Whitters released her debut full-length album in 2015 titled Black Sheep. Whitters co-wrote Little Big Town's song "Happy People", from their 2017 album The Breaker. On September 13, 2019, Whitters released an Extended play entitled "The Days", which serves as the first half of her upcoming album, "The Dream". On January 24, 2020, Whitters released a single called "Janice at the Hotel Bar", written with her frequent collaborator Lori McKenna. In June 2020, Whitters signed with Big Loud Records’ imprint Songs & Daughters.
