Industry Series Vol 2.1 — James Santilli and Leo McCafferty, Pittsburgh Penguins

Jack Tipton
The Sponsorship Space
12 min readApr 3, 2018

WHERE: Red, The Steakhouse Pittsburgh, 600 Grant St, Pittsburgh, PA 15219 — redthesteakhouse.com

RECOMMENDED EATS: Steak — any steak. Filet mignon preferred. Incredible flavor finish in every bite. The house salad is top-notch, and the truffle whipped potatoes are amazing. Donut holes for dessert are a must!

Jack: Can you each define your current role? Why do you enjoy what you do?

Leo: My official title is Senior Director of Digital Marketing for the Pittsburgh Penguins. For me, marketing is about telling stories. Over the course of my career, I have told stories in many different forms. I enjoy this current role specifically because it is a new challenge for me.

It’s a growing industry, and seemingly an industry where everything is constantly changing. People are now spending most of their time in the digital space. It’s exciting that I’m helping to lead that charge for the Penguins and communicating directly with our fans. I’m helping connect our fans to our players by giving them access they can’t get anywhere else. Growing the avidity of our fan base in new and unique ways is a really rewarding experience.

James: My official title is Vice President of Marketing for the Pittsburgh Penguins. I oversee branding, advertising, video production, in-game entertainment, and social media for the organization.

What do I like most about my job? I love sports — I always have. When I was in school, I couldn’t wait to go home and either play or watch a sport. When I had a job outside of sports, I was constantly making plans to watch my favorite teams in person or with friends. I knew I needed to find a way to make my passion my profession.

For me, the ability to work in sports and introduce the sport of hockey to new fans is what keeps me driven for more. I truly enjoy doing what I do. I believe that to be a good marketer, you have to believe in your product. You have to have passion for your product. It’s a major reason why my current role is a great fit.

Jack: In my world, we typically try to define success as a revenue goal achieved. How do you (as marketers) define success? How do you evaluate your marketing efforts during a given season?

James: During my first ten years with the Penguins organization, I was in ticket sales. In those days, it was easy to understand if I had a successful day. I could run a report and instantly know if the day was successful or not based on ticket revenue generated. It was clear and evident whether you were (or are) successful in ticket sales — it was all about the numbers.

In marketing, it’s not always that cut and dry. To me, success from a marketing perspective is growing the fan base one hockey fan at a time. Success could be introducing the game of hockey to one more person. Success could be motivating someone to actually play the game of hockey. Success could be making the Penguins organization relevant year-round. There are lots of ways to evaluate our success as marketers.

Leo: Success in my past life was defined by a TV rating. It was easy to see if our show performed well. For our group, there is no clear-cut metric to define success on a day-to-day basis. I come to work each day and I try and solve one problem that I couldn’t solve yesterday.

Our world is constantly evolving. You have a to-do list that sometimes you don’t complete until the summer because there was a game last night and there’s a game tomorrow night. My focus is this — if I can do one thing today that solved a problem, that’s a successful day.

Most people that work in sports develop a love for their particular sport. To me, hockey provides a great live experience. You can hear it, you can feel it. As a marketer, if you can provide the opportunity for someone to experience the game live for the first time — that’s a success. Can you provide something unique to a loyal, diehard fan? That’s a success. If you can create interest in your sport or team — whether it’s a social post or a highlight from the game — and bring it to our fans, that’s a success.

Jack: Can you share an example of a new marketing initiative that you think was successful for the organization?

Leo: We created a feature length documentary on the history of our team, and released it during our 50th anniversary season. It was a project that James and I had previously discussed, and we wanted to find a way to make it happen. What was special about this project is that our management team allowed us to produce this documentary without cutting corners. We had the full support of the organization to make it special.

James and our team had a vision for this project that was exceptional. The staff that worked on the documentary did great work and I am immensely proud of this project. It was done really well and ultimately told a great story. Whether you’ve been a Penguins fan for five minutes or you’ve been a Penguins fan for fifty years, you likely would find something in that film resonated with you and grew your appreciation of the franchise after seeing all it had to endure.

Jack: 100% agree. It was incredible work. Many people have asked me how it was made, where they saw it, and how emotional it made them feel. Do you know of any other professional sports teams that have attempted a documentary-style project?

Leo: I can’t say for sure. I’m not aware of a team that’s produced a feature length film on its own. Other teams have worked with outside agencies or outside companies, and the leagues themselves have certainly done films or documentaries. But I don’t think a sports team has ever produced something in-house as complex and dynamic as the documentary we completed last year.

Jack: What was interesting about the documentary is that it wasn’t always the rosiest story. It was the truth. Telling the story of fifty years of the Pittsburgh Penguins organization had to be a challenge.

Leo: I think that’s a credit to the organization and our management team. A great story isn’t just a positive story. You need peaks and valleys to have a compelling story and that’s exactly what this organization has experienced during its history. If you are going to accurately tell the story of this franchise, you need to include the good and the bad.

Jack: We’ve talked about solving problems. Can you tell me about the problems and challenges you both face on a day-to-day basis?

James: All entertainment properties are competing for consumers’ leisure time. For most, life seems busier than ever. People now have less leisure time and more choices than ever before on how to spend it. We compete against any type of entertainment activity. We even compete against the decision to spend a night at home with your family. Additionally, think about the amount of information that’s available at the touch of a button via smartphones. It’s an overwhelming amount of information. How do we make sure our message is being heard? How do we make sure content is relevant and engaging? How do we get people to take action? Every industry is facing this challenge.

Years ago, the traditional marketing mix was TV, radio, print, and outdoor. Now we have over twenty different marketing mediums through which we can communicate to our fans. Should we be involved with all of these mediums? Is it too much? Are we overloading our fans? Are we reaching the right fans via the right medium? We talk about this every single day. Finding balance and communicating with our fans at the right time, in the right tone and via the proper channel is a consistent challenge for us, like so many entertainment entities who are fighting for the attention of their customers.

Leo: The exponential growth of digital and social media has far outpaced the business world. We constantly have to evaluate and balance our messaging approach. We have many obligations ranging from corporate partnerships to ticket sales to creating compelling organic content. Everyone wants to live (or message) on social media. How do we balance this effectively? This is a challenge, but it is our job to find the right solution. We are strategic in both choosing the right platform based on the content, and controlling the volume of our messaging.

The marketing landscape has shifted so drastically over the past ten years. Previously, it was only print, or TV, or radio. Digital & social media is now capturing significant attention and investment.

Our daily challenge is working well with corporate partners and internal stakeholders while still growing our brand. It is a constant evolution.

Jack: Let’s talk career path. You each have amazing roles with a prestigious professional sports organization. How did you get to where you are today? What was your big break?

James: I’ve grown up with the organization — I’ve been here over twenty years. The first ten years of my career with the team I was in a ticketing role. The second half of my career has been on the marketing side. It was the perfect situation for me. Working in ticketing allowed me to talk to fans and find out what made them tick. What made them buy a ticket? What made them leave their house and come to a game? What do they enjoy about coming to the game? What is it that they could get at a hockey game (or live sporting events) that they couldn’t get at home or a sports bar?

I had all of that knowledge working in ticketing. My big break happened ten years into my career with the team. David Morehouse (our CEO) led a brand audit of the Pittsburgh Penguins. I happened to be on a small committee representing the organization that was able to conduct focus groups, solicit surveys and engage with fans, season ticket holders and stakeholders to find out what they thought about the Penguins’ brand.

We collected information and asked the question — where do we want the Penguins brand to be in the future?

I realized the brand audit experience combined with my ticket sales background and overall passion for the game, made me a valuable contributor to not only the organization but very specifically the marketing department. At that same time, the organization created a new VP of Marketing role. I felt like I was qualified for the position and could challenge my professional development with it, so I approached David and asked to be considered for the job. I’m fortunate that it worked out so well and am grateful I have this opportunity.

Jack: When you were involved with the brand audit, were you still in a ticketing role?

James: Yes.

Jack: Someone reading this interview will be currently in a ticket sales role, but has a dream to work in marketing. What advice would you give to someone in this situation? What would be your guidance?

James: I’ve been in the sports industry a long time. Your first job in the industry is rarely ever your dream job. If you are lucky enough to get a job in sports, do that job well. Really well — to the best of your ability. However, while doing your job, talk to others in the organization. Learn every possible aspect of the organization. Don’t be afraid to let other people know that you have higher aspirations. Speak up. If an opportunity presents itself, let them know that you’re interested.

Jack: Leo, what about you? How did you get to where you are today? What was your big break?

Leo: I went to Penn State, and while I was in college I had no idea what I wanted to do for a career. I knew that I loved sports and I knew that I liked to write. Yet there I was, in the spring of my senior year, having no idea what I was going to do when I graduated.

I asked my dad for advice. He suggested writing a letter to Steve Sabol, the head of NFL Films, and so I did without any expectation of receiving a response. Several weeks later, I received my big break, a call from NFL Films. I was hired a few months later. In hindsight, sending that letter was the best thing I ever could have done, it is what got my foot in the door.

Steve Sabol wasn’t sure what he was going to do when he graduated from Colorado College, but his father (and founder of NFL Films, Ed Sabol) asked him to join the company because he said that after reviewing his grades he could see that all he was doing was playing football and watching movies, making him uniquely qualified for the job. For me, I loved sports and I loved writing. NFL Films has a hiring philosophy that places an emphasis on good writing, with the idea that they can teach a good writer to be a good editor, so I got lucky. I was hired as a seasonal employee, and eventually transitioned into a full-time position.

I was a producer at NFL Films for five years, working on everything from short vignettes to long form programming, like Hard Knocks. Coincidentally, being involved with Hard Knocks actually led me to my second big break in my career. I was living in Philadelphia, but I was interested in moving back to Pittsburgh. I was getting married in the summer of 2011 and my wife and I thought about coming back to Pittsburgh. However, I didn’t necessarily want to leave NFL Films.

Someone I knew happened to be at a dinner with David Morehouse and the discussion turned to the 24/7 Road to the Winter Classic on HBO. The format of that show was very similar to Hard Knocks, and David really enjoyed the concept. My contact mentioned knowing someone who was interested in coming back to Pittsburgh, and much like Steve Sabol, was uniquely qualified for the job. It led to a conversation where David ended up wanting to create this type of show specifically for the Penguins and produce the show in-house. The timing worked perfectly — I wanted to come home, they needed help behind the scenes and In The Room was born.

I joined the Penguins organization and I loved it. After spending four seasons exclusively working on In The Room I wanted to continue to grow and learn more about the business. I had previously talked to James and let him know that if different opportunities should arise in marketing, I would be interested. Thankfully, he trusted me to move into a more traditional marketing role, and I’ve enjoyed the experience.

Jack: I see a theme developing — you each took initiative in your career to take that next step. Looking back at your career, is there a singular accomplishment that makes you most proud?

Leo: For me, it’s the aforementioned documentary. The scope and time we spent working on the project (it took a year to complete) makes it a point of pride. We were able to secure interviews of folks from Penguins past. For example, Jack McGregor was the first-ever owner of the Penguins. No one in our current front office had ever even spoken with Mr. McGregor. We were able to track him down and he became a key piece in the documentary. We had the chance to speak with Jaromir Jagr. We were given the proper resources and therefore were able to tell the story the right way. Secondly, I feel a sense of pride and accomplishment in being a part of the creation of In The Room. It’s something that will last beyond me and it is now a part of the Penguins culture.

James: The building of the Penguins brand was a huge accomplishment. Additionally, I had a small part in the introduction of the Little Penguins Learn to Play Hockey program — a program that will last well into the future. The program idea came out of the brand study results. We realized as an organization that we had to be stewards of growing the game of hockey.

The first step was mitigating the barrier to entry for ice hockey. It’s easy to sign up for tee ball, basketball or football. At the time, it wasn’t easy to sign up for hockey. Signing up your child for hockey was a huge commitment. You had to buy all of the equipment, spend money on ice time and hope that they liked the sport. It was a big financial risk. It was also a risk that not very many parents were willing to take.

We talked to Sidney Crosby and his family about this problem. We brought the Pittsburgh Penguins Foundation into this discussion. Our partners DICK’S Sporting Goods and Reebok wanted to get involved. All parties then agreed on the concept — reducing the initial cost for parents who want their children to learn to play hockey. The Little Penguins program was born.

Children who signed up for the program were fitted with head-to-toe hockey equipment (including skates) free of charge. The only expense for the participating parents would be the ice time. Because of this program, in the past ten years, we introduced almost 10,000 kids to the game of hockey.

Our Mid-Am district is one of the fastest growing district in the United States for youth hockey. We achieved our short term goal. The program was so successful that the NHL took notice. The league adopted our model and has now rolled it out to all thirty-one teams over the past few years.

I’m really proud to be associated with this program because it is helping to grow the game of hockey all across North America.

VOLUME 2.2 COMING SOON!

--

--