Mike Rockwell, the Apple executive who led development of the Vision Pro and is now in charge of rebuilding Siri, has considered leaving the company or moving into an advisory role as soon as next year, according to a new Bloomberg report by Mark Gurman.

Rockwell is said to have reservations about reporting to his new boss, software chief Craig Federighi, and wants a bigger remit than the one he currently has, according to people with knowledge of the matter who spoke to Gurman. Rockwell was apparently once lined up for a role defining Apple's product and AI roadmap – something close to a chief technology officer position – on the assumption that head-worn wearables would form the foundation of Apple's post-iPhone era.

However, that trajectory has gone south because the Vision Pro has struggled to find a mainstream audience, with many put off by its $3,499 price tag and physical heft. Apple is still developing smart glasses and other wearables, but the picture for Rockwell is decidedly murkier than it once was.

Rockwell took on the Siri project in March 2025 as part of a wider reshuffle, after Tim Cook lost confidence in the AI work being done under former AI chief John Giannandrea and reassigned the voice assistant away from his team.

Gurman reports that Rockwell is unlikely to walk away before finishing the Siri overhaul, which is now expected to arrive as part of iOS 27. He is one of several senior Apple figures who are said to be weighing their next move as John Ternus prepares to take over from CEO Tim Cook in September.

Among them is retail and HR chief Deirdre O'Brien, who has told colleagues she is considering retirement, while government affairs head Kate Adams is set to retire later this year. Marketing boss Greg Joswiak, App Store head Phil Schiller, and services chief Eddy Cue are all approaching four decades at the company, raising the prospect of further departures during Ternus's watch.