Taylor started working with the Spears family when Jamie Lynn Spears got pregnant at the age of 16, according to Page Six. However, it was January 2008 when Taylor first appeared on Today as the Spears family spokesperson, speaking on behalf of Britney.
Lynne Spears, Britney's mother, wrote in her 2008 memoir, "Through the Storm," that Taylor and Britney's father, James "Jamie" Spears, had a discussion shortly after this about putting Britney under a conservatorship. "Jamie was going to file for the conservatorship on January 22 . . . but he and his business manager, Lou, felt God leading them to wait, fast and pray, despite the frustration of a phalanx of lawyers," Lynne wrote, according to Page Six.
Taylor abruptly stepped down as Britney's business manager in November 2020.