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Deirdre Lester | An Unstoppable Woman in Media

In the latest episode of Alexander Group’s Media Sales: CONFIDENTIAL podcast, host Matt Bartels, principal and Media practice leader of Alexander Group, chats with Deirdre Lester, chief revenue officer of Barstool Sports, as she shares four key pieces of advice for becoming one of the most powerful women in sports. Listen to the entire podcast episode to hear all that Deirdre had to share about her personal media sales journey, balancing work and life and how important it is to forge your own path.

  1. Put Yourself Out There
  2. Multiple Irons in the Fire
  3. No Publicity Is Bad Publicity
  4. A Powerful Leader in Media

Put Yourself Out There

Deirdre had quite the unique start to her journey in sales. While she kick-started her career in the late ‘90s during the technology boom, she found herself naturally drawn towards the media industry. Starting out as the assistant to the VP of Sales, Deirdre found herself working her way up the sales ladder even though she was not technically a part of the sales team. Her willingness to go out on a limb mixed with her competitiveness propelled her into a sales career and allowed her to grow quickly within her industry.

Today, Deirdre is a trusted leader in media sales with over 20 years of experience and is someone considered by many to be a digital pioneer. Don’t be afraid to put yourself out there.

Multiple Irons in the Fire

Diversifying your organization’s revenue streams is critical in today’s economy, especially given the uncertainty of the last 18 months. In the episode, Deirdre explains to Matt that one of her favorite things about Barstool Sports is the lack of dependency on any one channel. For example, they have a thriving e-commerce business that can balance out the ad business if there’s an off quarter and podcasts that can balance out video revenue. Having multiple irons in the fire helps Barstool Sports continue to flourish in 2020.

“I have predominantly been in the digital media, advertising and sponsorship space, and I love that… but when you’re at a company where that is your only form of revenue and there is any kind of market downturn, that can be a real problem.”

No Publicity Is Bad Publicity

It’s also important to have perspective – don’t focus on the negative media coverage. As a revenue leader, if you know your company is doing well, that’s all that matters. Deirdre shared with Matt that no matter how many fundraisers you hold or charities you support, mistakes are inevitable. A leader needs to be willing to brush it off and move past that.

“When you have people for over a decade who’ve been trying to make people laugh and be funny… Not every joke is going to land. And sometimes things get said that, later on when they come to light, don’t look as great or don’t look great at all…I don’t worry about that too much.”

A Powerful Leader in Media

The one thing that might not surprise you about Deirdre is that she never says no to a challenge. If you’re easily defeated by rejection, you won’t survive in sales. You have to be open and accepting of failure. The impact of the losses you will experience in sales can lower your motivation and even break you if you let it.

“Don’t be afraid to take risks… Forge your own path, maybe leave a trail if you can. As a leader, you don’t need followers. You need to want to bring up other people and have a high degree of consideration for those who work with you, around you and for you on how you can help them advance.”

The Media Sales: CONFIDENTIAL podcast features one-on-one conversations with media sales executives, highlighting personal journeys, career paths and insights on leadership, team building and career development. Take away expert advice for navigating the media industry and best practices for career advancement.

Sign up for the exclusive podcast newsletter to receive advanced notice of upcoming featured guests, release dates, show notes and audiograms, or contact the Media Sales: CONFIDENTIAL team if you’d like to be a guest on the show.

Listen in to get the inside scoop on all things media sales!

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