Jason Masherah Of Upper Deck: “It’s easy to become a linear or logical thinker — but maintaining creativity is key when remaining innovative in your industry”

It’s easy to become a linear or logical thinker — but maintaining creativity is key when remaining innovative in your industry. We should ban the phrase “this is the way we’ve always done it,” so we’re never discouraging any new ideas. Jason Masherah oversees all day-to-day operations as President of Upper Deck, the premier worldwide sports, gaming, and […]

Thrive invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive or its employees. More information on our Community guidelines is available here.

It’s easy to become a linear or logical thinker — but maintaining creativity is key when remaining innovative in your industry. We should ban the phrase “this is the way we’ve always done it,” so we’re never discouraging any new ideas.


Jason Masherah oversees all day-to-day operations as President of Upper Deck, the premier worldwide sports, gaming, and entertainment company. As part of his day-to-day duties, he is personally responsible for exclusive agreements with Upper Deck’s lineup of corporate partners, licensors and superstar athletes, including Michael Jordan, Tiger Woods, LeBron James, Wayne Gretzky, Marvel, Disney, 20th Century Fox, Tim Hortons, NHL, NHL Players’ Association, NBA and more. Mr. Masherah was also responsible for the revitalization of Upper Deck Authenticated’s memorabilia division and the Fleer/Skybox brands, as well as the first tokenized sports collectibles that the company released in 2011.

Prior to his appointment as President in 2013, Mr. Masherah served as Vice President of Marketing and Business Development at Upper Deck. Mr. Masherah has been personally credited for several core programs at Upper Deck, ranging from the Yankee Stadium Legacy program in 2008 to the Evolution video cards in 2011 to the launch launching Upper Deck e-Pack, the robust online platform that allows collectors to buy, open, collect, store and trade physical cards and collectibles from anywhere in the world

Before his involvement with Upper Deck, Mr. Masherah worked for professional sports teams in various roles, including the Cincinnati Bengals and Atlanta Braves. He earned his Master of Business Administration degree from the Kelley School of Business at Indiana University and his undergraduate degree in Marketing from the Eli Broad School of Business at Michigan State University. Mr. Masherah currently resides in the greater San Diego area with his wife and children.


Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve been an avid trading card collector since I was a young kid. I started to work at a card store when I was 14, and then I opened my own card store at age 16. I was always active in the hobby of collecting cards and sports memorabilia. After college, I had all intent to work in the sports field, and I was lucky enough to meet the right people within the trading card industry, which then introduced me to Upper Deck.

Can you share a story about the funniest mistake you made when you were first starting out? Can you tell us what lessons or ‘takeaways’ you may have learned from that?

When I was first trying to get into the sports field after college, I had an interview with a Vice President of Marketing at a sports team, and he asked me what I envisioned for my career. I said I wanted to be in marketing — and he replied, “What does that even mean?”

It was a moment of reflection for me — where I had to pause and really think about my goals, and what my focus was in marketing. I think young professionals today need to take a moment to put things into perspective and understand your passion and interests.

Fast forward to when I first applied to Upper Deck, I had gone through a rigorous interview process including ten rounds and three months of interviews. I had to really persevere, so I was thrilled when I finally received an offer and was able to kick start my career.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When Upper Deck was developed, what was its vision, what was its purpose?

There were three core pillars of Upper Deck’s purpose when it was first developed.

  1. Authenticity: Providing the end consumer with unquestionably authentic collectibles during a period of increased forgeries among users in the market.
  2. High Quality: Our priority has always been to provide high quality cards, collectibles and memorabilia to fans and collectors. At the time Upper Deck was founded, trading cards were relatively bland, and Upper Deck’s goal was to disrupt the industry by creating unique and next-level products for sports collectors.
  3. Innovation: Upper Deck’s vision is to be the gold standard in the industry when it comes to innovation. As the first trading card company to create game-used memorabilia cards, autograph cards, booklet cards, loot cards, letterman cards and more, we continue innovating ourselves, whether it be through the technology of the cards, the protection of products, presentation of the trading cards, the exclusivity, etc.

Are you working on any new, exciting projects now? How do you think that project will benefit consumers?

We’re constantly innovating our products, and brainstorming ways to interact with new and existing collectors as the industry continues to experience a renaissance period. Our trading card platform, Upper Deck e-Pack®, launched in 2016, allowing users to instantly purchase and open packs online at any time, from anywhere. The e-Pack technology also offers the unique ability to bridge virtual and physical worlds by allowing users to have physical versions of digital cards mailed out at any time. We’re continuing to update the platform with our Game Dated Moments, which highlights some of the most memorable moments in sports throughout the entire year.

Additionally, we have some exciting collaborations that just launched, including a new 100-card set that chronicles “Space Jam: A New Legacy.” The set will include sketch cards of the film characters and rare autographs from the cast members, including one of the NBA’s greatest names, LeBron James.

We’ve also recently announced Upper Deck’s investment in Spry, a third-party technical solution explicitly developed to help collegiate compliance directors, athletic department staff and student-athletes navigate the Name, Image, Likeness (NIL) landscape. Spry is a one-step tool that allows student-athletes to disclose business opportunities in a transparent way to help their institution comply with NIL regulations, and we’re thrilled to support Spry as they transform the collegiate arm of the industry.

Can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

Digital Transformation is when businesses adopt the use of digital technology to transform their service or product. In our industry, digital transformation is typically viewed as digital collectibles.

The biggest challenge in digital transformation is to not utilize it linearly, as if it’s a one-way street. Around 2010, many companies started to create digital collectible apps, but for Upper Deck, we’ve always approached digital transformation a bit differently by looking at it from multiple angles and perspectives, and thinking more long-term.

Which companies can most benefit from a Digital Transformation?

All companies can benefit from a digital transformation. Especially throughout the pandemic, companies were challenged to find efficient, safe, and contactless ways to interact with end users.

For Upper Deck, we were able to elevate our digital technology to deliver even more digital collectibles through e-Pack to users around the world. It’s not about reinventing products, but more so about delivering products in a more efficient and innovative way.

Beyond e-Pack, even the trading card shops that we work with have been able to utilize social media to build relationships with consumers, and they used digital technology to promote themselves and their curbside pickup options.

In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

With Upper Deck e-Pack, we have direct connection with the consumers, which also means we’re able to easily see their feedback. We’re able to receive real-time feedback on cards that consumers are excited about and eager to purchase. The benefit here is that we’re able to apply this feedback and customer experience to our future programs and launches, helping us to navigate what’s trending and in demand for our community.

Another unique detail of the e-Pack platform is the ability to reward consumers after they achieve certain levels, gamifying the platform to create even more interaction with consumers. They’re now being rewarded for collecting sets and they’ll receive something exclusive and special in return.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

Digital transformation has historically been a very linear thing for businesses. As a resolution, you’ll need to think long-term and beyond the immediate problem solver of digital technology. It’s important to focus on how that transformation can affect your products, your customers, and your infrastructure.

Based on your experience and success, what are some ways a company can use digital transformation to take it to the next level?

  • Social Media: Engaging in the social space is key in today’s world. It creates the opportunity to receive real-time feedback direct from the consumer, for better or for worse. Social media has become the primary go-to for customer service.
  • Distribution: Using digital technology to elevate how businesses provide their product to end-users. This includes digital options for purchasing, and also the variety of retailers in your network that are using these transformative processes too.
  • Data & Analytics: Data is key with digital transformation. Operating in a digital space now gives you the data to analyze what strategies work and will resonate with your consumers.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

Creating a culture of innovation is the ultimate challenge for businesses. At Upper Deck, I believe it’s very important to encourage new ideas among employees. I always welcome outside of the box ideas and thoughts when meeting with my team. If it helps to spark ideas and inspire abstract conversations — than it’s absolutely welcomed here.

It’s easy to become a linear or logical thinker — but maintaining creativity is key when remaining innovative in your industry. We should ban the phrase “this is the way we’ve always done it,” so we’re never discouraging any new ideas.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have two quotes that are somewhat similar. When I was young, my mother always told me that I’d be judged by the people who I surrounded myself with.

Very early on in my career, I worked with a manager that said you should always surround yourself with people who are smarter than you.

These are two quotes I keep in mind often, as I always like to surround myself with problem solvers, creatives, and strategic thinkers, so I can consistently learn from them and continue to challenge myself.

How can our readers further follow your work?

Thank you so much for sharing these important insights. We wish you continued success and good health!

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.