October 9, 2000

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Women In Technology
Deborah Willingham, Microsoft

By Aaron Ricadela

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n the day in February that Microsoft unveiled Windows 2000 to the world, it was clear that the high-pressure grind had begun to wear down the company's emissaries. Months of intense deadlines had taken their toll on Microsoft's executives, developers, and marketing staff as the vendor pushed its most complex software ever out the door. Now, as hordes of international media, assorted celebrities, and computer industry luminaries descended on a downtown San Francisco auditorium for the christening of Windows 2000, most company staffers looked as though they were ready to wilt. But then-marketing VP Deborah Willingham was standing tall.

"It was 18 hours of constant in-your-face," says Christine McCaffrey Trostle, a Microsoft business planning director who was present at the event. "We had cameras pointed in our face the entire time we were in San Francisco--just interview after interview. You turn around, and there's Carlos Santana standing there. Then you turn around and it's Bill Gates. Then there's a guy from Star Trek. We were all exhausted, but Deborah was still out there shaking hands, still going."

Willingham ought to be accustomed to pressure. During her seven years at Microsoft, she's helped expand the technical support and enterprise sales force from serving smaller companies and individual departments to anticipating the needs of large businesses. As VP of Windows marketing, her job was to promote the massively complex and long-overdue Windows 2000 server software to large companies more accustomed to running apps on Unix systems. Microsoft is fond of shuffling its executives into different roles every few years, and with Windows 2000 safely shipped, Willingham this year eliminated her job as part of a departmental reorganization.

In April, Microsoft CEO Steve Ballmer named Willingham VP of human resources--at a time when the company's stock had fallen precipitously in value and workers were being lured to startups or opting to take early retirement. It was a real change of pace for Willingham. "A year ago, I would never have said this would be my next job," she says. But she soon realized that the position dovetails nicely with her strengths. "I have an interest in motivating people and growing leaders," she says. "You put together a team, learn about the situation, make sure people understand the strategy, and get roadblocks out of their way. That's pretty much been my formula, and I don't stray too far from that."

Willingham quickly rallied to the challenges she faced with her new responsibilities. This spring, Microsoft granted employees new stock options designed to compensate for the company's lower market value. Ballmer, Willingham, and a Microsoft benefits manager designed the package, obtained board approval, and unveiled the move in a span of about 12 hours, according to Willingham. She also helped tailor a new benefits package that gives overworked executives more flexible vacation schedules.

"For us to compete today with dot-coms on hiring people, one of the things we need to think about is job content," she says. "Can people here get something similar to what they'd expect at a startup?"

FactFile

Title: VP of human resources at Microsoft Years at Microsoft: Seven Previous positions at Microsoft: VP of Windows marketing; VP of enterprise customer unit; VP of product support services Previous positions at other companies: Held a variety of managerial and executive jobs in hardware manufacturing and development at IBM Education: Bachelor's degree in industrial and systems engineering from Georgia Institute of Technology Personal status: Married, two children, one stepchild Hobbies: Skiing, reading, playing piano, basketball Future goals: Make sure Microsoft stays a challenging and fun place to work. No. of high-level female execs at Microsoft: Five

Though Willingham cut her high-tech teeth for 15 years at IBM before coming to Microsoft, she should know whereof she speaks--her career moves bespeak a New Economy affinity for managing at the edge of disaster. "When something was really screwed up, or had a lot of problems, I'd come in and take over," she says.

For instance, Willingham spent time as production control manager at IBM's Tucson, Ariz., manufacturing plant, heading a team that was rushing to launch a miniature tape storage cartridge--common today--to replace reel-to-reel technology that hadn't changed in decades. Gus Vassiliades, VP of quality and customer satisfaction at IBM and a storage-product executive at the time, hand-picked Willingham as his top assistant. "This was something we could sell to every major account and represented billions of dollars in revenue," he says. "It was a major breakthrough--and an area that had a lot of problems."

Willingham's job was to manage the project's operations, obtaining parts from IBM subcontractors, fixing engineering problems, and balancing manufacturing and shipping schedules to customer demand. "When we started, on a good day, we made 37," Vassiliades says of the tape cartridges. "We needed to get to about 37,000 within a year. You need to have an iron stomach."

It also doesn't hurt to be ambitious and a risk-taker, and Willingham certainly is. An Atlanta native, she went to work for IBM in San Jose, Calif., in its planning and scheduling manufacturing lines after graduating from the Georgia Institute of Technology in 1978 with a degree in industrial and systems engineering. "I did my real job in half a day, and went around to people I thought were really smart and said, 'Can I do any work for you?'"

Willingham credits part of her success to an early willingness to "take the jobs no one else wanted," which is how she gained her reputation for fixing troublesome operations. "At IBM, those weren't very popular jobs to take, because the risk of failure was high," she says. "It wasn't a place that tolerated failure very well."

Willingham didn't fail in those risky projects, but one notable speed bump in her trajectory at IBM left a lasting impression. By 1986, Willingham had the opportunity to interview for a junior-level executive job--her first at the company and a prominent career goal at the time. She was also pregnant with her and her husband's second child. "I told my hiring manager I was due in eight months, and if there's a business reason my six-week leave at the time would be a problem to let me know," she recalls. "He was very strong on me before. But then he started saying, 'I wouldn't have wanted my wife to have such a stressful job when she was pregnant,' and comments like that."

While IBM never rescinded its job offer, Willingham says she felt she wasn't wanted in the post and withdrew her candidacy. "It took me five years to get to that point, and I always felt like I was five years behind where I could have been," she says. "I'm sure that contributed to my willingness to leave."

Yet six years later, Willingham was still bleeding IBM blue, working as an executive in the group that made the company's AS/400 computers, when a former colleague began recruiting her to work at Microsoft. After repeated requests, she met with the Redmond, Wash., vendor's product-support group, not even bothering to prepare a resumé. "I wasn't really looking for a job," she says. Despite being "bowled over" by the group's enthusiasm, she turned down Microsoft's first offer. "I just couldn't get to the point where I wanted to leave IBM," she says.

A couple of months later, she reconsidered. Working at home for a month during a program in which IBM executives were made to take accrued vacation time, Willingham says she reflected on Microsoft's offer--and the opportunity to break out of hardware design and manufacturing. In addition, Microsoft's 1,500-person support group "looked like a small, entrepreneurial company" compared with IBM. In January 1993, she called back and took the job, reporting to Patty Stonesifer, now president of the Bill and Melinda Gates Foundation and for years Microsoft's lone high-level female executive. "She was a good mentor to me," Willingham says. "I'd never worked for a woman before and never had a female role model."

As HR chief, Willingham wants to be a role model, too--for all employees. But she does note that, in general, women are underrepresented in the technical field. "Let's just say this: No one has the right percentage of women in senior jobs," she says. Willingham blames, in part, the paucity of technically trained women graduating from college today. "People need the right experience to be successful," she says. "You can't say, 'I want more women at the top, so put more women at the top.' It has to start on the bench."

In the past year, Microsoft has doubled its number of women VPs and stepped up recruiting and mentoring of female staffers. For example, the company increasingly tries to expand the pool of candidates for senior jobs by opening them up to women on staff who have less managerial experience than male applicants. "We ask whether we'd be willing to take a risk on someone to grow the diversity of the team," she says. Willingham, as her career shows, is nothing if not a risk-raker.

Staffers who've worked for Willingham say she's not afraid to dive into a project's details, but knows how to blow off steam to rally the troops. Four years ago, in the midst of performing surgery on Microsoft's Enterprise Customer unit--which was taking too long to get large accounts technical support and software fixes--Willingham took her team to Santa Monica, Calif., for a two-day seminar, recalls Kevin Johnson, now Microsoft's VP of U.S. sales and service. "Rather than locking us up in a conference room in Redmond for a couple of days, we went to Santa Monica," he says, where between meetings, the employees played beach volleyball, rode bikes to Venice Beach, and "hung out in a dive bar."

Operating from the gut seems to serve Willingham well. Despite her attention to minutiae, Willingham says more women in the workforce would do well to know when to let the details go. "Men sometimes are more comfortable and confident shooting from the hip," she says. "It's terrible to generalize, but at least for the women I've met in my career, they have less self-confidence, so they tend to prepare a little more. And that takes more time. Sometimes women make it a little harder on themselves than it needs to be. I know I do that sometimes." Microsoft's employees are glad she's such a stickler.

Continue on to profile of Shaula Alexander Yemini, System Management Arts Inc.
Return to profile of Linda Stone, Microsoft

Photo by Lou Wong

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