Strictly Business — Women of Influence

Karen Kaplan

C.E.Os and chairmen (or in this case, chairwomen) are notoriously busy. When we found out that Karen Kaplan from Hill Holliday was willing to give us an hour of her time, to say that we were both surprised and excited would be an understatement. The opportunity to hear about the journey of a woman who literally began as a receptionist and is now C.E.O and chairperson of a company — in an industry where only 3% of women are in a director’s role yet who are responsible for 80% of consumer spending — is a big deal.

Any lobby where they make you sign in and print out badges with your full name and picture on it also feels like a ‘big deal’. The Hill Holliday agency, which is located on the top floors of a downtown Boston skyscraper is also very impressive. As we got off the elevators, we were greeted by a kind (male) receptionist, and a breathtaking, panoramic view of the harbor and surrounding clock tower. While waiting for our appointment, we sat on comfortable couches and soaked in our surroundings.

“Law is black and white: what’s legal, what’s not legal. Advertising is all the grey area”

As Ms. Kaplan’s assistant escorted us to the conference room, we were greeted by employees impeccably delivering the HH brand experience at every touch point and every nook and cranny. Although the vibe appeared to be laid back which most certainly helps to promote and cultivate the creative ideas that make Hill Holliday one of the most reputable ad agencies in America, you also get the feeling that things most certainly get done around here. And not only just things, but important, innovative things and thought processes.

The leader behind this success, especially in a market where the invention of social media has changed how we look at and engage with advertising and media, is Karen Kaplan. She herself is stoic, with gentle sophistication that shines through in her charismatic nature. Her composure is impeccable — from the moment we came in contact with her, you know that she is the boss.

“At the time I kind of just wanted to delay the inevitable fear of ‘what are you going to do for a living?’, which resonates with a lot of people.”

Was there a pivotal moment in your life when it became clear to you that you were meant to be in the advertising industry?

Well, not really. I kind of stumbled into advertising, very happily stumbled. I thought I wanted to go to law school, which is kind of funny because now in retrospect, I think advertising and law are at 180 degrees of separation. Law is black and white: what’s legal, what’s not legal. Advertising is all the grey area. I don’t think I would have been a very happy or successful attorney. I graduated in the middle of back-to-back recessions in the early 80s. I’m not sure I wanted to be a lawyer, at the time I kind of just wanted to delay the inevitable fear of ‘what are you going to do for a living?’, which resonates with a lot of people.

I called a recruiter about a job at a law firm for which I was about 30 years shy of experience. I offered myself up anyways, and the recruiter very kindly asked if there was another industry I was interested in. I didn’t really have an answer at the time; I wasn’t very focused. There was a receptionist position available at an advertising agency that the then C.E.O, Jack Connors, had personally interviewed and rejected 40 candidates for. Since I was competitive, I wanted to see if I could get it. He was a big presence in Boston at the time, and I thought nothing bad will come from meeting him. And you know what? I got the job.

“The difference today is that people share good, bad and ugly. So it’s in your best interest to be authentic.”

Now that you have lots of different experiences under your belt, beginning as a receptionist and now serving as C.E.O, what does advertising mean to you today versus how you felt in the past?

I would say that advertising means something different not only to me, but to the entire world. Advertising used to be ‘made to be seen’. It was a TV spot, an outdoor billboard, print ad, or radio. It was made to be one-way. Now with the internet — and all digital, social and mobile platforms — advertising is now ‘made to be used’ — and that changes everything.

So what’s advertising today? Everything and here’s an example: Walmart’s positioning is “everyday low pricing.” They used to spend their advertising budgets on television ads, promoting low prices, everyday. But about a year ago, they created an app called Savings Catcher, which scans your receipt and if another store has a product you purchased at a lower price you will be credited the difference. It’s smart because people are engaging with it and with their brand, instead of just hearing about it. You’re using it versus seeing it. So everything about advertising is different now from when I started, but in a really exciting way.

In the advertising world, how do you balance selling something and remaining authentic?

Everything has to be authentic. At Hill Holliday, we spend just as much time figuring out the strategic positioning for a client as we do on the creative expression of it. So if you are creating something that is not authentic to the brand, the company, the product or the service, it not only won’t be effective, but it will be damaging to the brand’s reputation.

For example: if a laundry detergent promises a whiter white and it doesn’t deliver on that promise, your consumer will never buy it again AND they will tweet about it. The difference today is that people share the good, bad and ugly. So it’s in your best interest to be authentic. I think there’s something unique and differentiating in every brand and it’s our job to figure out what it is, and how we can creatively express it so people remember.

“I didn’t have Pinterest or Facebook growing up, but the bar to achieve these “perfect lives” people portray on social media is set so high, it’s unattainable. It’s not real.”

Do you think that your gender impacts your role as CEO, particularly in a male dominated industry?

I think everything about a person impacts the job that they do. I read somewhere that “Everyone brings their own unique set of building blocks to work, and what’s great about advertising is that you get to play with everyone else’s blocks.”

So the more diverse the background, experience, race, gender, sexual identity, geography (and the more diverse the better!) then the more interesting set of building blocks we’ll have. My building blocks have to do with the fact that I am a woman. I think every experience you’ve had has an impact on how you lead, and I think everyone leads differently. Back to your question on authenticity — I think it’s exactly the same. If you are not an authentic leader people might follow you for a little while, but you’re going to invariably say or do something that disconnects with the way you want to appear.

While I love that Sheryl Sandberg has created the Lean In platform and brought the conversation into the spotlight, I don’t necessarily buy into everything she says. I think we can “lean in” all we want, but right now, the default system of business is set for men. For example: those of you that are left-handed; it’s not easy right? You’ve got no scissors, you’re always bumping elbows into others’, you have to figure out where you are going to sit at the dinner table and you have to be strategic about it. It’s not easy. That’s kind of what it’s like to be a woman in business.

I am certainly thankful to Sheryl Sandberg for getting women’s leadership on the public agenda. And now with female Presidential candidates, it’s been one great thing after another so I’m very hopeful for the future.

As an advertising expert, how do you think women are portrayed in media?

There are so many great examples! Last week I was lucky enough to introduce Kevin Plank, the Chairman, C.E.O and founder of UnderArmour while he was speaking here in Boston. I did a lot of research on him and the work for UnderArmour, specifically with Misty Copeland, who’s an African American ballerina. There was also a great Giselle Bunchen spot. Both were really well done and empowering.

There’s also a campaign for Always, which is owned by Proctor and Gamble that I like. It started as online content, and because it got shared so much, became a national TV spot. I’m not sure they understood the power of it at first. It’s called Throw Like A Girl,” which asks young children what it means to throw like a girl.

It’s nice to see the “no makeup” trend happening in popular culture -which influences my business — like the “Dove real women” campaign. It’s fantastic! There are a bunch of examples I could point to today that are extraordinary and incredibly inspirational.

On the other hand, I’ve noticed a trend lately that people are painstakingly curating their social media lives to only show their best self — and I think that’s a really dangerous thing for young women. I didn’t have Pinterest or Facebook growing up, but the bar to achieve these “perfect lives” people portray on social media is set so high, it’s unattainable. It’s not real. It should be about making women feel good about themselves (not like a PinterestFail!). I think we’re doing a better job, because I think people are demanding it, but I think we can always do better. I still see things that make me cringe sometimes.


In an interview with Fortune, you said that,” women are in the social consciousness and are front and center now.” Having said this, what kinds of progress have women made over the years in terms of careers and lifestyle?

I don’t think there’s any job a woman couldn’t do, but I do think it could be easier. We could make it easier for women to believe they can do any job they want to do. I always joked that I’ve had the same sixteen jobs everybody else my age has had, I’ve just had them all at the same company. I raised my hand for every opportunity here and I think if you put your mind to it, and you’re confident and optimistic, I think you can do anything. I just think we could use some more examples.

There’s an expression, “If you can see it, you can be it.” I think the more people see, the more they believe they can be. I feel an obligation to make it easier for the next generation — like my own daughter and the women who work at Hill Holliday. People always say to me, “You’re such a good role model for your daughter.” I always respond, “And I hope for my son, too.” I feel like progress is being made, but slowly.

Our modern life is dependent on screens for communication, which allows us to connect faster, wherever and whenever we want to. You were at Hill Holliday through the transition from print to digital. How do you stay current with the rapid pace of technology?

It’s very challenging but also very fun. There were years where my kids were key to my technological understanding! Just yesterday we announced that we are going to spin our media department into a separate company; a different entity with the same people. It’s kind of a big, bold move that I think will help us to grow and compete in different kinds of reviews that a media agency being attached to a creative agency would not have the opportunity to compete in. Before, we were kind of siloed the way media agencies often are. There are people who buy the traditional communications: television, radio, print, outdoor, etc. Then there are people who buy digital channels. That’s how it was.

In preparation for the big move we decided to cross-train everybody. We’re going to take the digital people to learn traditional, and the traditional people to learn digital. It was smart for us, but it was also kind of a gift for our employees because they became multifaceted. It was a very interesting study in human behavior because some of the people were psyched and some were like, “I don’t want to learn that.” What’s interesting is that you may be thinking that the traditional people were the ones who were like, “I don’t want to learn that digital hocus-pocus,” but it was actually the other way around. The traditional people who may have been concerned about their skills getting dated, ate it up. There are a lot of interesting things happening in, for example, podcasts. They are really popular right now, which is interesting because that’s like the original radio. Everything is cyclical. The pendulum will swing back and forth and you just have to figure out how to ride along with it.. Don’t throw anything away because if I had all my 70’s clothes right now…! Bell-bottoms are huge this season.

I joke that I have to run home every night to watch Extra! In my job I have to stay current on music, fashion, and style since all of this impacts what we do for a living. It’s a lot easier today to stay current on everything. I actually love popular culture, it’s fun for me, but I can’t allow myself to get dated because that is your reference point. If you think about the role of music in advertising, music is so important. The next generation is embracing things that were honored by the previous generation, which is kind of a lovely thing. It’s not the attitude of it already happened so it’s no good. The internet is great for discovering. There are so many niche communities online that you never would have known about.

If you had one bit of advice to give these girls, both individually and collectively as they explore their career options and facets, what advice would you give them as someone who has done so much?

For me, and I’m not a person who regrets things, I think there’s never one way of doing things; there are always options. I’m in the “idea business” and there is an endless supply. I would say don’t edit yourself; don’t hold yourself back.

I’m iterative; I work in a very iterative way. I like feedback. I like talking to people. I let people into my ideas. I am very comfortable with sharing my vulnerabilities. Share, be open, take feedback, process it and be better. I always think you can be better and do better. The take away here is to just go in with the idea that you are good enough and that it’s good enough. Put yourself out there, share it with people who you admire and trust, and let them help you make it better but don’t, don’t, don’t edit yourself.

Over the course of my career I cannot tell you how many times I was in a meeting and I had an idea and I thought, “I’m not going to say it out loud ’cause it’s not good enough,” and then someone up the table says the same thing and I think “ugh!” but you have no one to blame but yourself. So don’t edit yourself, don’t kill your own ideas. Arianna Huffington, who I admire greatly, calls it the annoying roommate voice that lives inside of our heads. So don’t listen to the annoying roommate!

Here’s where I think women have a competitive advantage over men in business: there are fewer of us and we have a more typically interesting approach to fashion. At Hill Holliday our dress code is very interpretive; there’s no dress code. My joke is that our HR people say Karen’s one rule is “Keep the underwear under.” That’s all I ask for. Other than that, you can dress how you want here. I think women play and have fun with style more which helps us stand out. I think being a woman can be a real asset or just being different in some way.

“Strictly Business — Women of Influence Team”

Click Above to learn more about Us