• by Catharine P. Taylor , October 1, 2010

Last April, when word first got out that iCrossing, a digital agency that made its name on search, was close to being bought by Hearst, it caused head-scratching in an industry most comfortable contemplating its belly button. Why, advertising types thought, would a digital agency sell to the company that publishes Good Housekeeping?

While one answer is that Hearst saw iCrossing as a way to better capitalize on a future when brands are publishers, another is that the move is typical of iCrossing CEO Don Scales, who has made a career out of seldom doing the obvious - and seeing that approach pay off. The agency had reportedly also talked to what can best be called some of the usual suspects - WPP, Dentsu, Aegis - but by June, the deal was done, and iCrossing, whose clients include Toyota, Travelocity, Coca-Cola and Office Depot, became an independent company within Hearst, selling for approximately $325 million.

For Scales, the deal was many steps away from what could have been his career trajectory. He received a bachelor's and a master's in Chemical Engineering from Rice University, along with a B.S. in Mathematical Physics. It's not surprising that when he was interviewing to join Agency.com early in the Oughts, the interviewer asked him, quizzically, if he ever used the chemical engineering degree. He joked that on Saturdays, he religiously checks the chemicals in his pool. (Scales also received an MBA from Harvard Business School.)

To Hearst executive vice president John Loughlin, the disparate parts of Scales' background add up. "I think that combination of analytically focused thinking and business discipline gives him an edge in a world that becomes increasingly complex and measurable," he says.

Scales first became involved in the digital world as a managing director at Igate Capital, an e-services holding company. He knew little about Web development, but became enthralled with it while interviewing at Agency.com. "It was an enlightening experience for me because it was where technology meets creative," he says. Originally North American president working out of Agency.com's Dallas office, he went on to become CEO, departing in 2006 in a dispute over the shop's future within parent Omnicom Group.

Many agency executives probably would have done the expected thing - that is, join a similar shop - and certainly never would have considered trading in digital advertising for search. But not Scales. He had developed a joking rivalry with iCrossing founder Jeff Herzog after the two had talked, unsuccessfully, about combining their companies. With Scales out of Agency, the two joined forces. "We had this vision that we would build iCrossing into the next generation aQuantive," he explains. iCrossing now has the full slate of interactive services, including Web development, social, and mobile.

But as smart and as pioneering as Scales is, Loughlin says you'd never know it - and that also has its reward. "Don does not suck the air out of the room when he walks into it," he explains. "I think that's incredibly disarming."