CIO to CEO: 56 Moving Up The Ladder

Next page: Mark Cameron, COO, VantageMed

Mark Cameron, COO, VantageMed

MARK CAMERON
COO, VantageMed

Formerly: CIO, VantageMed
How He's Done: Cameron, 51, joined VantageMed as CIO in early 2005, and three months later was promoted to chief operating officer. He still oversees internal information technology at the health-care software vendor, as well as product development and customer services. It's a big job, especially in a turnaround situation.

VantageMed had purchased 26 companies from its inception in 1995 to 1999, "but did a poor job of integrating them," Cameron says. "There were a number of areas where we were spending too much money. We had to figure out how to best apply resources and where we didn't need resources."

The "we" refers to Cameron and VantageMed chief executive Steve Curd. The two have worked together for 20 years, starting in I.T. at American Airlines in the 1980s. They also teamed up in the late 1990s at HealtheonWebMD, where Curd was COO and Cameron oversaw technical services. Three months after Curd took over as CEO of VantageMed, he coaxed Cameron aboard.

Cameron and Curd combed VantageMed's product line, looking to kill unprofitable software and services. They culled products built on older server technologies, for example, and reduced the line to Windows-only software. In 2005, the last full fiscal year reported, gross margins on software topped 63%, up from 49% in 2004.

Yet, VantageMed is still looking for its first profitable year. "We took it on to turn it around," Cameron says. "We've got everything positioned properly. Now, we'll do what we need to grow."

Next page: Dawn Lepore, CEO, Drugstore.com

Dawn Lepore, CEO, Drugstore

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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.”

Next page: Lloyd Devaux, COO, BankAtlantic

Lloyd Devaux, COO, BankAtlantic

LLOYD DEVAUX
COO, BankAtlantic

Formerly: CIO, BankAtlantic
How He's Done: DeVaux, 54, has planned his career with care. He took his bachelor’s in electrical engineering to the oil business, where he worked in computer exploration of oil fields. Next was IBM, where he scoped custom applications for clients for six years. Along the way, he got an M.B.A., thinking the finance skills would enhance his value.

During his seven-year stint as CIO of Union Planters, a Memphis, Tenn.-based bank, DeVaux fashioned himself as a consultant, talking with loan managers, retail bankers and other operating groups about their plans and how he could help with technology. When he moved to BankAtlantic in 2001, he says, he came with the understanding, though no guarantee, that the COO position would be his to earn.

“After you move from a pure technology CIO to a tech-business bridge, the next logical step is to move over to the business side,” he says. Now, with more than two years in as COO, CEO is his next goal. But he’s cautious, saying he needs several more years leading operations before he can feel ready to make the leap.

To other tech executives who want to climb, he advises picking up profit-and-loss responsibilities at some point, to demonstrate that you can be accountable for results. Also, cultivate a successor for your current job, so when upper management looks at you for a promotion, DeVaux says,“They can say, ‘He’s ready and now’s the time.’”

Next page: Maynard Webb, CEO, LiveOps

Maynard Webb, CEO, LiveOps

MAYNARD WEBB
CEO, LiveOps

Formerly: CIO, Gateway; COO, eBay
How He's Done: He’s a freshly minted CEO, joining LiveOps in December, but Webb, 51, doesn’t plan to change much about his management style or view of business. Webb has a long history as a CIO, having held the job at Bay Networks and Gateway. He led the technology division of eBay for three years, and then managed operations there for four more.

“I don’t think people saw me as only the tech guy,” he says. “One thing I’ve worked with my teams on—and I’ve said this here already—is, how do I make sure no one in the same circumstance with the same dollars can do it better?”

That outlook meshes well with the core concept behind LiveOps, a venture-funded callcenter hosting company in Palo Alto, Calif. LiveOps provides customer support operations to companies, using 9,000 agents who work at home, connected via the Internet. The company trumpets itself as a domestic, reasonably priced alternative to outsourcing call-center operations to India.

That mandate calls for ruthless efficiency. As Webb puts it, “I’m a huge fan of making and keeping aggressive commitments.”

Webb says his technology background makes him more understanding than the average CEO of the struggles I.T. faces to deliver projects. “But,” he adds, “I’m probably scarier as their boss because in many cases I’ve done their job and done it at scale, and I’m not interested in not having it done well at this scale.”