Apple Pay and Wallet Services chief Jennifer Bailey is leaving the iPhone maker

Apple’s longtime head of Pay and Wallet services, Jennifer Bailey, is retiring after more than two decades at the company, marking another senior leadership transition at the iPhone maker, Bloomberg reported on Tuesday.

Apple services chief Eddy Cue announced Bailey’s departure in a staff memo. Bailey, who has served as vice president of Apple Pay since the service was launched in 2014, is set to leave the company at the end of October. She will remain available in an advisory role to support the transition, Cue said.

“Under Jennifer’s leadership, Apple Pay has changed the way hundreds of millions of our users pay,” Cue said in the memo. Apple will announce a succession plan before Bailey’s departure.


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A spokesperson for Cupertino, California-based Apple declined to comment on Bloomberg's request.

Bailey’s exit is considered a significant loss for the company, according to the publication's sources as her departure comes at a time when Apple faces the prospect of a broader turnover among senior executives who are approaching retirement age after decades at the company.

Apple’s senior leadership has already seen several changes. Longtime general counsel Kate Adams is retiring this year, while environment chief Lisa Jackson left the company at the beginning of 2026. Former chief financial officer Luca Maestri and longtime marketing chief Phil Schiller continue at Apple in smaller roles, but their tenures are also expected to be nearing an end.

Several other veteran executives are approaching traditional retirement age. Cue, retail chief Deirdre O’Brien and marketing chief Greg Joswiak have each spent around four decades at Apple.

The biggest leadership change is at the top, with Tim Cook set to step down as chief executive officer on September 1. He will be succeeded by John Ternus, Apple’s hardware chief, who is 51.

Ternus is expected to make changes to the company’s leadership team after taking over as CEO. He has already brought a retired hardware executive into his management team.

Separately, Josh Rosenstock, a senior director of corporate communications who worked on financial and policy public relations, is also leaving Apple.

Bailey’s Pay division has played a central role in Apple’s expansion into financial services. Apple Pay, which enables users to make purchases in stores and online, has become a major business for the company. Analyst estimates compiled by Bloomberg put its annual revenue at more than $7.5 billion. The service has also become an important part of Apple’s broader ecosystem.

The Pay business helped pave the way for products including Apple Card and the company’s recently announced device upgrade subscription programme.

The Wallet app, which Bailey also oversaw, has expanded significantly from its original role as a digital repository for credit and debit cards. It can now store virtual keys for homes, cars and hotels, as well as identification cards.

Before helping launch Apple Pay, Bailey was Apple’s vice president in charge of its online store. She joined the company in the early 2000s after working at several internet companies.

Bailey has also been a prominent presence at Apple product events, where she regularly showcased new Pay and Wallet features. During her tenure, she became one of the company’s most senior and influential female executives.

The memo from Apple’s Cue, as accessed by Bloomberg:

After more than 25 years at Apple, Jennifer Bailey has decided to retire in October. During her tenure, Jennifer has made extraordinary contributions from leading the Apple Store Online through a period of significant growth and global expansion to overseeing the launch of Apple Pay.

Under Jennifer’s leadership, Apple Pay has changed the way hundreds of millions of our users pay, with a simpler, more secure, and private experience. She also led the development and growth of Apple Wallet, oversaw the development and launch of Apple Card, and led our work in Services fraud prevention and partner operations, Gift Cards, and Trust and Safety. And those are just a few of her achievements.

On a personal note, Jennifer has been an incredible friend and leader, and I will miss working with her.

Please join me in thanking Jennifer for her incredible contributions to Apple. 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.

As we continue to work toward our vision of replacing the physical wallet, I’m more confident than ever in the work that we are all doing and look forward to an exciting future ahead.

Thank you,

Eddy