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After serving as president and chief operations officer of United Airlines, where he provided critical leadership in the initial employee-ownership period and the development of the Star Alliance network, Edwardson was tapped by CDW founder and chairman emeritus Michael Krasny to guide CDW through the tech bubble aftermath of the early 2000s.

Edwardson focused the technology provider's efforts on customer service, productivity, and market share gains and subsequently helped sales and profits climb steadily in what was otherwise a bear market for technology companies. In keeping with the employee-centered culture at CDW, Edwardson helped set the new standard for executive involvement and accountability. Despite his Fortune 100 experience, he is known for unorthodox motivational methods and an open-door management style.

Edwardson has made significant contributions as a corporate citizen, both in Chicago and internationally. While he served on several corporate and nonprofit boards, Edwardson also expanded his philanthropic mentality, garnering contributions to charitable causes from his company and employees. Highlights from 2005 alone included several CDW-sponsored relief projects to U.S. regions hit by hurricanes and Asian communities involved in the tsunami crisis.