The Information reports how Jacob Andreou, the leader of Copilot experiences, told Microsoft staff in a memo last week that a coming Copilot overhaul should help the MS AI assistant “earn the right to exist” with users:
Microsoft Memo Details AI App Overhaul to ‘Earn the Right to Exist’ - The Information
“I’m sorry, who was this guy again?” If you don’t recognize the name, I don’t blame you. I didn’t remember him either and had to search for media reporting to figure out we’re talking about someone in a fairly senior position at Microsoft:
Jacob Andreou is the fast-rising Microsoft executive now leading the unified Copilot experience across consumer and commercial. He’s a former Snap product leader who joined Microsoft AI only in 2025. He has quickly become one of Satya Nadella’s key bets in the effort to turn Copilot from a scattered brand into a sharper, more competitive AI product.
The leadership shuffle at Redmond has been quite remarkable in the past year or so. Even before the broader voluntary retirement program (“VRP”) was announced for the general workforce, there was a steady stream of retirement announcements starting from the top. I had to ask my AI assistant to keep track of them and highlight the most impactful ones:
Rajesh Jha, the longtime head of Experiences + Devices, announced in March 2026 that he will retire on July 1 after more than three decades at the company. Phil Spencer, the longtime gaming chief, retired in February 2026 after 38 years, with Asha Sharma taking over Microsoft Gaming. And Yusuf Mehdi, a 35-year Microsoft veteran and one of the company’s most visible marketing leaders around Windows, Microsoft 365, and Copilot, said in May that he plans to leave after the next fiscal year.
This wave of senior leaders deciding to quit Microsoft isn’t exactly surprising, given what the tech media reported already last fall. According to executives that talked with Business Insider anonymously, Satya was pushing on intensity and urgency unlike ever before. "You've gotta be asking yourself how much longer you want to do this” was a quote that told a lot about the sentiment inside the org.
Now when FY26 came to a close, we’ve seen a wave of retirement posts on LinkedIn as many familiar Microsofties we’ve known to represent the company since forever have handed in their badges. It has certainly not been a sudden decision for many of them, given how it has been widely reported that employee morale had already hit an all-time low inside Microsoft last summer. I recently revisited a Reddit thread about the layoffs and toxic management culture at Microsoft to reflect on what some employees (anonymously) wrote to these public forums.
r/microsoft comments on toxic management 1y ago vs. MS stock value diving in 2026.
At that point in time, the contrast between employee experience and company financial performance was indeed stark:
“I know so many people at Microsoft either on leave for burnout or who have left over the past 12 months. Good people. Top performers who are just tired of giving their all for diminishing returns. The company has the highest stock price in its history. We are beating earnings estimates quarter after quarter. We have never been stronger. So why does it feel like it is literally the worst time to be at Microsoft?”
A year later, the people side of the company may or may not be better or worse. One thing’s for sure, though: the highest stock price in history is a distant memory. In June 2026, Microsoft had its worst month since the dot-com era of 2000 — although one must mention that none of the other stocks from the Magnificent 7 had a great month either. In a YoY comparison with the other two hyperscalers, Microsoft is down roughly 20%, Amazon is up 10% and Google is up 100%. That’s gotta cause some tension in the Redmond C-suite.
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