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S uperlatives PEOPLE, CULTURE, TASTE, STYLE VIEW FROM THE TOP Winning Streak THIRTY-ONE YEARS AFTER JOINING HILL HOLLIDAY AS A RECEPTIONIST, KAREN KAPLAN STEPS UP TO CEO. BY SCOTT KEARNAN PHOTOGRAPHY BY KEN RICHARDSON K aren Kaplan can do (almost) anything. The newly appointed CEO of Hill Holliday can lead a Boston-based advertising giant with nearly 1,000 employees. She can close deals with the country's biggest brands, building a client roster that earns Hill Holliday $1 billion in annual billings. She can work alongside heads of state, as a chair of regional boards and a member of the Clinton Global Initiative, to build positive infrastructure for businesses and develop future leaders. But despite all her success, there is one thing, she admits, that she's still lousy at. Typing. "To this day, I still have to look at the keys when I type," laughs Kaplan, seated in her sleek, chic office perched high atop 53 State Street, where a wall of windows overlooks the Financial District and the harbor beyond. The confession seems ironic, given her history. With her May promotion from president to president and CEO, Kaplan reached the top of Hill Holliday—but only after a long climb that began 31 years ago when she joined the company as, of all the jobs for a dodgy typist, the receptionist. About a dozen increasingly prominent roles later (she saved every business card) Kaplan is in command of a corporate giant with clients that range from VH1 to Major League Baseball (the personalized baseball bat is one of her most prized possessions). Experience playing every position has turned her into an ad world MVP. "At the time, I didn't even know what was achievable," admits Kaplan, who was raised in Marblehead by a family of modest LEFT: Karen Kaplan means: two working parents, no company car or received a personalcorporate spending account. "I had no idea how ized bat when Major League Baseball high up was high up," she says. But she found out signed with Hill firsthand. And she did it the old-fashioned way, Holliday. through a relentless work ethic that made her treat every job like it was the most important one in the company. "I was the CEO of that reception desk," says Kaplan, who had no intentions of pursuing an advertising career when she interviewed for that job. She just wanted a 9 to 5 gig while studying for law school and a chance to meet legendary business mogul and Hill Holliday cofounder Jack Connors. Connors personally interviewed Kaplan after passing on 40 other candidates—and then he made an offer that changed her life and her outlook. "He said, 'Congratulations, you're the new face and voice of Hill Holliday,'" recalls Kaplan. "The way he framed it made me pause. It was important to him, and it became important to me." "I never had visions of being a CEO," explains Kaplan, who moved from receptionist to secretary, and from secretary to the company's traffic department. "One step at a time, I always took every job very seriously and did the best I could do." That model—perfectionism coupled with intense focus—is the cornerstone of her vision for Hill Holliday's future, says Kaplan. Her predecessor, Mike Sheehan (now the agency's chairman), appointed her CEO on May 13, 2013—the 10-year anniversary of his tenure and the 45th birthday of the company itself. She immediately drew up a mission statement: "To be the best creatively driven modern agency in the country." "The best, not the biggest," she emphasizes. She says that Hill Holliday, which already garners plenty of international support through its partners in IPG, the globe's third largest advertising conglomerate, isn't interested in empire building; its interest is in letting excellence organically breed success. "It's the foundation of disaster to let yourself be distracted by what you're going continued on page 60 "I always took every job very seriously and did the best I could do." BOSTONCOMMON-MAGAZINE.COM 058-060_BC_SP_VFT_Holiday_13.indd 59 59 10/31/13 4:13 PM