Charles Gillespie

Charles is an online gambling industry expert and co-founder of Gambling.com Group, with 20 years' experience across iGaming, sports betting, technology and digital marketing.

Since starting the business in 2006, he has helped transform Gambling.com Group from an online sports betting start-up into a Nasdaq-listed global company providing marketing and sports data services to the gambling industry.

His experience spans Europe, Asia and the U.S., giving him first-hand insight into the regulation, technology and commercial trends that have shaped online gambling over the past two decades.

Areas of Expertise

• Online Gambling
• Sports Betting & iGaming
• U.S. & European Gambling Markets
• Gambling Technology & Regulation
• Performance Marketing & Industry Strategy

Professional Experience

Charles co-founded Gambling.com Group with Kevin McCrystle in 2006 while studying at the University of North Carolina at Chapel Hill, where he earned a BA in Political Science and Entrepreneurship. The pair initially moved to Shanghai to launch a sports betting information business focused on the Asian market before changing direction and expanding into other international markets.

A major milestone came in 2011 when the company acquired the Gambling.com domain for $2.5 million. Charles subsequently led the Group's expansion across online casino and sports betting, including its push into the rapidly developing U.S. regulated gambling market.

In 2021, Charles led Gambling.com Group through its listing on the Nasdaq Global Market, making it the first publicly traded online gambling affiliate in the U.S. He has also overseen a series of acquisitions and investments in technology that have expanded the Group beyond its original performance marketing business.

Charles served as CEO for 20 years before becoming Executive Chairman in 2026, where his role includes supporting strategic M&A opportunities and helping ensure the Group remains at the forefront of developments in AI and technology.

His contribution to the industry was recognised in 2019 when he was named SBC Affiliate Industry Leader of the Year.

What Charles Does at Gambling.com

As co-founder and Executive Chairman of Gambling.com Group, Charles brings an entrepreneurial, commercial and technical perspective to his analysis of the global gambling industry.

His contributions draw on two decades spent navigating the evolution of online casino, sports betting, regulation, technology and performance marketing across established and emerging markets.

Charles is also an established industry commentator, having appeared in business and gambling media including BBC World News, ESPN, Forbes and leading gaming industry publications.

Every contribution follows Gambling.com's Editorial Policy and draws on his first-hand experience building and leading a global business within the online gambling industry.