Jennifer Bailey to retire after leading Apple Pay Services since launch

By Mark Gurman

 

Apple Inc.’s Jennifer Bailey, the longtime head of Pay and Wallet services, is retiring after more than two decades at the company, adding to a sweeping changing of the guard at the iPhone maker.

 

Apple services chief Eddy Cue announced her departure in a staff memo seen by Bloomberg News. Bailey, who has been vice president of Apple Pay since its launch in 2014, is exiting in October, he said.

 

“Under Jennifer’s leadership, Apple Pay has changed the way hundreds of millions of our users pay,” Cue said. “Before Jennifer’s transition at the end of October, we will announce our succession plan, and Jennifer will continue to be available to support the transition in an advisory role.”

 

A spokesperson for Cupertino, California-based Apple declined to comment.

 

Apple Pay, a payment service that lets people make purchases in person and online, has become one of the company’s most lucrative offerings. It generates revenue of more than $7.5 billion a year, according to analyst estimates compiled by Bloomberg, and serves as a key reason why people hang on to their iPhones.

 

Bailey’s exit is seen as a major loss within Apple, according to people with knowledge of the move. And there’s an awareness that it will presage a broader exodus of senior leaders in their 60s, they said. 

 

Apple is facing a demographic challenge: A generation of top executives, who became wealthy during their decades at the tech giant, are now reaching retirement age at the same time and no longer need to work.

 

Longtime general counsel Kate Adams is retiring this year, and environment chief Lisa Jackson left at the beginning of 2026. Former Chief Financial Officer Luca Maestri and longtime marketing head Phil Schiller have remained at the company in smaller roles but are likely reaching the end of their tenures.

 

Apple’s executive team includes several other veteran leaders who are approaching traditional retirement age. Cue in the services division, retail chief Deirdre O’Brien and marketing boss Greg Joswiak have all been at Apple for around four decades.

 

The most significant shift involves Tim Cook, who is stepping down as chief executive officer on Sept. 1. He’ll be replaced by John Ternus, the company’s hardware chief.

 

Ternus, 51, is expected to make own adjustments as CEO, including further personnel changes. He recently hired a retired hardware leader to join his management team.

 

Josh Rosenstock, a senior director of corporate communications who worked on financial and policy public relations, is leaving as well in an unrelated move.

 

Bailey’s payment division has been at the center of Apple’s push into financial services. The Pay app helped spawn newer offerings, like the Apple Card, and the company’s recently announced device upgrade subscription program.

 

The Wallet app, also overseen by Bailey, began mainly as a place to digitally store credit and debit cards but has expanded into other areas. It can now hold virtual keys for homes, cars and hotels, as well as identification cards.

 

Prior to helping launch Apple Pay, Bailey was the vice president in charge of the company’s online store. She joined Apple in the early 2000s after working at a range of internet firms.

 

Bailey is a familiar face to Apple fans, who have seen her present Pay and Wallet features at keynote events over the years. She has also been one of the most senior and influential female executives at Apple during her tenure.