Stephen Gillett was 32 years old when he took on the CIO job at Starbucks in 2008. Starbucks had gone from high-growth superstar to a company whose same-store sales were in decline--its stock price was down nearly 50% in less than two years. Gillett, with no retail experience, was now in charge of IT that supported a global supply chain and stores worldwide. The guy didn't even drink coffee until he started interviewing there.

Starbucks faced what Gillett now describes as a "technology debt." In racing to add about 2,300 stores over the previous three years, the company hadn't invested enough in in-store IT infrastructure. Its cash register system ran on DOS, so it took six weeks to train a new barista to get proficient on it. Store managers couldn't get email, because the one computer in each store processed credit cards, so it was locked down for regulatory compliance reasons. Starbucks had started work on its first global ERP system, and Gillett had to decide whether to push ahead.

Despite having all that work on his plate, Gillett made a pitch in early 2009 for even more responsibility. Howard Schultz, who returned as CEO in 2008 to turn things around, had told company executives after the 2008 holiday season to come back in the new year with some big ideas. He had urged them to think beyond their own corporate functions.