In reaching this pinnacle, Ms. McIlwain has come full circle from her first job at Y&R, New York, as an account exec during its glory days in the late 1980s,and saw its decline in the early 1990s. If the then VP-management supervisor hadn't moved to Chicago in 1993 to run the Kraft Foods business, the "blue-collar chick" from Berwyn, Ill. "would have left" the agency altogether, the 43-year-old says. "I felt for the first time I was on my own and I could affect this thing." A year later, the entire Chicago-based portion of the Kraft account shifted to Y&R Chicago from New York.
When then President-CEO Howard Breen restructured the agency in August 1999, he saw that Ms. McIlwain had "something special" in the way she handled clients and co-workers and elevated her to exec VP-managing director.
Then the agency got another windfall, thanks in a large part to her leadership. Sears, then in a severe slump, needed a makeover, and fast. So the agency transferred the account from the New York office in June 2000.
"There was a new energy, a new vitality and a stronger relationship with the client because of her leadership," says Stephanie Kugelman, vice chairman and chief strategic officer, Y&R Advertising Worldwide, New York, who also is the managing partner on the account. In what became a shoot-out with sibling Ogilvy & Mather, which shared the account, Y&R's creative concept for the "Sears. Where else?" theme won out.
"She led the team at Y&R in helping us articulate a new brand perspective," says David Selby, senior VP-marketing at Sears.
"I like to believe that if you earn it, it's about substance, not the B.S," Ms. McIlwain says of her new-business record. Last year, she was able to tap her relationships with Philip Morris Cos.' Kraft and Miller Brewing Co. to gain a footing as a Miller roster shop for new products. Observers believe the agency could soon pick up one of the brewer's core brands.
"I view Kary as one of the top managers in the Y&R network in the world," says Mr. Breen, chairman-CEO , Y&R North America.
Ms. McIlwain is widely considered by staff and peers as a role model in balancing work and family. "I let go a lot more than I ever have and leave a lot of decisions up to a lot of people," says the mother of a kindergartner son. She's instituted a wide range of employee perks, from flex-time to surprise days off meant to help boost morale despite the economy. That's not to say it's always a cakewalk. She recalls "a big step as a leader" when six years ago she called home to say she would be late since the H&R Block pitch needed refining. When watching baby movies later she saw that her husband that night had been filming their son, Connor, and was lamenting to the baby about mommy's work. "Everyday there is a new tape like that," she says. "Everyday there are moments when it's not working but it tends to right itself by the end of the day."
Ms. McIlwain isn't ready to rest. She's in pursuit of a good financial services account. Her management goal is to keep the creative product hot but also to grow it. "The trick is not to get too greedy," she says.