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Creating a fresh pitch about an established product is a hard enough job. But what if a billion consumers already own the previous version of it? For David Webster, general manager and chief strategy officer for Microsoft's central marketing group, that was the key sticking point as he and his team figured out how to market Windows 7.

Well in advance of the operating system's October 2009 launch, Webster's team knew the campaign would need both a high-impact message -- and one that would build on the existing perceptions so skillfully set up by the now-legendary "I'm a PC" campaign. That series of TV spots via Crispin Porter + Bogusky effectively deflected Apple's poison darts with the message that PC users weren't just average joes, but in fact millions of highly creative people all over the world.

"Windows 7 was a great moment for us to put a punctuation mark on [the 'I'm a PC' campaign]," says Webster. Make that an exclamation point. Windows 7 now ranks as the fastest-selling operating system in Microsoft history, with more than 175 million licenses sold to date. Seven licenses are sold every second. Customer satisfaction is the highest that Windows has ever seen, at 94 percent, according to the company.

While those numbers don't directly reflect the campaign's results, others are more indicative of what Webster hath wrought. "The key perceptions on all the key attributes are meaningfully higher among the folks who have seen our ads versus the ones that haven't seen our ads," he says.

Webster recalls that the creative juices for the campaign started flowing in earnest when he wrote a speech for a Microsoft engineer about a year and a half before Windows 7 was released. At the time, the beta for Windows 7 was in full swing. And it was a doozy; some 8 million consumers were providing Microsoft's engineers with feedback on what got them excited and what didn't.

One of the key messages in the speech was that "Windows 7 reflects us listening to our customers," Webster recalls. "The most unique thing about this product isn't feature A, B or C. It's that our customers really played a very active role in helping us design the whole thing. ... Our customers are, in fact, our colleagues." The speech received a great reaction. So did the idea when Webster did some message testing a month later. For this reason, it was front and center in the creative briefing that Webster gave to Crispin.

There was a danger, however, that needed to be sidestepped in the process. "If you stray into some grandiose proclamation of how it's going to change [a consumer's] life -- and they already use the product and that doesn't match how they feel about it today -- you're not going to have very effective marketing," Webster says.

Instead, the agency aimed for a more disarming approach that would also make it more difficult for the competition to spoil. In the process, the comfortably possessive aura of "I'm a PC" took a whole new shape for Windows 7 in a campaign called "My Idea."

The ads featured young people revealing how different aspects of the software met their unique needs. There's the American college student in Germany, for example, showing off a video of himself doing push-ups (with his tongue, no less) -- a video he accessed on his home computer back in Austin, Texas. There's the dork locked out of his dorm room, dreaming of becoming a babe magnet with the system's DVR-like capabilities. Out-of-home ads featured striking portraits of earnest-looking young people along with quick-hitting captions. One shows a brainy-looking dude staring through a pair of thick black, square-framed glasses. "I asked for less clicks. Now it takes less clicks," the ad reads. "I feel drunk with power." The message, delivered with sharp, dry humor, was clear: You helped us design this software, and now it does the stuff you need. One ad (which also ran online) states exactly that: "I'm a PC," says a young Asian guy with a mohawk, "and Windows 7 was my idea."

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.   


David Webster photographed by Greg Kessler