Raised in the continental southeast by musical parents, Siskind was exposed to bluegrass and old-timey music as a toddler, an experience that fueled her songwriting from an early age. She began writing music at 11 and completed her first album three years later. Regional songwriting competitions began to recognize her marriage of rustic Americana and contemporary country, and Siskind moved to Nashville at the age of 21, where she continued to release albums while attracting attention from industry veterans.

Bluegrass icon Alison Krauss recorded a version of Siskind's "Simple Love" in 2007, and the song's subsequent Grammy nomination helped raise the songwriter's profile even further. She subsequently contributed backing vocals to a Paul Brady album and toured Europe alongside Bon Iver, whose sets often concluded with a performance of her song "Lovin's for Fools." Meanwhile, Siskind also found time to continue writing music, and Say It Louder marked her sixth release in 2009. A reissue of her debut album, 2003's Covered, appeared in 2013. ~ Andrew Leahey