Jann cut her debut single under the name Jann Richards when she was 17.
In her twenties, Jann worked the western Canada lounge circuit and busked on city street corners.
In 1987 Jann signed with former Ian Tyson manager Neil MacGonigill when she was making ends meet by managing her parents' video store in Springbank.
In 1991 Jann signed with A&M/Island/Motown Records of Canada and recorded her debut album, Time for Mercy in 1993.
The 11 songs on that album included “I Just Don't Love You Anymore,” written by Jann in 1982, and "I Would Die for You" which quickly earned national attention.
Jann earned her first Juno Award in March 1994 as most promising solo performer. Jann's career continued to take off in Canada. She is one of the country's most popular and beloved singer-song-writers. By 2010 Jann had received eight Juno awards.