Jennifer Bailey, head of Apple Pay and Wallet since the service launched in 2014, is retiring in October after more than 25 years at Apple. Jennifer Bailey, who has run Apple Pay since the service launched in 2014, is retiring in October after more than 25 years at Apple. “Under Jennifer’s leadership, Apple Pay has changed the way hundreds of millions of our users pay,” Cue wrote. Before Apple Pay, Bailey ran Apple’s online store, having joined in the early 2000s from a string of internet companies. The largest change lands on September 1, when Tim Cook hands the chief executive job to John Ternus and becomes executive chairman.