No, not talking about the one and only Phil Schiller (who I swear to God might be immortal). But I am talking pretty big figureheads within the company like Lisa P. Jackson (last seen on the roof of Apple Park’s main looping campus), Alan Dye (VP of Human Interface Design; best known for Dynamic Island and Liquid Glass), and earlier this year, its own COO Jeff Williams¹. In terms of Jackson, she’s retiring, having previously served under President Obama’s administration many years ago as President of the US EPA. She left the US EPA for Apple in 2013, a little bit after Obama’s “transition” into his second term in office.

Under normal circumstances, leadership shakeups on this scale would cause alarm. And to some extent, they absolutely have–especially with the Apple Intelligence fumbles and alleged internal leadership drama.

I’ve seen a lot on Twitter today alone about this leadership shakeup, and what it means for Apple going into 2026. But as I wrote to friend of the blog Lucia Scarlet in a Tweet on Alan Dye’s replacement, Steve Lemay: “[I’m] gonna keep my hope tempered for now, but i [sic] have this feeling in my stomach that we might be in good hands!”

Alan Dye’s probably the more interesting departure here. He’s heading for Meta to fill a new role within its Reality Labs division, which will be interesting to see what comes out of that. The new leader is Lemay, who has been working on Apple’s designs in some form since 1999.²

John Gruber writes of Alan Dye (in a great piece):

The most galling moment in Dye’s entire tenure was the opening of this year’s iPhone event keynote in September, which began with a title card showing the oft-cited Jobs quote “Design is not just what it looks like and feels like. Design is how it works.” The whole problem with the Dye era of HI design at Apple is that it has so largely […] been driven purely by how things look. There are a lot of things in Apple’s software — like app icons — that don’t even look good any more. But it’s the “how it works” part that has gone so horribly off the rails. Alan Dye seems like exactly the sort of person Jobs was describing in the first part of that quote […]

I quote this section (mostly) in full because, quite frankly, no one says it better than Gruber. In the case of Alan Dye, he simply didn’t meet the moment. I agree that it was time for a new approach to the designs of Apple’s OS platforms, but in Dye’s tenure it has led to a lot of issues. Especially on macOS. It was no surprise to see reporting that OS 27 releases from Apple in 2026, at least on iOS, will focus primarily on bug fixes — much like “OS X Snow Leopard” did back in the day.

When Jony Ive left, part of Apple’s design philosophy also died. He was one of the last who really worked with Jobs on a personal level, and knew what he wanted the company to be. I’m going to be up front with you, Jobs made the company what it was. He was a huge reason for it ‘being.’ He was a visionary, much like Ive, and I’m willing to bet real hard-earned money that that is why Jobs and Ive got on so well when it came down to it.

And Apple’s been about playful, unique, and often controversial designs³ that drove the rest of the industry forward since the introduction of OS X.⁴ Apple has historically been perhaps not the first to the game, but almost always the trendsetter when it comes to moves. See the headphone jack’s removal and transition to Bluetooth earbuds/headphones, the move to USB-C on laptops and desktops⁵, and even simpler things like facial and fingerprint recognition sensors.

Yes, you can successfully argue Android did that stuff first — because it did — but Apple did it well, and a lot of Android vendors started trying to copy their homework. A lot of them haven’t even got the security part of “Face ID” down yet⁶, so there’s that.

The truth is, I don’t know if there’s much to gather from these leadership changes. Jackson oversaw Environmental initiatives which is transitioning under someone else (and is also 63, right around retirement age). Jeff Williams retired early at 62. All of these people have a lot of money and didn’t leave for a rival company like Dye did. In my opinion, Dye’s the more interesting leave to keep an eye on.

I’m hoping Lemay’s the change Apple needs in the design department. My hope is that he can take Liquid Glass and improve upon it to a state where it’s actually usable, more specifically on macOS. Only time will tell, but I have my hopes up just a little bit...

If you have any info on this story or anything you might want to share, consider sending it to me on Signal at sladewatkins.06. I’m all ears!

1. Long speculated to be the successor to Tim Cook, Williams instead announced his retirement in July 2025. To my knowledge, he was best known as the one who oversaw Apple Watch. ↩︎
2. Jobs reportedly used to call him “Margaret.” I’ve also seen at least two ex-employees speak highly of him scrolling around Twitter tonight while writing this story. ↩︎
3. A tiny history lesson here: Skeumorphism went away with OS X Yosemite (having been used heavily from OS X’s original release “Cheetah” up to OS X Mavericks). It then came back (somewhat) in macOS 11.0 Big Sur. With the release of macOS 26.0 Tahoe, however, it has gone to 3D glass much like the rest of Apple’s platforms. It doesn’t look great. ↩︎
4. For a modern example: skuemorphism went away in Apple’s software, Google eventually released Android 4.4.4 KitKat — which chipped away at the Holo interface just a tiny bit — and eventually landed on Android 5.0 Lollipop with its current “Material” language. For a more retro example: See Windows Vista and 7’s Aero theme that was so freaking good that I wish it was back in Windows. (Microsoft, take notes!) ↩︎
5. I’m not counting phones, because let’s be honest, that was the EU’s doing — not Apple’s. And Google has de facto mandated it for all Android manufacturers since Android 10 (and said devices with USB-C ports must have USB-C PD compatibility). ↩︎
6. On my Pixel 10 Pro XL and Pixel 10 Pro Fold from Google, which I’ve been using since October due to the whole mess with Liquid Glass (waiting it out a bit), Face Unlock is just taking a photo of my face so it doesn’t work in the dark or dimly lit rooms… which I’m in all the time. So it’s useless compared to my iPad Pro (M4), iPhone 17 Pro and Pro Max’s Face ID sensors. It’s not a fancy 3D scanner array like on the iPad Pro or iPhone with the TrueDepth camera system, and I have successfully fooled it with a printed photo of myself before on my Pixel 8 and both of my 10 Pros. So yeah, I really wish it was an actual 3D scanner array! ↩︎