Dawn Lepore, CEO, Drugstore

A new kind of CIO—a blend of business strategist and operations tinkerer—is rising to power beyond I.T.

DAWN LEPORE
CEO, Drugstore.com

Formerly: CIO, Charles Schwab & Co.
How She's Done: Drugstore.com has yet to book a profitable year. But the nine-year-old health and beauty company may finally become profitable in 2008, analysts say. If so, a lot of the credit will go to Lepore, who joined Drugstore.com in 2004 and has helped drive up the company’s average customer sale by $4, to $78 in 2005 from $74 in 2003.

Lepore, 52, evidently has the board’s confidence. In early January, it gave her a retention grant of stock options along with a $50,000 raise, to $400,000 from $350,000. The company declined requests for interviews.

Lepore, who oversaw information technology as CIO and vice chairman for 11 years at Schwab, isn’t the first former CIO to lead Drugstore.com, an Internet company created just before the dot-com bust. Her predecessor, Kal Raman, rose from Drugstore’s chief technology officer to COO to CEO during his six years there.

In remarks to financial analysts late last year, Lepore said she considers I.T. a necessary investment for her Web site. “To me, this is our store,” she said. “So, just like a brick-and-mortar store continues to invest and remodel, we have to continually add to our Web site. That’s how we continue to delight our customers. It’s important we pay attention to that.”

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