According to CMT, Hailey Whitters and singer-songwriter Lori McKenna caught the attention of Little Big Town in 2016. They had written a song called "Happy People" one year prior, an uplifting melody about having a good outlook on life and finding the good in others. Little Big Town caught wind of the song, and liked it so much that they asked if they could put it on their 2017 album, "The Breaker." The band released "Happy People" as the first single of the album, which opened huge doors for Whitters.

"@littlebigtown gave me my first single at country radio as a songwriter back in 2017 with 'Happy People' ... I saved up all those royalty checks to self-fund my record, 'The Dream,'" Whitters wrote in an Instagram post from December 2020. "They're a big part of my story and one of the main reasons I get to say today that I feel like I'm #livingthedream." Whitters later joined Little Big Town on tour, forming a long-term friendship and business partnership with the band, via Sounds Like Nashville. So, by the time the artists released "Fillin' My Cup," Whitters was already a force to be reckoned with.