David Webster, Microsoft

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Crispin’s well-known creative muscle notwithstanding, colleagues laud Webster for his personality and management style—in particular the way he stirs creativity in others. “He has such a genuine quality that you kind of feel comfort. That’s something we don’t put enough stock in—the people in the room who are calming,” says Rob Reilly, partner and co-CCO at Crispin. “The pressure at Microsoft is pretty massive. But David’s that voice in the room that continues to bring ideas and smart thinking in a way that’s easy for everyone.”

“He’s got one of the most brilliant, strategic minds I’ve ever come across, and he’s an incredible orator, too,” adds Mich Mathews, svp of Microsoft’s central marketing group. “David has this ability to persuade you of a viewpoint, [then] some kind of magic kicks in. And his command of the English language is profound.”

And, as though the kind of motivating and communicating innate to Webster’s job were not difficult enough in an organization as large as Microsoft, consider that he works from the other side of the continent—out of his home in Connecticut. Webster was able to cement personal relationships at the company by first working at the mother ship for seven years before relocating. It’s a testament to the esteem his colleagues have for him that a 3,000-mile distance is not an impediment to the work. In fact, Webster says it’s actually an advantage. A country’s worth of distance, he says, allows him to take a more dispassionate view of Microsoft’s products and those of its competitors. (It also allows him to spend more time with JWT in New York, which handles the advertising for Microsoft’s search engine, Bing.)

Webster’s biggest challenge today, he notes, is the marketing plan for the new Windows Phone that’s coming out this fall. “We’ve been in the phone space with Windows Mobile for six or seven years,” Webster says. “But we took the hard decision to completely reset that platform and come out with a completely new product.”

He notes the bombastic, fiercely competitive nature of the mobile market, and how Windows will need to make a unique case. But “I’m really excited about what we’ve come up with creatively there. You’ll have to wait and see in the coming months how it all plays together,” he says. It seems a pretty good bet that it’ll play just fine.

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The Gentleman Starts His Engine
 
David Webster divides the products he markets at Microsoft into two categories, incumbents and challengers. And while Windows falls in the incumbent category, one of the biggest challengers he’s worked on of late is Bing—the search engine aiming a punch at the 800-lb. gorilla of the search market, Google.

To say that Webster had hands-on involvement in Bing would be an understatement; he was, in fact, a key voice in coming up with the product’s name. “It was really intense,” Webster says of the early days of the campaign, a $80-$100 million effort helmed by JWT. “We weren’t going to get another chance at this,” he says. “It was very much a measure-twice-and-cut-once kind of moment.”

Aware of the general perception that many people already consider Google to be reasonably good, Webster and JWT elected to take aim at search engines in general—specifically, the fact that most searches produce what JWT spots later termed “search overload,” or endless screeds of information that have little or nothing to do what the user’s actually looking for. Darkly humorous ads pointed out this kind of information gridlock (one of them showing everyday people attempting to have ordinary conversations but spitting out psychotic-like streams of facts instead), and introduced Bing as “the first-ever decision engine.”