Microsoft said corporate development VP and 12-year veteran Bruce Jaffe is "retiring" at the end of February. It did not give a reason for his departure.
Tech industry gossip site Valleywag.com, which first reported Jaffe's plans, speculated that he may be intent on launching a start-up.
During the past two years, Jaffe has helped oversee more than 40 acquisitions. Earlier this week, Microsoft disclosed a $1.2 billion bid for enterprise search specialist Fast Search & Transfer. In August, the company bought out digital ad agency aQuantive for $6 billion -- Microsoft's largest deal to date.
On Thursday, rumors that Microsoft was eyeing Logitech drove that company's shares up by as much as 12% in European trading. Microsoft has also been the subject of on and off speculation that it may attempt a buyout of Yahoo.
Jaffe joined Microsoft in 1995 as a member of the corporate strategy group. He was named general manager for corporate development in 2000.
Jaffe's departure highlights one of Microsoft's biggest challenges as a mature company -- attracting and retaining talent. In its early days, Microsoft could entice recruits with an entrepreneurial environment and stock options that would eventually turn secretaries into millionaires.
In 2008, however, it's hot Web 2.0 startups like Flickr and MySpace that are offering those kinds of perks. Jaffe, a Stanford MBA whose Microsoft bio describes him as a former entrepreneur, may simply be seeking a return to his roots.