Apple is entering its most significant leadership transition in more than a decade as multiple senior executives prepare to depart and CEO Tim Cook begins to shape the company's next generation of leaders, according to Bloomberg's Mark Gurman. In the latest edition of his "Power On" newsletter, Gurman explained that Jeff Williams, who was viewed as Cook's potential successor for several years, has already handed off his operations responsibilities and will leave the company later this year. His exit marks the first major change in Apple's senior leadership since 2019, when both Chief Design Officer Jony Ive and retail chief Angela Ahrendts departed. Gurman reports that this change is the beginning of a broader reshuffling among Apple's top executives, many of whom have been in their roles for more than a decade. Former Apple marketing chief Phil Schiller continues to oversee the App Store and product launch events after stepping down from day-to-day operations in 2020. Former Chief Financial Officer Luca Maestri, who resigned last year, still retains oversight of Apple's real estate and information systems. However, Gurman writes that the company's era of stability "cannot last forever," noting that several executives are now weighing retirement or changes to their roles. One of the most closely watched figures is John Giannandrea, Apple's senior vice president of machine learning and AI strategy. Recruited from Google in 2018, Giannandrea has led Apple's efforts in artificial intelligence, including the rollout of Apple Intelligence. Gurman states that his position "has been uncertain for years" following setbacks with Siri's redevelopment and internal struggles over Apple's AI direction. Some of Giannandrea's responsibilities have been reassigned to Mike Rockwell, who previously led the Vision Pro and is now tasked with improving ‌Siri‌. Gurman also reports that Apple is considering external candidates to strengthen its AI leadership. Among them is a senior AI exe