After graduation, West moved with her family to Cleveland, Ohio, where she began appearing on the television program "Landmark Jamboree" as one half of a country pop vocal duo called the "Kay-Dots" alongside partner Kathy Dee. At the same time, West made numerous trips to Nashville in the hopes of landing a recording deal. In 1959, Bill and she auditioned for producer Don Pierce at Starday, and were immediately offered a contract. The singles West cut for the label proved unsuccessful, but she moved to Nashville two years later, where her husband and she fell in with aspiring songwriters, including Willie Nelson, Roger Miller, Hank Cochran, and Harlan Howard. West often played hostess to these struggling songwriters, offering them a place to stay and eat. In return, they taught West about the structure of songwriting. During this time, she also became a close friend of groundbreaking female country singer Patsy Cline and her husband Charlie Dick.