Of all the many executives on the Microsoft “Senior Leadership Team,” called SLT for short, it’s pretty clear in talking to top execs that there is no one that engenders more talk than Mark Penn.

He currently reports directly to the CEO as EVP of Advertising and Strategy — having been hired full-time by his longtime friend Steve Ballmer in mid-2012, first as a strategist.

Inside Microsoft, then, many are waiting to see what new CEO Satya Nadella does with Penn, who is currently matched in a classic and problematic two-in-a-box face-off with EVP of marketing Tami Reller.

Reller took the job, of course, knowing the score, but apparently was focused on balancing Penn’s more aggressive tendencies.

In any case, according to many, the set-up has been uncomfortable and, increasingly, untenable, with sources noting that some big change in this key area for Microsoft is expected very soon.

The question: Will Reller, one of the top women execs at Microsoft, depart or could Penn — less likely — be moved aside? If she leaves, will Penn get to run the entire marketing org or will another internal or external candidate be brought in to continue to balance him?

Possible internal execs who could take the job include longtime marketing execs Yusuf Mehdi and Chris Capossela.

More importantly, whether Penn lands an even stronger role or is moved to a lesser one will be a very interesting indicator of the kind of leader Nadella will be.

Many, Nadella among them, consider Penn smart — “whip-smart,” “deeply smart,” “scary-smart” are among the ways other execs describe him. But he is also someone who has a reputation for divisiveness that has become problematic to some.

“In a very political place, he stands out as the most political creature here,” said one exec in a common refrain. “He is very much a lightning rod and obviously a symbol of the Ballmer regime.”

Penn, of course, fits the bill of that kind of aggressive character. The famous political operative, who was a top adviser for campaigns for both Hillary and Bill Clinton, was known for his highly negative style of advertising. If you remember the 3 am phone call spot against Barack Obama in 2008, whom he also insinuated took drugs, you will quickly get the kind of messaging he specializes in.

As in: Not. Very. Nice.

When he arrived at the software giant, that tone did not change one little bit. In fact, his abilities to depict the worst was precisely the talent that the already pugnacious Ballmer hired him to use — punch back hard against all rivals and, well, punch even if there was no fight to begin with.

The name given his employees — largely based in Washington, D.C. — is as a “multidisciplinary SWAT team,” according to his profile on Microsoft’s exec page.

Swat indeed. Penn was the driver, for example, behind the famous — some think infamous –“Scroogled” campaign that shows Google to be a modern-day version of the Borg, nefariously sucking up information of the people of Planet Earth and monetizing it greedily. Penn has also attacked Apple, in ads that pretty much fell flat.

Much of the fare is broad and tasteless, which is not always a bad thing. Perhaps more damning is that some of it — especially Scroogled — appears to have been pretty ineffective in general, although Penn has used data at internal meetings to claim it has not.

My take is to ignore that data, because perhaps a company that has had a longtime bullying reputation looks idiotic and tin-eared calling others a bully.

Still, sources said Nadella is not averse to continuing the aggressiveness, although more recent big ads from Penn have been warmer and fuzzier, such as the Superbowl ad called “Empowering,” which is clearly a two-hankie weeper.

One thing that has been welcomed at Microsoft is Penn’s relentless focus on using data to determine what works, which is much lauded within, although some think he also manipulates it to his advantage.

Along with whether data should be the key determinant of an ad, there is, in fact, something unusual in that Penn is responsible for measuring the effectiveness of an ad he created. (Hey everyone: I give myself an A+++!)

“There was not a real rigor to testing how advertising went over with consumers before and Mark is very good at that,” said another exec. “That said, he also is the one to tell us how good he is performing.”

In his Microsoft bio, Penn’s group’s goals are described as “creating world-class advertising and messaging to consumers and business customers delivered through the most cost-effective and scientific means available. Based on state-of-the-art research and data tools, the campaigns aim to inspire our customers, incite our fans and turn around doubters.”

Doubters exist within Microsoft about the kind of marketing strategy that Penn has advocated. Then again, in every election, there are always two sides.

A Microsoft spokesperson declined to comment, but here is a Jekyll and Hyde version of Penn’s work, plus the famous Obama ad:


Yeah, some bozo tells you how great he is at his job and you're the one who is responsible for believing him. I heard this in the first day of journalism 101 - "Your mother says she loves you? Check it out." If people in positions like his were held to such a standard, there would be much less of a mess at places like Microsoft, Google, Samsung, HP, Dell… the list goes on and on.

It's like they all taken in by "The Toyota Way" lean scam that's the darling of CEOs everywhere. Microsoft management is tone deaf when it comes to criticism of their methods. The echo chamber is deep there. It's going to take more than sacking Ballmer to fix it.


Now it's the perfect time for MS to relaunch itself, he should bring in new people to do the ads and marketing.

Nadella's decision to give Elop xbox and devices already made me doubt his judgement.... 


They should all go.

Microsoft's marketing in domain of consumer products is nothing short of a disaster. 

They do not succeed in communicating what their products are good for - I had more than one revelation moments when someone told me "well, x-box can do that" or "why don't you use the windows media center for it". And the features were indeed there, and they are cool. Too bad that I never hear about these features from Microsoft's marketing.

I have impression that the issues is even more emphasized outside of US. 

Their attempts at promotion of WP8 in Germany are embarrassing to watch (for instance, the official WP8 twitter channel looks like it was hacked by a 15 year old).

Finally, even the Microsoft employees I talked to hate their own marketing. When one speaks to them, officially they are not allowed to comment on it, but unofficially they hate it and they hate the fact that nothing can be done about it.


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