Starting in Regina at CKCK-AM as announcer, he moved thru the ranks to the position  of General Manager of the station, and then was moved to the GM spot at Winnipeg’s CKRC-AM.

“You can’t actually be in radio, in my opinion, if you haven’t spent time in Winnipeg, Gary told Broadcast Dialogue in 2005. “It is the proving ground and the testing ground; it really makes people understand what radio is all about.”

His success at CKRC didn’t go unnoticed. In 1984, there came a phone call from Toronto, and Gary was off on the next rung up the ladder, as President of the Radio Bureau of Canada, where he spent three years assembling a team that organized the first national training program for radio sales people, and the first national sales managers’ conference in Canada.

His next move was in 1987, to Selkirk Communications Ltd. as Vice-President of Radio, with responsibility for stations located in Toronto and western Canada. When Rogers purchased Selkirk in 1989, Gary was on the move again, this time to Vancouver, where he was still in charge of those same radio stations, but where he also was to develop SRN – the Satellite Radio Network – which at its peak was sending programming via satellite, to 246 Canadian radio stations from coast to coast, and as such was perhaps the fore-runner to the 2005 version of Satellite Radio.

In 1994, Gary returned to Toronto to serve as Executive Vice President of Radio with a mandate to expand the Rogers group of stations. Once again he demonstrated a keen sense of the market, and launched several news-talk format stations, including Toronto’s highly successful CFTR.

In March of 2002, Gary was promoted to the position of CEO, Radio for Rogers Media, responsible for shepherding the operation of 46 stations. 

In 2006, Gary Miles was inducted into the CAB Broadcast Hall of Fame.