Apple is heading into a new chapter, and the transition is looking a lot messier than the company would probably like.
With CEO Tim Cook set to hand the reins to John Ternus in September, a wave of veteran executives is quietly weighing whether to stick around for the next act.
At the center of it all is Mike Rockwell, the executive who built the Vision Pro from the ground up. Rockwell has been considering leaving Apple or stepping back into an advisory role as early as next year, according to a new report.
He Had Bigger Plans in Mind
Rockwell’s ambitions extended far beyond hardware. Sources familiar with the matter say he was once considered for a role akin to Chief Technology Officer, which would have granted him oversight of Apple’s entire product and AI strategy.
The idea was that head-worn wearables would become the foundation of Apple’s future after the iPhone, with Rockwell steering that ship.
That vision has not played out the way anyone hoped. The Vision Pro launched at $3,499, and while the hardware impressed many, the price and the device’s sheer weight kept mainstream buyers away.
Apple is still working on smart glasses and other wearable tech, but Rockwell’s path inside the company looks far less clear than it did a couple of years ago.
Now He’s Running Siri, and the Clock Is Ticking
In March 2025, Rockwell took over the Siri project after Tim Cook lost confidence in the AI work being done under John Giannandrea.
The voice assistant was pulled entirely away from Giannandrea’s team, and Rockwell stepped in to lead what is shaping up to be a complete overhaul of the product.
Rockwell is unlikely to walk out the door before that overhaul is finished. The revamped Siri is expected to arrive with iOS 27, so his timeline at Apple probably extends at least through that release.
One complicating factor is that he reportedly has reservations about reporting to Craig Federighi, Apple’s software chief, and wants a broader scope than his current role offers.
He’s Not the Only One Thinking About the Exit
Retail and HR chief Deirdre O’Brien has told colleagues she is considering retirement. Government affairs head Kate Adams is already set to retire later this year.
And then there’s the group of long-timers who are each approaching 40 years at Apple: marketing chief Greg Joswiak, App Store head Phil Schiller, and services boss Eddy Cue. Any one of them stepping away would be a significant moment in itself.
For Ternus, walking into the CEO role means inheriting a company that could look very different at the top by the time he gets settled.
Whether that kind of turnover becomes a real problem depends a lot on how smoothly the Siri relaunch goes and whether Apple’s wearables story starts to click with consumers in a way the Vision Pro never quite managed.
