Apple Executive Behind the Launch of Apple Pay is Retiring After 25 Years

      Jennifer Bailey, who has led Apple Pay and Wallet since their inception in 2014, will be retiring in October after over 25 years with Apple. Her departure is part of a trend of senior exits ahead of Tim Cook transferring the CEO role to John Ternus on September 1. Eddy Cue, head of services, announced her retirement in a staff memo obtained by Bloomberg News, stating that a successor will be appointed before her departure.

      Cue remarked, “Under Jennifer’s leadership, Apple Pay has transformed the payment experience for hundreds of millions of users.” Bailey will continue to serve in an advisory capacity during the transition period. Apple did not provide any comments regarding her departure.

      The division she is leaving is among Apple’s most lucrative. Analyst estimates gathered by Bloomberg suggest Apple Pay generates over $7.5 billion annually and serves as an incentive for customers to remain with the iPhone. Bailey was also responsible for developing Wallet, which started as a tool for storing card information and has evolved to include keys for homes, cars, and hotels, as well as identification.

      Both Apple Card and the recently introduced device upgrade subscription originated from her division. Prior to her role with Apple Pay, Bailey managed Apple’s online store upon joining the company in the early 2000s from several internet firms.

      Sources close to the situation characterize her departure as a considerable loss and indicative of larger upcoming changes. Apple faces a demographic challenge as many executives who have accumulated wealth over years at the company are reaching retirement age and no longer feel the need to work. This year, general counsel Kate Adams is also set to retire, while environment chief Lisa Jackson departed at the beginning of 2026. Former finance chief Luca Maestri and marketing veteran Phil Schiller remain in reduced roles but are likely approaching their exits too. Cue, retail leader Deirdre O’Brien, and marketing head Greg Joswiak have each been with Apple for nearly four decades.

      The most significant shift will occur on September 1, when Tim Cook passes the CEO position to John Ternus and transitions to the role of executive chairman. Ternus, who has developed Apple’s hardware for over 20 years, is anticipated to implement further staffing changes and has already added a retired hardware chief to his team.

      The executive turnover isn't limited to the upper management level, as nearly all designers from the Ive era have departed Apple’s design studio—a gap Ternus plans to address. Additionally, Josh Rosenstock, a senior director in corporate communications, is also leaving, although Bloomberg reports this is an unrelated departure.