Deirdre Lester tapped to lead as CEO

by Outsider

NASHVILLE, TN. March 9, 2022 –, a rapidly growing digital media and lifestyle company, announced today that former Barstool Sports Chief Revenue Officer Deirdre Lester has been appointed new CEO of the company. 

“Deirdre completely understands the brand mission and opportunity with Outsider,” said Outsider Co-Founder and former NFL Quarterback Jay Cutler. “She is extremely talented, has years of experience and a known track record in the industry, but what impresses me most is her team-first attitude and leadership skills.” 

Lester will be tasked with expanding the media and lifestyle company’s mission of celebrating American culture through real stories and authentic goods. 

“Barstool was an amazing experience for me, having an opportunity to be a part of staggering growth and work along so many dedicated, passionate, and talented executives and talent,” said Lester. “I will forever look back on my experience as one of my proudest professional moments.” 

“I’ve been keeping up with Outsider from the sidelines and when the opportunity to lead the company as CEO was presented, It was without question the entrepreneurial leadership role I’ve been building towards for years. The Outsider mission to build a community that celebrates American entertainment and culture has endless potential and I’m thrilled to be at the helm of building this company to be an industry force.”

Outsider’s media division is building a portfolio of podcasts and shows, featuring production from Co-Founder Jay Cutler and “The Marty Smith Podcast”.  In addition to the media division, Outsider recently launched its lifestyle store, with a small offering of custom-built hats. The company has plans to release a full line of products serving the Outsider lifestyle in the near future.

“When the search for our CEO began, Deirdre was our first call.  She has executed at the highest levels at best in class digital brands her entire career,” said Outsider Co-Founder Shannon B. Terry. “Deirdre’s portfolio of experience puts her in rarified air.  She had unlimited opportunities to lead an organization, and her choosing Outsider is a testament to our enormous opportunity.” 

About Deirdre Lester

Deirdre Lester has over 20 years experience in the digital media industry, with a focus predominantly on sports & entertainment brands.  She began her career in media at CNET Networks in the late nineties and went on to work at ESPN as her foray into the sports business.  Deirdre has held executive-level positions at, MLB Advanced Media, Whistle Sports, and most recently was the Chief Revenue Officer at Barstool Sports where she led Advertising & Sponsorship and Brand Licensing.  She has been named a Top 25 Women in Sports by Forbes (2016) and Top Digital Executive by Mediapost. 


Outsider is a media and lifestyle company that celebrates American culture through the entertainment, sports, and news we cover and the authentic goods we create.

Outsider reaches more than 22 million users and more than 7 million social followers. Along with former NFL quarterback Jay Cutler, Outsider was created by the founders of, (acquired by Yahoo! In 2007), 247Sports (acquired by CBS Sports in 2015), and Pop Culture Media (acquired by CBS Interactive 2017).