
Flight Crew: From left, Kayak execs Jeff Rago, Derek Young, Lincoln Jackson, and Paul English | photo by Joshua Dalsimer

Kayaker-in-Chief: It's a small world, and Hafner has to search the flights for it. | photo by Joshua Dalsimer
"Kayak has gotten where it is with word of mouth, and it's growing very quickly," says Gregory Saks, general manager of Compete's travel practice. "But they have to spend money to generate a bigger audience." Kayak currently attracts about 30% as many visits as Expedia, which generated $2.7 billion in 2007. That's one reason why Kayak bought SideStep: its audience. SideStep adds another 3 million unique visitors per month to Kayak's 4.5 million.
Kayak's marketing emphasizes the ways in which it is a better search engine. It offers more alternatives, flexibility, and airlines. For instance, Kayak includes Southwest, which doesn't make its flights available to online travel agents. Hafner has experimented with TV commercials, but Kayak relies mostly on the kind of click-through advertising it sells itself. (It's a top-five buyer of travel keywords.) That's more cost effective, although it only heightens the importance of Kayak converting its own leads into leads for the airlines and then getting those consumers to start at Kayak next time. Of course, few of Kayak's users understand this process, and the site doesn't really explain it. "If customers just see us as a travel site," Hafner says, "that's fine."
After a full day of meetings, the crew usually hits the Pleasant Cafe for pitchers of beer and games of Golden Tee. Then, Hafner and Melnick climb back into the Chrysler and put on a DVD for the ride home. Tonight, it's Pulp Fiction. Something about its underdogs searching for redemption resonates.