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Recently named one of the top “people
to watch in international business” by Time magazine,
Maggie Sullivan Wilderotter ’77 moves to Microsoft and
begins the next phase in a stellar career.
By Maria Healy
 As a first-year student at Holy Cross, Maggie Sullivan Wilderotter ’77
was not an athlete, but she was known as an avid sports fan.
At a basketball game one night, the person slotted to do
commentary for the radio was ill. The announcer doing play-by-play
knew that Wilderotter was at the game and asked her if she’d
come up to the booth and “do color.” Though she
didn’t know what “color” was, she learned
on the job and called that night’s game with such engaging
expertise, the station manager—who heard the broadcast—issued
the call: Who is this woman?
Wilderotter went on to become a regular radio personality,
then head of radio sports for Holy Cross, doing basketball,
baseball and hockey, play-by-play and color both. In addition,
she started her own show featuring women artists, playing
their songs and doing “color” about the artists.
One could look at this creative industriousness as a template
for Maggie Wilderotter’s future after Holy Cross. “My
father set a philosophy that the sky was the limit,” she
says. Drawing on a well of self-confidence and a comfort
level for going after whatever one wants—qualities she
says her parents instilled in all four Sullivan girls—Maggie
took her economics and business administration major to task
as an executive assistant with Arizona Bank in Phoenix; she
had moved there with her husband—now of 26-years—Jay
Wilderotter, who was then in training as an Air Force jet
pilot. When the couple moved to Sacramento, Calif., Maggie
hired on with CableData, Inc., a developer of subscriber-billing
software for cable systems. Over the next 12 years, she worked
her way up to senior vice president. Along the way she gave
birth to two sons, Christopher and Daniel.
Jay, who now harvests red wine grapes and runs his own business,
Wilderotter Vineyards, is Maggie’s strongest supporter.
He took over running the household (the family now lives
in the Oakland Hills), so Maggie could ride the momentum
she was building.
Next came five years with McCaw Cellular as the president
of the California/Nevada/Hawaii region, where Wilderotter
built out and ran the cellular and paging networks. When
AT&T Wireless bought McCaw, she then worked as executive
vice president of operations, running the cellular side of
the business—and as chief executive officer of the Aviation
Communications Division for two years, bringing in 4.5 billion
dollars. She left AT&T to act as chief executive officer
of Wink Communications, a then unknown company touting brand
new technology: software that could operate in a set-top
cable box, allowing the viewer to send instructions back
to the broadcaster—what’s now known as interactive
television. Named a “modern visionary” by the Women
in Cable and Telecommunications Foundation—twice receiving
the industry’s highest honor, the National Cable Television
Association Vanguard Award—Wilderotter cultivated partnerships
with the major networks, cable, and satellite operators,
as well as major advertisers while at Wink, and, by 2004,
interactive TV may well be an operating reality in 25 million
households.
In the summer of 1998, Wink cut a deal with Microsoft, incorporating
interactive capability in future versions of Microsoft’s
WebTV, a technology connecting television, rather than computers,
to the Internet. Since WebTV was seen as Wink’s competitor,
the deal was evidence of Wilderotter’s ultimate vision
of strategic cooperation as a means to executing a good idea.
In the process, she impressed Microsoft so much they offered
her a job. As of late November, 2002, she joined the corporation
as senior vice president of business strategy.
“This is definitely more of a thinking and planning
job versus operational execution and doing,” says Wilderotter. “The
scope is business, education, government and consumers. It’s
across the board, and it’s global.” Guiding how
Microsoft features products that help students learn and
teachers teach is “one of my missions,” she says. “One
of the things I can bring to the table is the focus on education
policy. I’m very excited.”
Of her own education, Wilderotter, who is in her second
year as a member of the Board of Trustees at Holy Cross and
is chairing the Development Committee, speaks more like a
philosophy major.
“Holy Cross prepared me how to think,” she says—“how
to make decisions, how to drill down on topics, and how to
pursue excellence. It taught me how to question. One of the
classes I took freshman year was called “God Perhaps.” I
was a practicing Catholic, and Catholicism was something
you didn’t question. But even in the way the Jesuits
taught Catholicism and theology, (the idea) was to question.
And when you do question, your faith becomes stronger.”
She speaks highly of the late Dean Joe Maguire ’58
as “a great influence on challenging students to think
out of the box, to view issues from multiple perspectives.” Maguire
often had students over for dinner to talk about whatever
was on their minds—school, classes, anything going on
in society and the world. “He provided these forums
for dialogue, debate and discussion with people from all
walks of life, so you learned how to deal with diversity
as well.”
“In the business world,” Wilderotter says, “it’s
not just about the academics. It’s also about the persuasion,
the articulation of ideas, and the ability to be a good listener
and learner as well as someone who has something to add to
the debate. Communication is about having two ears and one
mouth.”
Like other alumni in the corporate world, Wilderotter confirms
that internships with companies are good preparation for
students, but she also speaks of “bringing back some
of the basics in terms of ethics and morals as critical for
developing leadership.” And she encourages “women
alumni to mentor students, to tell their stories and provide
avenues as to how to shortchange some of the trials in moving
up the ladder.”
As for her own story? The woman who rose from doing color
for Holy Cross sports radio to charting the course of business
strategy for perhaps the most influential company in the
world?
“Never forget who you are,” Wilderotter says. “I’m
a good listener, a good communicator. I’m service oriented.
I try to draw the best out of people. You can say those qualities
are feminine, but I think they make people do better than
what they would do otherwise. And I’ve tried to marry
those qualities with what it takes to be successful—being
results-oriented, doing my homework, and not shortchanging
people as being very, very important in the process.”
Maria Healy is a free-lance writer from
Northampton, Mass.
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