Did Ballmer Blow It With Carolyn Everson? (Updated)

Did Steve Ballmer blow it with Carolyn Everson?  

That’s the question some are asking inside the software giant, which is finally coming to terms with last week’s news that Everson, Microsoft’s global ad sales leader, has jumped to Facebook after roughly nine months on the job.

Obviously, the opportunity to run global ad sales at Facebook—a company that has an opportunity to redefine an ad medium—is one that few in digital media would be able to turn down. Yet according to sources, Everson had been sending every signal that she was committed to Microsoft but may have been deterred after spending a few days with Microsoft CEO Ballmer in Las Vegas during the Consumer Electronics Show last month.

Under Ballmer’s reign at Microsoft, the company has moved aggressively into online advertising—specifically chasing after Google’s search business with the launch of Bing and the subsequent partnership with Yahoo. Yet doubts have long lingered that Microsoft is not fully invested as a media company. Its Online Services Division—where MSN and Bing are housed—continues to hemorrhage dollars. And the thinking among many insiders is that Ballmer couldn’t care less about the MSN portal or selling display advertising overall.

Apparently, that was the verdict Everson came away with after spending time with Ballmer in Vegas—an impression that helped her make the decision to leave the company so abruptly, according to sources inside Microsoft.

Not everyone at Microsoft agrees. “That’s overstated,” said one source. While Everson was said to be frustrated with the amount of traffic and resources Bing was receiving over MSN’s partners, that issue had been addressed prior to her decision to leave. “The U.S. business is actually in really good shape at MSN,” said an insider.

On Thursday (Feb. 24) Everson herself looked to paint a more cohesive picture of her Microsoft tenure and her relationship with Ballmer in a posting on her Facebook page. “I am leaving Microsoft for a new and amazing career opportunity,” she wrote. “I am deeply grateful to Steve Ballmer and the team at Microsoft for their professionalism, talent and the wonderful experience they gave me. They’re a great team and I look forward to seeing their continued success.”

Regardless, Microsoft executives were caught flat-footed with Everson’s announcement, considering that it took six months to recruit the former Viacom executive. They are likely to re-examine the company’s sales structure before hiring a replacement.