Her first stage performance came in a North Denver bar called Ziggie's Saloon (near the Oriental Theater).

Her first album was a self-released, self-titled record called Sera Cahoone, which was praised by indie-rock radio station KEXP along with NPR.

[6] Seattle indie newspaper The Stranger called Sera's debut "a breathtaking collection of sad and dusky songs that reveal an artist of remarkable depth as well as a truly stunning voice.

"[7] In 2007, Cahoone was signed to the Seattle label Sub Pop Records[8] which was home to former Carissa's Wierd bandmates Ben Bridwell (Band of Horses) and later Mat Brooke (Grand Archives).

Askew brought together key Portland musicians like Rob Burger (Iron and Wine, Lucinda Williams), Dave Depper (Death Cab For Cutie) and Annalisa Tornfelt (Black Prairie) with Cahoone's Seattle bandmates – Jeff Fielder (Mark Lanegan, Amy Ray) and Jason Kardong (Son Volt, Jay Farrar).

Cahoone has toured with Son Volt, Matt Costa, Band of Horses, Grand Archives, Sea Wolf, Patrick Park, Tift Merritt, Beachwood Sparks, Fruit Bats, Ben Gibbard, Jay Farrar, Gregory Alan Isakov, Blitzen Trapper, Mason Jennings, Kathleen Edwards, and Joe Pug.

Sera Cahoone, and bandmate, Jason Kardong, were the first people to ever play music on the rooftop of Seattle's iconic Space Needle as part of the Sub Pop Records Silver Jubilee Celebration on July 11, 2013.