Desperately Seeking Buzz ads are pushing the envelope. Will they work?

The definition of hell, a CEO once told me, is four, two-hour meetings a day. And the six folks gathered around a conference table in the Los Angeles high rise where I'm sitting are living it: One is snoring audibly; another is harvesting unspeakables from his ears, eyes, and nose; another falls dead asleep, his forehead bouncing on the table. The door opens, mouths gape. In struts transvestite diva RuPaul--seven feet tall in a teased big-hair blonde wig and a pythonesque green and blue dress. "This meeting is a real draaaaaag," he snarls with a sassy flick of his neck.

"That's it!" cheers David Thompson, vice-president of marketing for San Jose-based WebEx Inc. We're actually watching this unfold on a tiny monitor right outside the meeting room. We are witnessing director Mark Bennett film a 30-second commercial spot that will run during the Jan. 30 Super Bowl, advertising's annual Valhalla. "That line is going to go down in history. It has water cooler resonance. And we're all going to be doing that neck thing," howls Thompson. Laughs Kelli Christman of the Free Range Chicken Ranch agency, which is producing the spot: "There will be personal trainers who teach that."

Welcome to the ebullient front lines of the war for mindshare. WebEx is spending many millions on this campaign to make its service, which lets people meet online and share documents in real time, a household word--about $1.2 million just to secure the Super Bowl time slot for major markets. And RuPaul's big hair, big teeth, and shapely gams are appearing on giant billboards; his sexy patter in radio spots. But if Thompson feels an iota of uncertainty about putting his company's future in the hands of a 1,000-watt drag queen, well, he sure doesn't show it. He scoots around the set grinning like the proud father of the bride, his booming laugh reverberating. Muses director Bennett, who has directed other spots for Web startups: " clients are more open-minded. They're not mired in the tradition of bad advertising. The concepts are younger, more entertaining."

No argument there. Creative campaigns from the likes of E*Trade and the sing-song silliness of Yahoo! have injected a blast of fun and excitement in the ad scene. But most of these reach out to consumers. WebEx is a so-called business-to-business upstart. Brochures for the four year-old company explain its technology offers "scalable architecture for multi-media collaborations." That's geek-speak for software that lets people use their browsers to collaborate online. But it also makes hiring RuPaul as your corporate spokes-uh, well, person, about as natural as tapping Madonna to hawk Chase Manhattan's corporate bond group; or maybe "Stone Cold Steve Austin here for SmithKline Beecham."

IPO AHEAD. But this is the Internet, 2000. Startups like WebEx believe they have no choice but to set themselves apart from the yammering hordes of other dot.coms. "A lot of people who aren't necessarily your customers need to understand your space," Thompson explains. Translation: An initial public offering looms. Therefore, he admits that part of the campaign's job is to "set a high noise level before we go into our quiet period." In early December, WebEx raised $26 million in venture backing with the express purpose of getting the word out and grabbing potential investor and customer mindshare from online meeting rivals such as Outreach Technologies' Embrace service and PlaceWare's Conference Center.

WebEx isn't some fly-by-night "content" play or iffy e-tailer. Its technology is up, running, working, and has won widespread kudos in the technical world. "Meeting online" with WebEx means individuals in a work group can not only all view the same document, photograph, or slide show, but they can take over each other's desktops and work on each others' files. The idea is to eliminate the need for travel and assembly in boring, chart-filled, mind-numbing meetings. RuPaul even used it with Thompson and his staff to remotely make edits to a WebEx press release, changing his description from "drag queen" to "towering glamazon." As Ru tells one of his commercial-mates: "Girlfriend, you could be home sippin' latte in your lingerie and still make this meetin'!"

WebEx is looking to go public within six months, acknowledges Subrah S. Iyar, a veteran of Apple Computer and Intel who is WebEx's CEO. "If we wanted to stand out, there aren't that many options," says Iyar. He concedes that "some investors were quite concerned," at the notion of RuPaul leading the way on his five-inch stilleto heels. One of them, Kip Sheeline of Summit Accelerator Fund, admits he was initially concerned, although he points out that "if this was a TV ad that just had a bunch of drones marching off a cliff like Apple did a few years ago, we wouldn't be having this conversation."

FEATHER BOAS. True, although, ironically, Thompson told me that one early idea for this spot was a remake of Apple's famous "1984" ad--except the runner would be replaced with RuPaul and instead of hurling a hammer at Big Brother's video image, he would sling a purse.

RuPaul turns out to be a very articulate and enthusiastic spokesperson who the WebEx folks say wowed investors at a campaign launch party (where blue feather boas were party favors). He's also in line for Net upside--taking cash and equity for his services.

Traditionalists charge that Internet companies are mixing up buzz with branding. Take, for example, Cyberian Outpost's spots setting a pack of wolves on a marching band, or a current campaign for, a college textbook purveyor, that features a geek screaming and cavorting with a giant banana.

Ignoring basic tenets of advertising--creating and delivering a consistent, appealing proposition to actual customers--could be dangerous. "Most Internet company ads are bewildering, annoying, and sophomoric," says New York strategic branding consultant Alan Siegel of Siegel & Gale.

Not so, says Iyar. He points to expensive but successful campaigns from such outfits as and at last year's Super Bowl. They offered witty, emotional tugs on viewers with children pondering their futures, and a security guard looking for his dream job.

Siegel has emphatically discouraged clients who have wanted to use what he calls "outrageous" celebrities, ranging from Dennis Rodman to Donald Trump. "I would have severe reservations about using a RuPaul," Siegel says, citing the Super Bowl as a venue bound to attract many people with conservative religious values, not to mention, good ol' boy football rednecks who will be offended at the whole idea of a drag queen. "When you use people who are outrageous and on the edge, you put yourself at risk."

A week after the commercial shoot, I catch up with the WebEx team back in San Jose, where they're showing a rough version of the commercial to Iyar. The spot is clever and funny--but some of RuPaul's undeniable magnetism is lost on the small screen (RuPaul accurately explained to me in Los Angeles: "You have to stand next to me to get the scale and realize how huge I am."). And if you're not already hip to Ru, I'm not sure you'll realize she's a he--and thus get the "draaag" joke. Iyar's reaction: "I think it's tastefully done. My main reaction is: Should we have bought more time?"

So, you make the call, Girlfriends: Ru and WebEx will play at the Super Bowl. But will they play at the water cooler?

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