Scarlett High School, Andrews studied music and dance, where she also co-hosted pep rallies with eventual singer Jocelyn Alice.
[7][8] Andrews was discovered by Chris Smith, the manager of Nelly Furtado and Alessia Cara, after hearing her song "Adore" on MySpace in 2005.
[5][7][10] She released her debut single "Tumblin' Down" in 2010, which was featured on the sixth season of American medical drama television series Grey's Anatomy.
[12] She also released another EP exclusively on Rap-Up titled SexTape on 9 May 2013, which contained covers of songs including Usher's "Climax" (2012), The-Dream's "Rockin' That Shit" (2008), and Jeremih's "Birthday Sex" (2009).
[3] Andrews first encountered then 14 year old Lennon Stella on the set of 2012 television series Nashville, where she found her passion for developing young artists.
[28][29] In 2023 she started a new publishing venture, “Jennasis music” alongside her partner Stephen Kirk, “Sixteen sound”, in partnership with Warner Chappell.
[30] She has been influenced by a range of artists including Donny Hathaway, Billie Holiday, Aaliyah, Massive Attack, Portishead,[12] Carly Simon, and Carole King.
[13] During the COVID-19 pandemic in 2020, Andrews began hosting a web series titled The Green Room, which appears on Dash Radio and is produced in partnership with The Jed Foundation and She Is The Music.