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Two-Way Street: Kerry Guard's Story Part 1

Kerry Guard • March 26, 2022 • 8 minutes to read

Told from the perspective of our co-founder and CEO, Kerry Guard.

This first chapter is a three part blog series, or your welcome to download the whole chapter and read it as a PDF.

The background

I host Tea Time For Tech Marketing Leaders and the very first question I ask is, "What's your story?" I ask this question because when someone asked people around my age what we wanted to be when we grew up, it was ballet dancer, astronaut, teacher, doctor.

The answer was not a marketing leader.

The journey for each of us into advertising and marketing is unique and not always what we planned. At least, not what I planned.

I studied photography at Drexel University and received a Bachelor's of Science Degree. I chose Drexel because of the science degree. I also chose Drexel because as part of their program, I got to intern for 6 months in New York City at DKNY.

From that point on, I knew I wanted to work and live in New York come hell or high water.

I got my wish, which was both hellish and high.

Because I wanted to work in New York no matter what, the job I got wasn't important. I just needed health insurance and a paycheck to cover my rent and school payments, which were looming. Enter Uncle Sean. To me, Uncle Sean was larger than life. He was tall, thin, and bald with a goatee, wearing super cool glasses and always a button-up shirt with some funky design. Uncle Sean was living my dream of working in New York.

The summer after I graduated from Drexel, Uncle Sean was working at People magazine. He told me he could drop my resume to a few big advertising agencies where I could get an entry-level position as a media planner.

His caveat: “I can get you a media planning job, but you’re not allowed to like it because you’re going to be a photographer.”

Yes, of course, Uncle Sean. Photographer. 10-4.

My student loan payments were getting closer... and closer. With the pressure on, I got the call. It was from Universal McCann. One of the biggest advertising agencies in New York. The first season of Mad Men big. After a pre-interview with HR, they asked me to come in person to interview with a team.

I headed to New York City for the day. I stepped off the train at Penn Station dressed in DKNY head to toe. I walked across town to 3rd Avenue and up to 42nd street. As I passed through the revolving doors I entered a lobby that felt a mile high. There were three elevator banks–one bank for every 10 floors. The receptionist pointed to the second elevator bank where I took the elevator to the 18th floor, then sat down on an L-shaped sofa in a very understated lobby... and waited... and waited.

The interview

My very first interview was with Natan Cohen. Natan walked straight up to me. He shook my hand then turned on his heels and led the way. He walked me through a maze of gray partitions and overhead lights. We sat in his windowless office, where he leaned back and very casually asked, "Do you know what media planning is?"

Oh gosh... Do I lie? How could I? I wouldn't even know what to say! So I went with honesty. "I do not. What is it?"

"When you watch TV and see commercials, or see billboards or ads in a magazine, someone has to put those there."


I went on to meet two other supervisors that day, finding ways to connect along the way. Evan had a Heroes poster in his cubicle, so we chatted about the show. He had a graphic design degree so we leaned into our interests and didn't talk much about media planning.

Somehow, I got the job.

They hired five of us. All girls, all straight out of college. It had been quite the boys club before we showed up, with one female supervisor holding down the fort and paving the way for us.

The fail

Natan, my supervisor Chris, and me were in Natan's office on speakerphone. Remember those days? Years before video conferencing. We sent the client the PDF over email, then walked them through the presentation over the phone. I didn't need to see the client's faces to know they were frustrated and disappointed. Their endless questions and inflections in their voices spoke volumes. Our strategy had holes and wasn't sound.

The presentation tanked.

I’m not sure of all the decisions that happened behind the scenes, but one day I was reporting to Evan on the Verizon FIOS account then I was reporting to Natan on Verizon Wireless. I had a lot of respect for Natan. He stood unwaveringly in his convictions. As a practicing Jewish man who wears a yarmulke when publishers would take us out to lunch, if the restaurant wasn’t Kosher he would just have a drink. He hired an awesome team. All of us gelled as a single unit. We knew how to give clear feedback and how to take it. There were clear systems and processes for everything we did.

We used these MASSIVE budget sheets that needed updating the first of every month. They tracked how many TV slots we bought on behalf of our client and we had to reconcile them each month. Every time we moved slots around, we couldn’t just change the number; we had to reapportion it, deleting some from one cell then adding it into where it needed to go, then make notes as to what moved and why.

So when this presentation tanked, I felt like such a failure. Natan was always setting us up for success. We knew how to be successful, thanks to the clear systems and processes we followed. So this failure was completely on me and Chris. No excuse. I remember feeling frustrated through the whole process and knowing that we were presenting a flop, but as an assistant I didn’t have the vocabulary or know-how to fix it.

I stayed late that night to dig through magazines for a different project that was due the next day. I kept playing the presentation over and over in my head, trying to figure out where things went wrong.

Natan was still at the office. I went down to talk through what happened and how I could have done better. I plopped down in the chair across from his desk and started crying. I felt like such a failure. I failed my supervisor. I failed the clients. I'm type A - "A" as in the grade. I've never received such a big fat "F" before.

Natan took ownership. He saw that Chris wasn't using the whole team structure. Chris was a supervisor working directly with an assistant. There should have been a Senior Planner to support us both. Natan wanted to see how this situation panned out. He knew Chris would learn better if Natan gave him the space to learn and fail.

I exhaled so big you would have thought the big bad wolf was trying to blow the house down. What a relief. And yes, I had just cried in my boss's office. Blurry-eyed and red in the face, I thanked Natan for the context and quickly exited stage left to get those magazine examples he asked for.

Needless to say, that supervisor ensured he had a senior and assistant on his projects moving forward.

The promotion - kind of

On my very first day at Universal McCann, I remember taking the elevator to the 18th floor with my HR person. He was this lovely Black man in a pressed suit and tie with a thoughtful demeanor. He felt very tall in that elevator. I remember him saying to me, “You look nervous. But not in a good way. In an excited way. I hope you have a great first day.”

We got off the elevator and he handed me off to Evan, who walked me up a flight of stairs to the 19th floor. When I walked into the room, there were four desks about five feet apart facing the wall. The two other girls in the room faced away from each other. The room was big and windowless. A bookcase at the back was filled with magazines.

As assistants, we didn’t work together that much. It took us months before we even broke down barriers and talked to each other. We did become acquaintances and mostly all got along, but once we were promoted we didn’t stay in touch much after that.

Because all four assistants started around the same time, we were all up for promotions exactly a year later. There were two open spots on the Verizon Wireless team. I wanted to stay with this team so badly. They were an awesome crew and I had some close friendships and connections with the seniors and supervisors.

Natan called me into his office. I sat down in that chair where I sat many times before–my interview, presentations, brainstorm sessions, status meetings, my annual review, being berated on how to tip the delivery guy.

I didn't need to sit for long.

It wasn't me.

When Natan explained why it wasn’t me, I was sad but thankful. The way he described Jamie and Kim in terms of who he was looking for, I knew that I was neither detail-oriented nor a “machine.” Nonetheless, this was a rejection. I didn’t let it define me or own me. I simply looked ahead.

I went on to work with a gal on the Bacardi team. She moved up to supervisor and I came on as her planner. She was lovely. She took her work seriously and professionally. She had high standards. Like when I sent Excel sheets to a client, I had to save the sheet with the top left cell highlighted so when the client opened the sheet the cursor was out of the way. This detail was nit- picky, but I appreciated it.

Unfortunately, I didn't enjoy the work. It was very narrow. Presentations were templatized and didn't require a lot of strategy or thinking. There weren't many puzzles to solve, nor was the work creative.

Keep following my journey to part two of three.

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