D'Ambrosio is an odd choice. He has been a technology executive until now. He was CEO of telecom equipment company Avaya, which he left for medical reasons in 2008. Before that, he worked at IBM (IBM) for 16 years.
D'Ambrosio has been a consultant to Sears for six months, advising the board on strategic issues. Still, the selection of a technology executive as CEO is a strange one. Many people believe Sears needs a seasoned manager with a background in retail.
There is some precedent in recent years for companies looking outside their industries for CEOs. Ford (F) is the most successful example. In 2006 it brought in Boeing executive Alan Mulally and he engineered one of the great large-company turnarounds of the decade. Like Mulally, D'Ambrosio is something of a long shot. Sears is a very troubled company. The board may eventually come to regret not bringing in a seasoned executive from a firm like Macy's (M) or Walmart (WMT).