[3] Born in Melbourne, Wailes was educated at Caulfield Grammar School, where he was active as a student musician, performing in a wide range of ensembles as a flautist and also as a singer in various church and community choirs.
Wailes continued practicing choral music in various choirs upon leaving school, and played in various amateur orchestras throughout his secondary and early university years.
[5] He has directed the choir in hundreds of performances, and in 2010 led it on its first international tour, conducting throughout Germany, Austria, Slovakia and the Czech Republic.
[citation needed] Wailes has also conducted the Box Hill Chorale (formerly the Box Hill Choral Society) since 1995, and has directed Faculty Choirs at the University of Melbourne, Melba Memorial Conservatorium of Music, and the School of Music Conservatorium at Monash University.
In 2019 he was the recipient of a Deakin Community Award, presented by Michael Sukkar MP and Susan Alberti AC.
Wailes has assisted Russian maestro Valery Gergiev as backstage conductor and extra chorus director for the Kirov Opera's performances for the Melbourne International Festival of the Arts, and has prepared and directed choirs for the Perth International Arts Festival's performance of Schoenberg's Gurre-Lieder with the Australian Youth Orchestra.