• April 18, 2026

Sports Illustrated CEO Reconfigures the Website Monetization Strategy

Ross Levinsohn In 2016, Ross Levinsohn started working as Sports Illustrated CEO, and his introduction to this role came at the perfect time. With its 70-year history, the publication had an established revenue stream with a great monetization strategy. Unfortunately, that monetization strategy had been stressed in recent years. Like other notable media brands, Sports Illustrated’s website had seen increased traffic since the turn of the century. At the same time and as a direct result of the internet’s popularity, the brand saw its print subscriptions decreasing. The net effect of these transitions was lower revenue. Tweaking the brand’s monetization efforts was an immediate and major goal of the Sports Illustrated CEO.

Levinsohn is a key executive leader who has served his chosen industry across four decades. Prior to joining the sports publication brand, Levinsohn was the top leader at Maven Media. Through this influential role for the digital media service provider, he was able to fine-tune monetization strategies for some of the provider’s 300 brands. One of several notable examples of his innovative mind at work was at The Street with Jim Cramer. This finance brand’s core content had been focused exclusively on Wall Street stories. However, cryptocurrencies were growing in prevalence in the financial sector. Levinsohn saw this as an incredible opportunity to elevate monetization for the brand. Specifically, a new line of crypto-based content was innovated and is now available through a special paywall.

For Sports Illustrated, Levinsohn realized that the solution involved raising more revenue from established content rather than producing even more content. The Sports Illustrated CEO decided to offer select stories as early-release content. These top stories now produce more income through Levinsohn’s premium paywall.

Levinsohn’s activities for these companies and others have served as inspiration for other brands that were struggling with monetization. He also has made other significant improvements to the industry overall through work at major enterprises like Yahoo!, Whisper Advisors, Fox Sports and others.