SAN FRANCISCO--David Webster had a pretty busy year in 2009, trying to convince the world that Windows 7 was their idea and adding the word Bing to their collective vocabulary.

That said, Microsoft's chief marketing strategist doesn't foresee much time to rest. This year, all Webster has to do is persuade consumers that Office is cool, that Mom and Dad need their own Xbox, and that a Windows Phone can be a credible alternative to the iPhone. Luckily, Microsoft is willing to spend a few bucks to do all that.

"We're in a mode now where we are spending more money on advertising...than we have ever spent before," Webster said, during a lunch meeting last week. Microsoft doesn't break out figures, but the company is expected to spend roughly the same amount on advertising in 2010 as it did last year.

Microsoft

Microsoft plans to continue using the voice of customers to speak for the company. Webster said that Apple created a great opportunity for Microsoft when it turned Windows into the stodgy PC guy played by John Hodgman.

"Ultimately they made the choice to anthropomorphize the hardware platform to a human being," Webster said. "In so doing they are making a statement about our customers, not just our products. I think a lot of the work that we do really does do a nice job of taking that back and saying 'we're proud of who our customers are as they are proud of us.'"

That effort will likely spill over as Microsoft looks to do more consumer-oriented advertising for Office 2010.

Webster notes that while many people use Office for mundane tasks, the software also has surprising uses, ranging from a person who plans race course tracks in OneNote to people designing needlework in Excel. One friend of Webster does his Passover seder in PowerPoint with embedded sound clips from Charlton Heston in "The Ten Commandments."

"Office has a richer story to tell than we sometimes give them credit," he said. "People actually do a fascinating array of things."

One of the challenges for Webster and his team is that Microsoft's marketing dollars are split between categories where it is the 800-pound gorilla--like Windows and Office--and those where it is the upstart, such as Bing and Windows Phone. Although it is nice to be the leader, Webster says that products like Bing give the company more of a chance to experiment with new types of advertising.

For Windows, Microsoft plans to continue the current "Windows 7 is my idea" campaign, which Webster insists still has legs.

"We really think that we touched a nerve there," Webster said. It says we made your priorities our priorities. We focused on the things that you care about in focusing our R&D efforts."

That idea could span to other parts of the Windows business beyond the operating system, he said.

"It's actually an interesting way to think about talking about IE or Windows Live or even some of the PCs that our (hardware) partners are bringing to market."

Not all of Microsoft's bets last year paid off. For example, the company signed a deal for Windows 7 to sponsor a variety show by the creators of "Family Guy," only to promptly pull the sponsorship when the event proved too risque. Webster said that's probably an example where the company has a challenge both protecting the brand and keeping it relevant for a new generation.

"On the one hand, you can say 'Had you ever seen the Family Guy?'" Webster said. "Clearly we had. The issue was, if you want to reach a more student population, if you want to give Windows some cultural relevance with the younger population, 'Family Guy' is a property certainly (that could do that)."

He said that the idea sounded good on paper. "It's not crazy," he said. That said, as the event got closer and the company saw the scripts, it became clearer that it was not such a great fit. "I always say we reserve the right to wake up smarter every day and make better decisions. As we learned, as we got closer, we were able to call an audible (and pull out)."

And, while the idea of house parties for Windows 7 might have been a good idea, Webster concedes the companion instructional videos were "cheesy."

But, all-in-all, he said he applauds the fact that Microsoft is willing to push the envelope more.

"In the tech space, when you look at the companies competitively that we are going up against, I don't see a lot of risk taking, of being out there, in the moment," Webster said.

On the phone front, Webster notes that Microsoft has a challenge in going up against Apple, which is both the market leader and spends a fortune on its advertising for the iPhone. But he said, the big brands--Apple, BlackBerry, and Android--have kind of established their niche in the smartphone market.

"We're coming back to this party after the other guys have already played their hand," he said. "From a design standpoint, they are all more or less locked into the decisions they have made."

I pointed out that Microsoft appears to be going after a similar approach as Palm did with the Pre--positioning its device as the right phone for your whole life.

-- David Webster , chief marketing strategist, Microsoft "In the tech space, when you look at the companies competitively that we are going up against, I don't see a lot of risk taking, of being out there, in the moment."

"They probably did research that was similar to the research we did," he said. "I think they found some similar findings. There's a degree to which we deliver on that promise a little bit more holistically...I like our business odds."

As for Natal, Webster said that Microsoft does plan a big push, but he declined to give many hints. The Xbox add-on won't use Natal in its name, though he wouldn't say how it would be branded.

For his part, Webster is not your typical Microsoft guy. He was hired by Microsoft back in 2001 when he was working at branding consultant Siegel+Gale. He was pitching Microsoft for some business and was hired by Mich Mathews, the senior vice president in charge of the company's marketing. Webster did move from the East Coast to Redmond, Wash., but eventually convinced Mathews to let him move his family back to Connecticut where he could be close to both New York ad agencies, as well as the rest of his family, which he said are all congregated within about 30 miles of Manhattan.

Among Webster's ideas was the Mojave Experiment, where Microsoft filmed users' reactions with Windows Vista without telling them what operating system they were using. He's also been a big proponent of the need to do a better job of naming products. Even features within key products, he said, should be "word-of-mouthable." Webster points to the Shake and Snap features of Windows 7 as examples of features that have simple, easy-to-remember names.

That was also the goal, he said, with Bing. The company had several criteria in rebranding the search engine, he said. The company wanted a name that was one syllable and couldn't be misspelled and was as short as possible.

Webster said he initially came up with "Bang." The name had a few things going for it, he noted. "It's there, it's an exclamation point," he said. "It's the opposite of a question mark."

But somehow it didn't work as well when used as a verb.

"Oh, I banged it' is very different than 'I binged it'," he said.

In the end, he said, Bing proved to be a near-perfect choice, representing what he called "the sound of found."

"We really hit the jackpot with Bing," he said.