Hill Holliday’s New CEO Discusses Influences

Karen Kaplan embodies agency longevity

If there were an award for longevity at a single agency, Hill Holliday’s new CEO probably would win it. Karen Kaplan, named today to succeed Mike Sheehan as the top executive at the agency, joined Hill Holliday as a receptionist in 1982. Back then, the shop had 125 employees at a single office in Boston; today, the agency employs 950 staffers at offices in Boston, New York and Greenville, S.C. Total revenue, from accounts such as Dunkin’ Donuts, Bank of America and Liberty Mutual, is estimated at about $200 million. Kaplan, 53, takes the mantle nearly six years after she became U.S. president and as Hill Holliday prepares for a big presentation. The agency is partnering with fellow Interpublic Group shops Campbell Ewald and Lowe to pitch Cadillac’s creative account later this week. Kaplan took time out from pitch preparation to discuss her influences and why so few women run creative agencies these days.

What advice did [previous CEOs] Jack Connors and Mike Sheehan give you about taking the top job?

I worked for Mike for 10 years and side-by-side with Mike for 10 years before—so, 20 years (in all). And I worked for Jack for 25 years. At one point I remember looking at him, saying, “You know, I’ve been under your roof longer than I was under my parents’ roof.” So, at that point not much needs to be said. But it was always very implicit that both of them would be very happy if I found a way to honor the past and our great legacy but also drive our future.

In an industry where people move freely from agency to agency, why have you stayed put?

First of all, I have never been bored a day in my entire career. And everything I wanted to accomplish, I was allowed to accomplish here. I used to think that every company was like this. Don’t forget—I’ve never worked at another company. So, I used to think that every company was like Hill Holliday. Now I understand that it’s a very special place and it’s a very special culture. It’s a place where hard work, creativity and great ideas are recognized and rewarded no matter where they come from. And you’re allowed to grow. 

Who has had the most influence on your career?

My parents first and foremost, who were like the perfect balance. I call my mother, my "I believe in you" person. I always say everybody needs an "I believe in you" person. She always told me that I can do anything I wanted. When somebody believes in you, you believe in yourself … My father’s favorite thing was, you know, I’d run home with some accomplishment like straight As or some sports trophy and my father would look at me and say, “You know, Karen, a pat on the back is just six inches from a kick in butt.” I never understood. I always thought, well, he’s not being very supportive. But I now understand that he didn’t want me to get too accustomed to success or be too impressed with myself.

Who else?

Jack Connors obviously was a tremendous influence. His entrepreneurialism, courage, vision, ambition. A lot of people don’t know that he was 25 when the agency was founded. There were three other partners, then two, then one and then just him, but really Jack was the driving force. And then Mike [Sheehan]. Taking the baton from Jack—which I think is not easy, following a founder. And then successfully growing our business and navigating us through some of the most cultural shifting and financially demanding times that the world has ever experienced. Mike has got unbelievable instincts, perspective, his sense of humor, judgment, wisdom. Then I cannot tell you how much I learned from my clients. So, I would have to call out Anne Finucane because I used to work for her at Hill Holliday, then was her agency partner at Fleet and now, at Bank of America. She’s a friend and I’ve been following her around for literally 31 years.

How would you describe your management style?

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