One of the biggest challenges of working in sales within the martech industry can be simply explaining what the product you’re selling actually does. That’s not the case with Programmatic Direct Mail®. How advantageous is it to sell a product that people immediately understand?
It’s a blessing and a curse. Yes, people can grasp Programmatic Direct Mail® within 90 seconds, but within those 90 seconds there are a lot of different thoughts that can go spinning off in different directions in terms of how to actually apply it in the marketplace. So those first 90 seconds are crucial — not just in getting brands to understand broadly what we do, but also making sure that we’re transparent and ask diligent questions to conduct as much pre-qualification as possible.

What do you mean by “pre-qualification”?
We want to make sure we create a great relationship with the brands that we’re working with. So it’s basically a case of managing expectations in order to meet them. We are extremely focused as a company at being able to drive return for our brands — it’s important for us to maintain a clear vision about their specific path to success and how they can use us to the best of our ability and theirs.

What drew you to PebblePost?
By the time I got here [in June 2016] I had already been through pretty much the entire spectrum of the startup experience, from being part of an acquisition, to witnessing growth on an incredible scale, to flat out falling on my face. So I was very thorough in my due diligence when making my next move. I spoke to a lot of different CEOs and I interviewed with 20-25 different companies to try to find the best opportunity for where I was at that point. And PebblePost just seemed like a shining light.

In what way?
I liked the culture. It just stood out. And when I first heard about the idea of Programmatic Direct Mail® I said, “This just makes so much sense.” Like a lot of others I wondered why no one had thought of it before. When I pictured where that idea could go, I knew I wanted to be part of it.

You’re basically a native New Yorker, right?
Pretty much. I grew up in New City, New York — Rockland County.

But you went to school at Indiana University. How come?
My brother went to Wisconsin, so I was drawn to that Midwest, Big Ten feel. As soon as I went to visit Bloomington for a weekend, I was locked in. Beyond that, I wanted to be a sports marketing major, and that’s a very good sports marketing school. I also wanted a business background, and the Kelley School of Business is top-notch as well.

You jumped right into the deep end with your sports marketing degree, taking a job at Madison Square Garden with New York Knicks public relations. And you were there at the height of the “Linsanity” phenomenon, correct?
Yes, I was there, and it really was Linsanity. It was nuts. It was such a rush. The PR department had never fielded as many requests as they did with Jeremy Lin. We were getting requests from reporters who didn’t even cover sports, who just wanted to document that phenomenon. Usually the press just comes into the locker room after the game for interviews, but we had to set up a separate room for Jeremy because so many people were there to cover him. I’ve never seen anything like the buzz at the Garden during that time. It was fantastic.

Was it also stressful? Did your workload just go through the roof?
The amount of hours I was putting in was kind of crazy regardless, because that was also the year the NBA strike shortened the season. So once they started playing, it was 3-4 games a week. On weeks when we had all home games, we were working 18- to 19-hour days anyway, so you really can’t get much busier than that.

You also spent a few months working at NFL headquarters on Park Avenue. What was that like?
That was interesting, too, but it was more grunt work — a lot of rudimentary stuff. But it’s still a great name to add to the resume for someone who wants to work in sports, and I made some great contacts. You could go to the cafeteria for lunch and run into [NFL Commissioner] Roger Goodell there. He was a nice guy and would engage with entry-level employees like myself. That was refreshing and might surprise some people.

What made you decide to reverse fields and go from working at long-established, brand-name sports institutions to more of a startup, digital, make-it-up-as-you-go culture?
I’ve always been a huge sports fan, but I realized that I didn’t need to actually be in the industry to maintain that. Because if you’re involved in it 24/7, you don’t necessarily want to be “on” all the time. It was important for me to be able to separate the two — to be able to come home from work and watch a Mets game and talk about that when I go back to work tomorrow morning. That part of sports, that camaraderie, is important, and I wanted to preserve that. Basically, I just wanted to go back to being a typical New Yorker who enjoys sports as just one aspect of hanging out with friends and family.

When did you decide to make the transition?
I had started reading up on startups a little bit and I saw an ad in the paper for a company called Visual Revenue. That sparked my interest enough to give them a call. Their office was on the far West Side, on the same floor as the AP Newsroom at 33rd and 10th. I couldn’t even find it at first — it seemed deserted. It was so different from what I was used to. But eventually I saw a spot in the back where about 15 people were working. It was kind of intriguing, but at the same time you wonder: Is this real? So the atmosphere seemed kind of strange … although part of that might have been because I showed up at a tech startup wearing a suit. I was only about 23, and some of the people there who were my age were actually laughing, like “Look at this idiot.”

The good news is, after making an entrance like that there’s nowhere to go but up…
Yes, and long story short, I took the job and went to work for this guy named Dennis, who was a serial entrepreneur. I’ve never met a guy with so much energy and charisma in my life. He was so enthusiastic, it was infectious. And that was what I wanted. I was pretty much the office manager plus the sales assistant, doing a lot of prospecting and admin work at the same time. I was also calling on my own leads. And yes, the CEO would sometimes have to put on a suit to go pitch VCs, although he would put on a suit and literally run from our office all the way downtown. So we worked hard, we did everything right, and then we got acquired by Outbrain. It was hard work, but also a lot of fun.

So working in a startup culture can be as much fun as working in professional sports, just in a different way. What’s the most fun part of working at PebblePost?
Being able to work with the caliber of people I work with. I’m part of a great team and a great culture. The other part of that is being able to talk to the types of brands that we tend to work with — the digitally native brands, the disruptors. They’re so interesting, and the marketplace for them is constantly evolving. It’s fascinating to be able to grow with them. Coming into work every day knowing that I’ll be able to speak with them about their challenges and how we can help benefit their company — that really makes coming to work an absolute pleasure.

Free Guide:
PebblePost's Guide to Programmatic Direct Mail

Download our short guide and learn the who, what, why, and how of Programmatic Direct Mail.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.