following Harwell's retirement at the end of the 2002 season, working with Price as a two-man crew. Dickerson has called several events for Fox Sports Detroit television, including high school football since 2002, a Michigan State Spartans hockey game in 2008, and Detroit Titans basketball games in 2010 and 2011.

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