Apple Executive Who Launched Apple Pay Is Retiring After 25 Years

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. Her exit is one of several senior departures ahead of Tim Cook handing the chief executive job to John Ternus on September 1.

Jennifer Bailey, who has run Apple Pay since the service launched in 2014, is retiring in October after more than 25 years at Apple. Services chief Eddy Cue announced her departure in a staff memo seen by Bloomberg News. A successor will be named before she goes.

“Under Jennifer’s leadership, Apple Pay has changed the way hundreds of millions of our users pay,” Cue wrote. Bailey will stay on in an advisory role through the handover. Apple declined to comment.

The division she leaves behind is one of Apple’s most profitable. Apple Pay brings in more than $7.5bn a year on analyst estimates compiled by Bloomberg, and functions as a reason for customers to stay on iPhone. Bailey also built Wallet, which began as a place to store card details and now holds keys for homes, cars and hotels, along with identification.

Apple Card and the company’s recently announced device upgrade subscription both grew out of the same division. Before Apple Pay, Bailey ran Apple’s online store, having joined in the early 2000s from a string of internet companies.

People familiar with the move describe her exit as a significant loss, and as a sign of what is coming. Apple has a demographic problem. A cohort of executives who grew wealthy over decades at the company are reaching retirement age together, and no longer need to work.

General counsel Kate Adams is retiring this year, and environment chief Lisa Jackson left at the start of 2026. Former finance chief Luca Maestri and marketing veteran Phil Schiller have stayed on in smaller roles but are probably near the end. Cue, retail boss Deirdre O’Brien and marketing head Greg Joswiak have each been at Apple for around four decades.

The largest change lands on September 1, when Tim Cook hands the chief executive job to John Ternus and becomes executive chairman. Ternus, 51, who built Apple’s hardware for more than two decades, is expected to make further personnel changes and has already brought a retired hardware leader onto his team.

The drain is not limited to the executive floor. Apple’s design studio has lost nearly every Ive-era designer, a gap Ternus has said he intends to close.

Josh Rosenstock, a senior director of corporate communications, is also leaving, in what Bloomberg reports is an unrelated move.