Webb started his career in 1989 at Radio Wyvern in Worcester where he presented the evening show. From there he briefly presented the late night show at Severn Sound in Gloucester and then moved to MFM 103.4 to present evenings again. In 1991 he moved to Bradford to work at the newly re-launched Pulse of West Yorkshire. He hosted various shows until he took over presenting duties for Breakfast with co-host Debbie Lindley until his departure in 1996. More early starts followed with his move to Galaxy 101 in Bristol which had recently been acquired by Chrysalis Radio. As part of a major revamp for the station Webb hosted the Breakfast Show with Sally Bailey until March 1997.
In April 1997 Webb moved to BRMB, Birmingham to present the evening show and provide holiday cover for the then Breakfast host, Les Ross. It was during one of these cover periods in 1999 that Webb hosted the notorious Two Strangers and a Wedding contest where couples competed to win the chance to marry a complete stranger. Carla Germaine and Greg Cordell were the chosen couple who tied the knot having met only minutes before. The contest received condemnation from many but generated worldwide publicity for the station. It was later the subject of two networked ITV documentaries and acres of press coverage. Webb eventually took over the Breakfast Show full-time following the departure of Les Ross in 2002. The show went on to win several awards and was back in the media spotlight in 2006 with a second Two Strangers and a Wedding contest this time marrying Rebecca Duffy and Craig Cooper. Later in the same year a string of emails to the show from an anonymous female listener culminated in the sender hiring a giant billboard in Birmingham city centre to dump her husband whom she suspected of cheating. After twelve years, Webb was axed from BRMB in October 2009 following the purchase of the station by new owners Orion Media.
In 2003 Webb covered presenting duties for the nationally broadcast chart show Hit40UK. He has also presented the Capital FM produced and networked weekly entertainment show Seven and the Capital FM weekend Breakfast Show.
Webb has presented and contributed to a wide variety of TV shows throughout his career. These include regional news bulletins for Yorkshire Television's Calendar, “Two Strangers and a Wedding” documentaries for ITV, “The Home Health Show” for Discovery Home and Health, “The Last Word” for ITV Central and the weekly studio debate show “Central Extra” also for ITV Central.
Flaps Podcast
Along with former BRMB producer Mark Newman, Webb is a presenter and producer of the award-winning Flaps Podcast which discusses topics of interest to private and general aviation pilots. He is also a holder of a private pilot licence.