Receptionist to CEO, When , 53, first walked through the doors of Hill Holliday in 1982, she had no advertising experience, or even the shorthand skills to work as a secretary. The 22-year-old was placed at the front desk of the Interpublic-owned shop as a receptionist — the bottom of the agency ladder.
Her first week on the job, two mean girls who worked hidden behind the closed doors of the switchboard room wanted to make sure Kaplan knew just how low she was.
“They come on my second day, and they stand in front of my desk,” Kaplan recalled. “They’re looming over me with hands on their hips with their little headbands, and I remember they were like, ‘Just so you know, just because you’re out here and everyone can see you, you are still on the bottom of the totem pole. You are below us, you are below the guy in the mail room, you’re below the guy who delivers the packages.’”
Shocked, Kaplan looked up from her square desk phone with four Lucite buttons. “I thought to myself, ‘We’ll see about that.’”
Thirty-one years later, Kaplan was just promoted to become the CEO of that very same ad agency, which made approximately $184 million last year. She sits in an office surrounded by the spoils of the day's 19 congratulatory flower deliveries.
“It looks like a funeral home in here,” she told Business Insider. “An art director came in my office and he said, ‘There are only two times you get this many flowers, and one of them you aren’t there to enjoy it.’”
Kaplan has reached the top of the Hill Holliday totem pole. And the switchboard operators?
“One married a rich guy and the other I lost track of,” she said. “Maybe jail.”
Getting the job
Kaplan didn’t plan to go into advertising.
Graduating as a French literature major from the University of Massachusetts in 1982, an era that makes this century’s recession look like kid’s stuff, Kaplan considered going to law school.
“I moved back in [my parents'] house and was looking for any job to save money,” she said.
So a recruiter set her up with an interview with Hill Holliday president Jack Connors for a receptionist job.
“I was told two things: He had interviewed and rejected 40 candidates before me,” Kaplan said. “I wanted to get it. I’m competitive. But I also wanted to meet him,” a minor celebrity in the Boston area.
She was hired almost immediately. Connors told her, “Congratulations, you are now the face and voice of Hill Holliday.” He took the position seriously, so Kaplan did as well.
“Connors jokingly says he never paid me enough to go to law school,” Kaplan said, but really she fell in love with the job and its culture.
Apart from the occasional catty operator room girl trying to jam up her phone lines, Kaplan liked the company and position.
“I also say that my prior work experience included babysitting and waitressing, both of which came in handy,” Kaplan said, expertly deflecting questions of just how those skills were put to use.
Kaplan took advantage of the opportunities the reception desk offered: Everyone from secretaries to executives passed her desk whenever they needed the kitchen or bathroom, top clients and VIP guests made small talk as they awaited meetings, and bigwig's children and wives became phone buddies.
“I met more people that first year in town than anyone in the agency.”
The second job’s the hardest
Kaplan circa 1990s. (Photo: Hill Holliday)After a year, Kaplan threw thoughts of law school to the wayside.But getting a promotion proved difficult: Kaplan was too unqualified to be a secretary.
With no knowledge of shorthand and a complete inability to type — even in spite of enrolling in three separate courses, one in high school, the other in college, and a third at night after working the reception desk — “I just didn’t have the skills.”
In fact, Kaplan notes, “The only job that I had a hard time getting was the second.”
When an assistant spot in the traffic department opened, she grabbed it.
It came with only one dreaded task: writing and distributing a 16-page, double sided, collated traffic sheet that had to be stapled and on everyone’s desk at 8 o’clock Monday mornings.
“We had one Wang word processor (a client) on the third floor right outside my boss’s office, and I hadn’t told her I couldn’t type,” Kaplan said. “So I would come in on Saturday to type it because I didn’t want her to see it took me all day.”
She’d come back again on Sundays to photocopy.
One weekend, after fixing a jam in the copy machine, Kaplan found an “accordion shaped, burnt, toasty piece of paper that was wrapped around the drum” that would change her career trajectory.
It was a pay sheet of every single senior officer and executive at the company.
“I didn’t even know that people made six figures in the whole wide world,” she said. “I thought, ‘Wow, I could spend some time at this place.’”
Woman on the rise
Kaplan kept all of her past business cards. (Photo: Hill Holliday)From the traffic department to design to account management and beyond, Kaplan kept every business card she’s ever had. The company even had to borrow them when conducting an internal logo study.“I had the same 12 jobs that everyone has, I’ve just had them all at Hill Holliday,” Kaplan noted, which is very different from the current revolving door of ad jobs in which employees jump from agency to agency at a startling frequency.
She’s now one of the most powerful women in the advertising world.
Even though Kaplan joined after the “Mad Men” era, when Hill Holliday had female executives, there were still workplace gender divides.
“In 1984, there was a woman who was a senior and a role model of mine, and she said, if you want to get anywhere in this industry you have to go drinking with the boys,” Kaplan said. “But I didn’t do it. I was newly married. I focused on the work.”
She continued, “If I ever felt unwelcome or unappreciated I'd shift over to something else because there are plenty of options. I never felt like there was a disadvantage in any sustained way.”
Kaplan even found a way to turn the “mommy track” to her advantage.
The first Monday back after maternity leave, her son barely weaned — Hill Holliday was one of the first agencies to have its own daycare center — Kaplan was told to pack her bags and fly to a Reebok shoot in LA.
Instead, Kaplan opted to move over to become the director of the design department, figuring “it would be a little bit of a mommy track for a few years. … As it turned out I learned the most from that job because I had my own P&L [profit and loss] and learned operational skills.”
She was then promoted to managing director of the Boston office in 2001, a time in which she successfully led the company through the dot com bubble burst and the loss of a huge client, Fidelity.
Not done yet
Kaplan today. (Photo: Hill Holliday)Kaplan wasn’t surprised when she was named CEO. After 31 years, her only trajectory was to the very top.“I don't feel like I now have the title and I'll plant a flag,” Kaplan said. “Among CEOs, there are good CEOs and better CEOs.” She plans on being the latter.
This is hardly surprising considering that she has treated every position as if she were a CEO of that department.
“You can make your mark in every single job,” Kaplan said. “I still run into people today who remember me from when I was a receptionist who say, ‘You were the best damn receptionist in the history of receptionists.’”
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