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People Profile: Ryan Olli, Director of Licensing & Head of Athlete Relations at Winners Alliance image

People Profile: Ryan Olli, Director of Licensing & Head of Athlete Relations at Winners Alliance

The global licensing community is powered by an incredible group of professionals whose diverse backgrounds and creative energy drive innovation and excellence. Each week we profile one of these professionals in this ongoing series.

How did you get into licensing (or how did licensing find you)?
I had the opportunity to intern with the NFLPA in the player services department, where I gained valuable exposure to various teams and functions, including licensing. I was truly fortunate to be surrounded by such a sincere and talented group of people. I became inspired by the innovative work they were doing. So, when my internship concluded, I was thrilled to return a few months later as a full-time Licensing Coordinator.

What’s a “typical” day in your current position?
It knows it’s cliché, but there’s really no ‘typical’ day in my role. The overarching mission is to create new revenue opportunities for global athletes, which can involve a range of activities like maintaining strong relationships with athletes and agents, managing and maximizing opportunities for existing partnerships, and securing new partners.

What’s your biggest personal or professional accomplishment?
Being a husband and father is by far my greatest source of pride—they’re my ‘why’ behind everything I do. Professionally, being named to Front Office Sports’ Rising 25 was an honor. I’ve got a lot of love and respect for what they’re all about and I’m excited to see their Rising 25 initiative grow. Lately, I’m especially proud of building a group licensing program in tennis from the ground up. Tackling the challenges of creating something completely new definitely makes the end result that much more rewarding.

What are the most significant trends or changes that you’ve seen in the business in recent years?
The demand and need for transparency and education about the business of licensing with athletes. The trend of self-branding and NIL has heightened the attention and interest of athletes and, as a result, this generation of athletes will be the most educated and proactive about understanding the business of licensing. As licensing professionals and athlete advocates it is our responsibility to offer personalized attention, dedicated support, and necessary resources to empower athletes in navigating the licensing landscape.

What keeps you up at night? What’s your biggest challenge these days?
Well, aside from my daughter, what really keeps me up at night is asking myself, ‘Am I speaking the right language?’ As we venture into the uncharted waters of group licensing in global sports, I’m constantly thinking about how I can improve communication, both internally and externally, to make sure everyone is aligned, confident, and well-supported.

In your opinion, what is the top skill every licensing executive should have in order to succeed?
In my opinion, situational awareness is crucial. Licensing thrives on partnership and collaboration, making it essential to understand the environment and the people within it. By fostering situational awareness, you can make proactive decisions, adapt to change, and enhance communication—all of which provide your team and organization with a competitive advantage.

What’s the best piece of advice you’ve ever received, or what’s your favorite quote?
“People will forget what you said, people will forget what you did, but people will never forget how you made them feel” – Maya Angelou.

A manager of mine once shared this quote, and it has stuck with me ever since—shoutout Josh Gregory. For me, it helps put everything into perspective. Projects come and go, jobs come and go, but the impact you make on the people around you is what endures—shaping the legacy you leave behind.

What is your favorite licensing deal of all time? (It doesn’t have to be one that was signed by you.)
I’m really impressed by what Unrivaled and the WNBPA have done, empowering players to leverage and monetize their intellectual property within both leagues. It’s a true demonstration of putting players first. I love everything about what Unrivaled is doing, and to accomplish what they did in just their first year of a new league… I’m eager to see how they will continue to evolve.

If you weren’t in licensing, what would you be doing now?
Supporting athletes through a different channel. Athletes are drivers of culture, both within and beyond their sport. The positive impact they can have on society, using their platform to unite people from all backgrounds, is boundless. I’m driven by the opportunity to help people unlock their full potential.

The last licensed product I bought was…
I’m a big fan of the Kith x New York Knicks collaboration.  Just picked up a tee and hat, and I’m excited for a deep playoff run!

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