HomePressWelcoming Outsider CEO Deirdre Lester

Welcoming Outsider CEO Deirdre Lester

by Shannon Terry

A friend and mentor reminded me of an adage more than a decade ago, and it has remained at the forefront of our business strategy. 

“Bet on the man/woman, not the plan.”

If I’ve learned anything, building a great brand starts with hiring the right people and letting them do their job.

On Wednesday, Outsider announced that former Barstool Sports Chief Revenue Officer Deirdre Lester had been appointed the company’s CEO.

When I started searching for the company’s CEO, Deirdre was my first and only call. We had received a lot of inbound interest for the position, but there wasn’t a second choice. It was never a matter of “if” we were going to work together again; it was a matter of “when.”

Deirdre echoed those sentiments when she tweeted out the announcement:

I first met Deirdre in 2004 when she worked for ESPN digital. She made an immediate impression, and I recruited her to come with me to Rivals.com in 2005 to build our direct advertising sales initiative. She crushed it. 

After a short stint at Yahoo! following the Rivals’ acquisition, she moved to a senior position with Major League Advanced Media (BAM). To this day, I still consider BAM being one of the most successful digital media companies of all time. She crushed it. 

Over the past decade, we stayed in contact. When Deirdre called me in January 2018 about an opportunity to work with the polarizing and fast-growing media brand Barstool Sports, I wasn’t going to let her say no. I remember those calls vividly. 

She crushed it — and that is an understatement. As CRO, she helped the company grow revenue exponentially over the next four years. Simply put, she was good for Barstool, and Barstool was good for her. 

Deirdre has executed at the highest levels for some of the best and most notable brands in media. Her portfolio of experience places her in rarified air. She had unlimited opportunities to lead any number of companies, but she chose us. Choosing her was easy. 

As Outsider attempts to build a world-class media and lifestyle company, it’s going to take a lot of talented people to reach our goals. Most importantly, it’s going to take the right people that buy into our culture. 

With Deirdre, I am often reminded of the Ralph Waldo Emerson quote that was fervently preached by my former college basketball coach, Don Meyer. 

There is no limit to what can be accomplished if it doesn’t matter who gets the credit.’

Not only does Deirdre have a wealth of relationships and experience in our category, but she is also the consummate team player. As she transitions into the vital leadership role of Outsider, we can all rest knowing she will demand a culture of not only excellence and accountability but a company built on the foundation of TEAM first. 

Our opportunity with Outsider demanded we find a “unicorn” to lead the vision, and I think we may just have found one.