Ryan Skeggs is Digital and Data Managing Director at sports, music and entertainment agency Wasserman. Ryan is an award-winning digital specialist with a media career spanning fifteen years, with past roles at companies including Mail Online, Bauer Media and Greenroom Digital.
Who is your digital hero?
Chloe Hawking, currently CEO UK & President EMEA at Kinesso.
What has she done to earn hero status in your eyes?
Chloe is a true pioneer in the digital space. She is one of the few who consistently understands emerging digital trends and can craft a clear narrative around their importance.
She not only identifies the trends but also quickly realises how to capitalise on them, while educating others in the organizations and brands she represents. What stands out most to me is that she does all of this without any need for fanfare, always moving forward at an impressive pace.
How has her heroism helped drive digital innovation?
First and foremost—leadership. Chloe approaches her role with the mentality of a startup leader, leading from the front and rolling up her sleeves, even though she oversees significant operations.
Secondly—education.
Digital is an ever-evolving field, and one of the biggest challenges is articulating the value of digital innovations to both internal and external stakeholders. Throughout her career, Chloe has designed scalable digital solutions that have transformed the way businesses think. Whether it’s creating new, innovative commercial models or ensuring brands stay competitive in the fast-moving digital world, Chloe has consistently been at the forefront.
Lastly, and perhaps most importantly, Chloe has broken through the glass ceiling, serving as a trailblazer for change. It’s rare to see women in the top C-Suite positions especially in the digital field. Chloe’s success is a beacon of hope, showing others that they too can reach for the stars and achieve their goals. Without even realizing it, Chloe has become a role model for many in the industry.
What are the biggest challenges in digital that we need another hero to solve?
One of the biggest challenges we face is developing robust AI governance.
My concern is that, in its infancy, generative AI in media may follow a similar trajectory to the rise of programmatic media, where we saw bad actors exploiting the system for profit. We need to learn from past mistakes and focus on educating the market to deliver on the exciting potential that AI brings to the next phase of digital evolution.
What is your most heroic personal achievement so far in digital?
After working in finance for 12 years, I decided to make a bold step into digital media—a move I’m particularly proud of. Sixteen years ago, I took a chance on myself, embracing the process of learning, failing, and adapting to new skills. I’m glad I made the jump, especially since it led me to work in sports, which has always been my passion.
From a project perspective, my proudest achievement was driving a nationwide behavioral change program for one of our partners. It was incredibly rewarding to use our expertise not just to drive revenue but to inspire and deliver a healthier nation. This program is now in its third year and continues to deliver outstanding results.
