Industry Series 2.2 — James Santilli & Leo McCafferty, Pittsburgh Penguins

Jack Tipton
The Sponsorship Space
9 min readApr 10, 2018

Jack: Let’s flip the script and talk about failure. Is there a failure in your career that is top of mind?

James: A failure in my career actually happened before I started with the Penguins, but looking back it turned into a positive for me. When I was in college, I knew I loved sports and loved marketing, but I just didn’t put those two together in time!

When I graduated, my first job was in the automotive industry. I quickly knew it wasn’t for me. All I could think about was sports — not my automotive job. I needed to find a job that would combine sports and marketing.

At the time, I had heard that the Penguins were hiring. I applied and went through a long interview process. I had sessions of interviews. In fact, I interviewed seven different times as part of this process — and unfortunately, I didn’t get the job.

I asked the question to myself — what’s next? I looked for the next available job in marketing and realized I really wanted a sports marketing job. I had a bachelor’s degree, master’s degree, and one year of business experience. I decided to take a job at a sports telemarketing firm for minimum wage. I wanted to make sure I had sports experience, as I felt that was what I had lacked during the interview process with the Penguins.

I took the minimum wage job. I put all of my time and effort into being successful at this job. Within a month, I was promoted to the night manager. After a few more months, I was promoted to the sports manager.

While I was getting promoted in this company, I was sending the letters to the President of the Penguins once a month. I kept him updated on what I was doing and my progress inside the company. After five months of writing letters, the Penguins called. They were thinking about starting an inside sales department for the Penguins, and they were interested in me managing this new department.

Ultimately, I entered the organization as a mid-level manager. I had the chance to pick my staff and grow the department. Getting rejected from the first interview process with the Penguins was a short term failure, but it ended up setting me up for long term success.

Leo: My failure has a similar theme. It taught me a good lesson. I had an idea that I wanted someone to help recreate a vision I had in my head — a scripted take on reality.

On paper this was a pretty good idea, key being ‘on paper’ and the individual who reviewed the pitch was very respectful, however politely declined. I was disappointed but it wasn’t that big of a deal.

Until I found out later that I didn’t take the right approach with my pitch. I didn’t go through the right channels. I was trying to portray something in a fictionalized way on a subject that didn’t need dramatized. I was trying to take a story and romanticize it, which sometimes isn’t necessary.

I learned from that experience two things: one, it wasn’t my place to pitch this idea and two, sometimes the most compelling story is nonfiction. It was a reminder that our job is to capture the real story as it unfolds, that is the beauty of sports.

Jack: You both get pitched by vendors all the time. How do you decide who gets your time and who doesn’t?

Leo: Yes, I receive an influx of pitches, emails and phone calls. I rely on recommendations from people I know and trust. When I get a recommendation from someone I know, and they say “this group did a good job for us because of X, Y, and Z”, then I’ll listen.

Sometimes we are seeking something specific and I am actively trying to find a vendor. The most successful pitch to me from a vendor was someone who was recommended, where I had a contact that could vouch for them based on personal experience.

James: I also receive inbound calls & emails for products or services. I like to ask lots of questions. Is it a product we need? Is it different than anything out there on the market? Is it going to help us connect with our fans? Will it help us drive revenue? If the answer is yes to these questions, then we usually have an interest in further discussions. We look for references from people we know and trust — it matters.

It can be difficult for us to distinguish between all the companies that pitch us — they all seem similar. One success we had with a vendor is our story with a local company; YinzCam. We started with YinzCam roughly ten years ago — back when Mellon Arena was in existence.

They came to us as a spin-off out of Carnegie Mellon through the Pittsburgh Tech Council. At the time, we were building a new arena. We worked with the Pittsburgh Tech Council to connect us with local tech companies that thought they could help us with our new building.

We met YinzCam and immediately knew that they were talented. They indicated that they were willing to listen to our needs to customize their technology for our purposes.

We ended up working with YinzCam to become one of the first teams in professional sports to have our own mobile app. We were YinzCam’s first client in sports. Today, YinzCam is now working with over one-hundred twenty professional sports teams.

Because of YinzCam’s success with the Penguins, I’m on calls seemingly every two weeks with another team to answer questions about YinzCam. These teams want to know that they are dealing with a proven vendor that can deliver, and our relationship with YinzCam has been a success.

Jack: Is there a parallel marketing department in sports that you admire?

James: A fellow local team — the Pittsburgh Pirates. It’s a different type of marketing, but I admire them for having to market eighty-one different home games. They have been really creative — Pup Night, Yoga Night, concerts, and fireworks. I admire their creativity and hard work as a marketing department.

Leo: There’s not a specific team that sticks out to me, but there are certain types of situations in professional sports that I admire from a marketing standpoint. One such situation is being a marketer on a team that is struggling. How do you stay relevant? How do you find a way to get people to attend the games? How do you keep people engaged with your organization?

We all know sports are cyclical in nature. At some point, your team will be at the bottom of the league and if you’re lucky, your team will eventually be a contender. We always keep the cyclical nature of sports in mind. David Morehouse, James and the rest of our management team always stress that we can’t rest on our laurels just because we have a great product on the ice.

Jack: When you evaluate your current marketing mix, where is the majority of your budget being spent? Why?

James: We are moving more dollars to digital every year. It’s where our fans live. We have over five million people following us on social media platforms. In addition to those five million followers on social media, we have well over one million downloads of our official app. We feel we can effectively target current fans and potential fans through digital & social media.

However, we will not abandon traditional media — radio, TV, print. There is a segment of our fans that don’t use social media platforms, or don’t have the Penguins app on their phone. We still have to reach that segment.

We constantly weigh our options. Does this promotion merit a TV commercial and six week ad buy? Or do we simply use a push notification and send a 140-character message to 600,000+ people in five seconds?

Leo: Spending is much more fragmented than it used to be. Ten years ago I wasn’t working in marketing, but at that time most marketers spent money on print, TV, radio, and outdoor. That was the extent of it. Today, your options as a marketer are essentially endless.

We really try to balance spending dollars in new platforms that have upside, while still utilizing traditional media.

Jack: What do you think the future of sports marketing looks like?

Leo: In our world, change happens so quickly. I’m more concerned about what we will be doing in three months as opposed to years into the future. The most important thing we can do is stay on top of trends. Social media algorithms seem to change constantly.

We have to continue to understand the digital consumer. How do they consume information? What are their behaviors? What drives them to purchase? What creates engagement?

I’m not smart enough to know where the industry will move in the future. My focus is understanding the short-term exceptionally well, so we can adapt with the industry as it evolves.

James: I think the future of sports marketing is understanding the changing consumer. You hear a lot about millennials and Gen Z, but to me, just as important, is the smartphone.

Everyone has a super computer in their pocket. Everyone can access endless information on demand. If you are shopping, you can do a product price comparison across the world in thirty seconds on your smartphone. AND you can do this while sitting in your favorite recliner in your own home.

How does this change marketing? We already see the effects in the secondary ticket market.

Years ago, if you wanted to buy a ticket to a Penguins game, you had the following options:

· Call the organization directly via the telephone

· Physically head to the box office

· Contact Ticketmaster directly

Today, the secondary market for tickets to any event is robust. You can buy Penguins tickets in many different ways, and therefore we have be constantly adapting to our changing consumer.

Jack: You both have mentioned adapting to change, and I can sense its importance for your department. Expand on that perspective — why is it so important?

James: We talked about the brand earlier in our conversation, but I feel it’s important to go back to the foundation of the brand to answer your question.

Coming out of the brand study, we developed brand guidelines and a desired target demographic. We learned a lot about our organization through the lens of our fans. We learned that we had a younger demographic. The Pittsburgh Penguins were their team. The younger demographic could be considered “new Pittsburgh” — they were connected to the innovation happening in the city with healthcare, robotics, and tech. We wanted to be the team for today’s Pittsburgh, and started targeting the younger demographic.

This demo lives their lives at a fast pace. They are about instant gratification — in hand and on demand. We approach marketing the same way. We want to be the organization that’s introducing something new and unique to our fans. We want to have awareness of new technologies and social media platforms. We evaluate new technologies, see what’s happening in the industry and then we move. We experiment and we learn. It is part of our brand’s DNA.

Jack: What advice would you give to the new graduate out of college? What advice would you give to your past self?

Leo: Never be afraid to take a chance. If you don’t ask the question, then the answer is going to be a no.

You need to believe in yourself. If you know what you want to achieve in your career, be willing to do what it takes to get there.

Your first job in sports is not going to be as general manager of a team. That will also never be your job if you don’t get your foot in the door.

Don’t be afraid to talk to people. Our executive management team encourages Penguins employees to come in and talk to them — they have an open door policy. Executive teams have years of experience and young employees can learn so much simply by asking questions.

Find a company where you want to work. Write a letter to the person in charge. Don’t just look online for jobs and apply with your resume. You are likely not going to stand out. You need to find a way to distinguish yourself from the rest of the crowd.

You may be a well-qualified, well-educated and intelligent job candidate, but there are a lot of those; it’s a competitive industry so be different from the next person. Don’t be afraid to stand up and introduce yourself.

James: For a recent college graduate, the education you received is just the beginning. Start with an entry-level job somewhere. Do that job to the best of your ability. Learn as much as you can about the organization. Have your eye on that next step.

Don’t be afraid to do the extra work it takes to be noticed. Don’t be afraid to approach someone and ask them and tell them about your future intentions. Don’t be narrow-minded because your first job isn’t your dream job.

You may not even know what your dream job is. You may fall into your dream job. Stay open-minded and work hard every day.

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