Hold or Fold 'Em? Odds for New Microsoft Ad Chief

Will CEO Ballmer Do Something Drastic and Hire 'a Palin'?

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NEW YORK (AdAge.com) -- Steve Ballmer wants Microsoft to have 30% share of the search market and earn 25% of its revenue from advertising in the next three to nine years. Both are tall orders -- and that's why the job of whoever helms the ad business, a spot vacated with Kevin Johnson's recent departure, will be so challenging.

Observers say it's going to take a very strong person to lead the ad team. "The DNA of the internet is so lacking at Microsoft," said one longtime Silicon Valley executive. "It could very well be mission: impossible."

Another said the company needs a drastic injection of energy, suggesting it hire "a Palin," shorthand for making an unexpected move. But while a surprise appointment would grab headlines, Microsoft also needs to prove to the Street it's serious about growing search share and making the internet business profitable. Who could accomplish that? Here are the four names mentioned most often -- and their well researched but wholly unscientific odds.

Brian McAndrews
Brian McAndrews, the Obvious Front-runner
Mr. McAndrews showed up at Microsoft little more than a year ago as CEO of aQuantive, its $5.9 billion acquisition, which closed just over a year ago. Since he joined Microsoft, Mr. McAndrews has concentrated on integrating the aQuantive divisions -- DrivePM and Atlas, at least -- and creating the vision of the Microsoft platform, the company's end-to-end buying and selling solution. Growing audience, one of Live Search's biggest challenges, is not Mr. McAndrews' responsibility, and he was consulted but not a central figure in the Yahoo deal.

The odds: 2-1. Shares of the aQuantive deal have vested, making Mr. McAndrews a very wealthy man. And while some wonder why he would stick around to work for a notoriously tough boss in Microsoft CEO Mr. Ballmer, Mr. McAndrews reportedly promised he would stay on for two years. Of course, most expect him to leave after that, which means the appointment could be just a temporary one.

Yusuf Mehdi
Yusuf Mehdi, the Lifelong Redmonite
A longtime Microsoft guy who has held leadership roles in many of the company's divisions, including the massive Windows unit, Mr. Mehdi helped orchestrate the aQuantive acquisition and was a point man on the Yahoo bid. Although that wasn't successful, people familiar with Microsoft said they don't believe that diminished his reputation in the eyes of Mr. Ballmer.

The odds: 3-1. First off, he wants to be at Microsoft. He has deal-making experience (Microsoft needs a few of those to get to where it would like to be) and he gets the Redmond culture. However, some suggest the company needs new blood, and the Street could frown on giving the job to a longtime insider, interpreting it as more of the same. One option floated: a power-sharing deal between Messrs. McAndrews and Mehdi.

Dan Rosensweig
Dan Rosensweig, the Outsider to Watch
The former chief operating officer of Yahoo and, before that, president of CNet Networks, Mr. Rosensweig has a pretty nice gig at the Silicon Valley outpost of Quadrangle Partners, the large private-equity firm. However, his firm has yet to do a big deal, and he could be getting restless. He's also well-respected as an operator, something Microsoft needs in this role.

The odds: 7-1. Microsoft has reportedly talked to Mr. Rosensweig, and the Street would look kindly on such a move, but he would be hard to lure to the job, according to people close to him. One scenario that could sweeten the deal: if Mr. Ballmer promises to take another run at Yahoo and allow Mr. Rosensweig to lead the combined companies. He left Yahoo rather unceremoniously and revenge is, of course, the sweetest success.

Jonathan Miller
Photo: Adam Hunger
Jonathan Miller, the Long Shot
Mr. Miller's stock has risen since he was ousted from AOL two years ago. The portal was struggling but largely seen as being on the right track when he was replaced by former NBC Universal Chief Operating Officer Randy Falco. Mr. Miller has since launched Velocity Interactive Group with Ross Levinsohn. Also handy for Microsoft: He knows what it's like to work for a demanding boss, having served under Barry Diller at what is now IAC.

The odds: 15-1. He's a long shot thanks to a noncompete clause that binds him until March 2009. But given that Microsoft is continually morphing, he could come onboard at a later date. Say after Redmond swallows up AOL?
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