Pitching the unsellable

The product: Chitika
Sounds simple enough, at first: They serve Web ads.

But then it gets more complicated: People's eyes tend to glaze over when Chitika marketing director Daniel Ruby explains that his company, based in Marlborough, Mass., offers ads that are "search-targeted rather than contextual" and describes how "instead of scanning a site for what the network deems relevant terms, we advertise directly to the intent of the user."

As Ruby puts it: "Never seems to be an easy message to get across."

But push aside the technical jargon, and the product is fairly understandable. These ads look at what a customer is researching -- say, a vacation trip to Bermuda, on a search engine like Google or Bing. When the Web surfer then visits a site that uses Chitika, they see an ad for something relevant, like a cruise package. In other words, an ad that's based on their recent search history. It's kind of Big Brother-ish, but, hey, if it helps stimulate the economy...

What the experts say: "There are two types of customers for this kind of technology-heavy service," Calloway says. "The technology-savvy customers who want to know how it works -- and the guy like me who just wants to know if it works. I don't care how it works. If it does what you say it will do, then for all I care it can work because a magic wand passes over it and you say, 'Abracadabra!'"

For those customers, suggests Calloway, "Stop explaining how it works -- and just convince me that it does, in fact, work."

NEXT: If it's good enough for Europe ...