Why The Changes Are Such A Big Deal

The flood of changes from Microsoft come as the company is experiencing strong growth, particularly around Azure and its other cloud offerings. For instance, Azure revenue rose 93 percent year over year in Microsoft's fiscal third quarter, ended March 31.

Ric Opal, senior director at Oak Brook, Ill.-based SWC Technology Partners, said the shift within Microsoft is "unquestionably the largest change that I've seen occur from a vendor while experiencing success. They're not doing this out of desperation."

"Assuming it's executed well, it should propel their long-term growth," he said.

Jackson echoed the sentiment. "They're super-successful right now, and yet they're still changing. I think that's an indication that they're future-focused, and have a vision for where this is all headed, and they're not complacent."