Sheard was classically trained at the Royal Conservatory of Music, but cites Joni Mitchell, Rheostatics and Ron Sexsmith among the influences that led her to pop music. Her style is often compared to artists such as Jane Siberry, Mary Margaret O'Hara and Tori Amos.
She is the sister of novelist Sarah Sheard and pianist John Sheard, and the great-great-granddaughter of Joseph Sheard, a former Mayor of Toronto. She married record producer Michael Phillip Wojewoda in 1999; Sheard and Wojewoda divorced two years later.
Sheard is best known for her cover of Veal's "Mexico, Texaco" on her Reptilian album; the video was directed by her for MTV Canada. Sheard has received critical acclaim in both Canada and the US.