Gillespie joins GMG Radio in April and will take on responsibility for all commercial activity for the group's portfolio of 13 Smooth, Real, Century and Rock Radio stations.
His role will include responsibility for marketing, national and regional sales, plus GMG Radio's digital activity.
Between 1998 and 2004 he was head of radio and, latterly, head of sponsorship and branded content at OMD UK, followed by the role of director at OPera Media.
His efforts within the commercial arena earned him a Radio Academy Fellowship in 2002, the first awarded to anyone from a media agency.
Gillespie's appointment comes as the current commercial director and deputy chief executive Stuart Taylor moves to take up the role of chief executive in April, following the departure of John Myers, who is leaving the group after 10 years.
On joining the group, Gillespie will report directly to the chief executive and will join the GMG Radio board.
Taylor said: "We are really pleased to welcome Jonathan to GMG Radio where his wide experience in radio, agencies and digital will strengthen an already formidable team."
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