Hailey Whitters started her musical career in Nashville's songwriting community during the mid-2010s and emerged as an American country singer-songwriter from Shueyville Iowa, known for her heartfelt storytelling and roots-driven sound. The country singer-songwriter gained recognition through her ability to merge contemporary country music with traditional elements while delivering relatable lyrics and authentic vocal delivery.

Audiences first encountered her introspective small-town stories and authentic country music through her debut album Black Sheep in 2015. She established herself as a respected songwriter before her sophomore album The Dream (2020) brought her mainstream success with hits "Ten Year Town" and "Fillin' My Cup." The tracks demonstrated her skill at writing strong anthems about everyday life that stem from genuine emotional experiences.