Born in Yorkshire, England, Iain started ballet at the age of 14 and moved to London at 16, where he trained for two years with The Rambert School of Ballet, a year at The Royal Ballet School and a further year as an apprentice with The Sadler's Wells Royal Ballet where he was offered a full time position. His main principal repertoire included Ashton's The Dream, The Two Pigeons, La Fille mal Gardee (Colas & Alain), Bintleys The Snow Queen, Fokine's Les Sylphides and Petrushka, Balanchine's The Prodigal Son, van Manen's Five Tangos, Coppelia and Swan Lake.
In 1989 he transferred to The Royal Ballet, Covent Garden, to perform character roles which included Bottom in Ashton's The Dream, The Small Sister, Dancing Master & Napoleon in Cinderella, and Mrs. Tiggy-Winkle and Pigling Bland in Tales of Beatrix Potter, MacMillan's The Doctor in Different Drummer and a Client in Manon and Sancho Panza in Baryshnikov's production of Don Quixote. In 1996, Webb retired from The Royal Ballet, but was invited back as a guest artist to give three farewell performances at Covent Garden as the Small Sister in Ashton's Cinderella. After retiring as a dancer, he was invited by Matthew Bourne to be Rehearsal Director for The West End, L.A. and Broadway seasons of Swan Lake and continued to work with Bourne on his production of Cinderella.
In 1999, Webb was asked by Tetsuya Kumakawa to join his newly formed K-Ballet Company in Japan as Ballet Master and two years later was appointed Assistant Director. During this time he also worked with many international stars including Adam Cooper, with whom he co-directed The Adam Cooper Company and organized their tour to The Kennedy Center. Likewise, he co-produced with Johan Kobborg the London performances of Out of Denmark and staged Roland Petit's Carmen Pas de Deux for Alessandra Ferri & Julio Bocca for American Ballet Theatre's 65th Anniversary Gala. Throughout Iain's career he has produced and directed many international performances which included presenting dancers from Royal Danish Ballet, Paris Opera Ballet, New York City Ballet and Stuttgart Ballet to name a few. He has been guest teacher for White Oak Project, Birmingham Royal Ballet, Rambert Dance Company, as well as teaching master classes and workshops for all the major ballet schools in England.
In July 2007, Webb took over the directorship of The Sarasota Ballet and during the last four seasons the company has performed 102 ballets & divertissements which include 16 world premieres, 55 Sarasota premieres, 4 new productions and 27 American premieres. These include ballets by: Ashton, de Valois', MacMillan, Balanchine, Cranko, Tudor, van Manen, Bourne, Wheeldon, Tharp and Tuckett. Under Webb's direction the company has received critical acclaim in The New York Times, The New York Financial Times, Sarasota Herald Tribune, St. Petersburgh Times, Orlando Sentinel, Dancing Times (London); He has developed a stronger financial foundation for the company, was selected to serve on the National Endowment for the Arts Dance Panel and recently signed a contract extending his tenure six more years.