Mad Women

Want to make it to the top of the advertising industry? No problem: Just survive a gauntlet of wage discrimination, sexism, and mommy-tracking. Here’s how three superstar Boston execs overcame the social costs of being a woman in the workplace. —By Tessa Stuart

mad women

Illustration by Gluekit

Lean in. Demand fair compensation. Don’t qualify your opinion. Don’t say sorry. Every day, women are pelted with patronizing advice about how to succeed. Studies and articles tell us what we already experience and know: Women have been chipping away at the glass ceiling for 50 years, but in fragments, not whole panes. In the business world, women represent a scant 5 percent of Fortune 1000 CEOs and hold 17 percent of board seats at Fortune 500 companies. This void of female business leaders is baffling in light of statistics that show that we excel in school, obtain more degrees than our male colleagues, make up half of the workforce, and are closing the gap in middle management. Still, we are all but eliminated from the upper echelons of industry, the pay gap persists, and the penalty for motherhood is real. It is difficult not to lose hope that women will find equality in the workforce.

But then there are those rare victors—the celebrated few who stand above the rest as models of success, the ones we can look to and think, If only I could replicate what she did. Which was why, on a wintry Wednesday evening in February, a curious crowd of students trudged through several feet of fresh snow to an auditorium at Boston University to hear from three of the most powerful women in advertising. Each is the first female to hold her high-ranking position: Kristen Cavallo, president of Mullen Lowe’s Boston office; Pam Hamlin, global president for Arnold Worldwide; and Karen Kaplan, chairman and CEO of Hill Holliday.

Between them, they’ve created and managed the images of brands such as Coca-Cola, Volkswagen, Progressive Insurance, Ocean Spray, Verizon Wireless, and Dunkin’ Donuts. As they spoke, a student jotted down notes: Karen Kaplan: “Be curious, open, and collaborative.” Pam Hamlin: “Show off a ‘make it happen’ attitude.” Kristen Cavallo: “Be opinionated, hungry, and humble.”

Inspirational? Sure. But these were broad outlines, as opposed to practical advice. That night, instead of buzzwords, it would have been valuable to hear a deeper meditation on how each woman managed to rise so high in her industry. We need specifics, guidance, and role models to help navigate the unwritten rules of business as we fend for our place on an extremely lopsided playing field. And that’s a problem for young women who are entering any profession and hoping to find mentors for their own careers.

It reminded me of something Irene Dorner, the former president and CEO of HSBC USA, had said. “The women at the top of organizations that I know will tell you that we think that we’ve made it because we were born the way we are and can play by these rules without feeling damaged by them. Or, we’ve learned how to play by these rules and use them to our own advantage,” Dorner told the New York Times in 2013. “I suspect that we were simply not very good role models, and there aren’t enough of us to be visible so that people can work out how to do what we did.”

The best guidance, then, may be not in the advice these rare victors have to give but in their stories of the pivotal moments throughout their careers, moments with which we can identify.

In public that night at BU, all three ad women offered encouraging clichés, but weeks later in private they were willing to fill in the gaps, sharing their winding and unconventional journeys to the top. In no time, one thing became clear: The women who do make it all the way to the apex of their industry have very different career trajectories than men. There may not be a list of specific rules every woman can follow, but the real-life stories of Cavallo, Hamlin, and Kaplan are illuminating—and that can make all the difference.


Kristen Cavallo was making $18,000 a year when she walked into Jim Mullen’s executive office in 1995 prepared to ask for a raise. Mullen Advertising was still a boutique agency then, though it would soon become a giant in the industry. She’d spent the past year and a half toiling as an intern and then a strategist, she recalls, and decided, “I have an MBA; I’m going to go in and negotiate my salary.”

Cavallo had started her career four years earlier with a salary of $40,000—good money for a 22-year-old in 1991—working in sales for the cosmetics company Clairol. Lured by the office’s youthful energy, she took a pay cut to accept the internship at Mullen, back when the firm was still operating out of a stately ivy-covered manor on the North Shore called Penguin Hall. From the outside, the agency looked like Downton Abbey, but inside “it was alive and vibrant and exciting,” Cavallo recalls, “and I thought: This is where I want to work.”

After proving herself as a strategist at Mullen on the BMW account, Cavallo was approached by crosstown competitor Arnold Worldwide about the possibility of switching firms to help Arnold woo Volkswagen, which was threatening to abandon the U.S. market entirely. Cavallo wanted to stay put, but she figured she could leverage the offer for a pay bump, so she marched into Mullen’s office intent on making a case for why her education warranted a larger salary.

The persistence of the pay gap is often attributed, at least in part, to women’s reluctance to negotiate their salaries. Women made 82 percent of what their male counterparts did in 2013, according to the U.S. Bureau of Labor Statistics. By asking for a raise at all, Cavallo put herself in the minority—not only of women, but of women with advanced business degrees. Only an eighth of women with MBAs attempt to negotiate their salaries, compared with half of their male counterparts.

She was in for a shock: Mullen dismissed Cavallo’s request out of hand. “If you believe that an education automatically merits you a higher salary,” she says Mullen told her, “you should go across town to Arnold, because they all graduated from Harvard.”

Deflated, she walked out of Mullen’s office and down to the agency’s parking lot, where she ran into Joe Grimaldi, Mullen’s chief operating officer at the time. Cavallo asked him what she should do: keep slaving away for the same pitiful salary, or go pitch Volkswagen for Arnold? He listened. Then he told her she should go work for the competition.

Incredibly, even now Cavallo blames herself for the negotiation blowing up in her face—she claims she hadn’t done enough research on Mullen to tailor her argument—but study after study has shown that because of her gender, Cavallo was at a disadvantage before she even walked into his office. It’s called the “social cost” of asking for a raise, and it has repeatedly been demonstrated to be higher for women than for men. Many researchers have shown that managers are less inclined to want to work with women after they’ve asked for a raise, while managers’ willingness to work with men remains largely unaffected.

What that means, in a practical sense, is that women’s failure to negotiate their salaries might not be based on an assessment of their own worth, but rather on what the Harvard Business Review dispiritingly characterizes as “an accurate read of the social environment.” Hannah Riley Bowles, who teaches business negotiation at Harvard Law School, sums it up by saying, “Women get a nervous feeling about negotiating for higher pay because they are intuiting—correctly—that self-advocating for higher pay would present a socially difficult situation for them—more so than for men.”

Now faced with a major career decision, all Cavallo remembers thinking was, Gosh, I must not be very important.


Pam Hamlin had been running a portfolio of big-name accounts at Arnold for several years when she began seriously contemplating going to Harvard Business School to get her MBA. After all, she thought, her father, a Wall Street trader, and her grandfather before him were both HBS graduates, as were many of the men at Arnold—including her mentor, Fran Kelly.

Kelly was on his way to becoming a legend in the business: He was inducted into Boston’s Ad Club Hall of Fame in 2013. And he had worked closely with Hamlin, becoming a vocal ally. She still remembers exactly what he told her when she asked for his advice about whether to return to school: “You don’t need to go to Harvard Business School,” he said. “You need to learn how to play golf.”

“What?” she replied, understandably taken aback.

“If you go to business school you’re going to take yourself out of the industry for two years,” Kelly warned, and “some of your peers will likely progress beyond you, and [a business degree is] not a requirement to grow and lead in this industry.”

Hamlin listened to Kelly’s rationale. Okay, she thought, I’ll bite: “Why should I learn how to golf?”

“There is a lot of business done on the golf course,” Kelly replied, “and you’re going to miss out on it.”

This was back in the early ’90s. Asked to elaborate on his advice today, Kelly explains that in Hamlin’s case, the cost just seemed to outweigh the benefit: She would lose two years of career progress and two years of salary before even factoring in the cost of tuition. “If you know you’re going to be working for 30 years, you don’t think about it,” Kelly says. “But if you think maybe I’m going to work for four, and then take five years off to start a family, the numbers don’t work out as well.”

Hamlin respected Kelly immensely, but questioned whether he would have given the same advice to a man. It seemed counter-intuitive. Should she really skip the prestigious degree and work on her putting, just because her career might get waylaid by a pregnancy?


Karen Kaplan is now one of Boston’s most influential women: She famously rose from receptionist to chairman and chief executive at Hill Holliday, sits on numerous boards, and once served as chair of the Greater Boston Chamber of Commerce. As a young woman, Kaplan didn’t take herself out of the workforce to have kids. When her first child was on his way, she stayed at work until the very end—the day her water broke in her office at Hill Holliday in the Hancock Tower. “And it wasn’t a trickle,” Kaplan says today, struggling to contain her laughter. “It was a bucket! By the time I got back from maternity leave, four months later, the urban legend was that a client delivered my baby on the conference room table in a meeting.”

She credits the fact that she didn’t have to take significant time off from work—time that might have meant missing the very opportunities that helped her rise in the ranks to where she is today—to an innovation introduced at Hill Holliday in the 1980s by none other than its cofounder and the most influential businessman in all of Boston, Jack Connors.

It was simple, Connors says today: “I noticed that every so often we were losing a really talented woman because she was going to have a child.” He wanted to keep those women at work, so he began kicking around the idea of creating a daycare center inside the office. At the time, he says, there were no models for such a thing anywhere in the advertising industry.

Connors can’t recall the exact numbers, but he reckons his company was losing nearly 100 percent of the women who went on maternity leave before implementing the daycare center. After it opened, he says, the firm kept nearly every one. “It really did the trick,” Connors says. “Really good people—women—stayed with us longer.” Connors cites Kaplan as proof of the program’s success: She took advantage of the daycare center in raising both her son and daughter. But while it might have seemed to Connors that on-site daycare “did the trick,” for some of the women who worked for him, like Kaplan, it created a new set of complications.

Connors’s daycare program did help bring Kaplan back to the office sooner. But she’d taken for granted the fact that her son would be nearby, so she hadn’t weaned him before she returned to work. Her son had never taken a bottle, which was a problem when she showed up at the office on her first day back from maternity leave and was told she needed to pack her bags for an overnight shoot in Los Angeles. “For the first time in my whole career I said, ‘I can’t.’ I said, ‘No,’” Kaplan remembers. “I physically couldn’t do it.”