CEO, Hewlett-Packard
In 1998, when Fortune started the Most Powerful Women list, Fiorina took first place - as she did for the next five years. A star at AT&T, she led the IPO - then the biggest in history - that spun off Lucent, and became group president of a $19 billion division.
Fiorina was on track to run Lucent herself when Hewlett-Packard came calling. She became CEO of the legendary company in July 1999 and chairman the following year. Fiorina made herself the face of HP, and put herself front and center in the effort to sell to shareholders the idea of acquiring Compaq. She won that battle, pushing the deal through in 2002, but she lost the war. The merger hit rough patches, and in February 2005, Fortune's Carol Loomis concluded in a cover story that "Carly's Big Bet is Failing."
That same month, the board asked her to leave. In her 2007 book, "Tough Choices," Fiorina defends the Compaq strategy, and in fact, an energized HP seems happy to have it in its portfolio.
If Fiorina's legacy at HP is ambiguous, her status as a pioneer is not. Fiorina was not only the first woman to be hired to run a Fortune 50 company - but the first one to be fired from the job, too.