Microsoft's Frank Holland Talks Custom Versus Automated Campaigns

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In April, Frank Holland will mark a year at the helm of Microsoft's ad sales efforts. In that time he has met with many of the company's global agency and brand customers, and has sought to channel the energy of his 1,800-strong sales force into the kind of custom, high-touch campaigns brand advertisers increasingly want. It hasn't been easy.

"The problem we have right now is we don't have enough sales people to address the demand for high-end, multi-screen branded deals," said Holland, corporate VP of advertising and online business.

The notion that employing close to 2,000 ad sellers amounts to a staffing crisis may seem ludicrous until you consider the company's sprawling media network. Among Microsoft's ad supported properties are Xbox, MSN, Skype, Windows Live, Windows Mobile, Hotmail, Microsoft Media Network (a comScore top 10 ad network), Bing, and Yahoo Search. Many of these have specialized ad formats and dedicated sales teams.

Also consider that Microsoft's sales organization is divided into 13 regions, of which the U.S. is just one. Overseas its job is further complicated by franchise deals with brands like Singapore's XIN, for content and ad services.

In the U.S. and internationally, Holland wants his ad sellers to focus on lucrative customized campaigns. "I'd like to cover the creative agencies a lot deeper than we do today, and have them think about the Microsoft opportunity as a platform they can build on top of," he said.

Holland insists this will happen naturally as Microsoft puts in place better systems for automating data-driven display ad campaigns. He said programmatic ad buys represent the fastest growing piece of Microsoft's ad business, revenue-wise.

Microsoft's programmatic offering is a work in progress, but it includes ad exchange technology supplied by AppNexus and the company's big ad network deal with rivals Yahoo and AOL. That deal became official earlier this month.

"We end up solving a lot of problems with arms and legs that we could with a really advanced platform," he said. "As we get more advanced in the way we automate programmatic buying, we'll be able to service a lot more depth on the hand-sold side."

A Microsoft Insider

Holland has little in common with his predecessors. The two most recent people to hold his job at Microsoft were Robin Domeniconi and Carolyn Everson, hailing from MTV and Time Inc., respectively. Both were seasoned media sales execs and neither lasted very long. After leaving Microsoft, Domeniconi moved on to Elle, and Everson famously went to Facebook.

Holland, on the contrary, was promoted from within after some 14 years in enterprise sales.

So what's his pitch to advertisers? In a word: breadth.

"Facebook has done a very nice job of taking the term social and making it equal to Facebook," he said. "I'm not trying to define a particular property or platform as the thing Microsoft is going to stand for."

Holland holds up Skype as an example of Microsoft's strength in social. "I'm not trying to hit a zillion friends with Skype," he said. "I'm trying to allow brands to have a co-conversation with the eight closest confidants you've got in the world."

Holland says Microsoft has a very high standard for what advertising should look like in the future.

"It's pretty different from what it looks like now," he said. "In 15 years, here's the legacy I would like to have left: It would be about introducing advertising that's relevant, that's beautiful, that's engaging, that's useful to a consumer. Right now we're a little bit hobbled by the fact we don't connect the pieces of the ecosystem, including the media and creative agencies, well enough to make that happen."