High Risk, High Reward with our CRO, Deirdre

Today on Token CEO, we've got the woman in charge of Barstool's revenue, our CRO, Deirdre Lester. She & Erika cover everything from what Barstool's partnerships used to look like compared to now, growing a sales strategy from nothing, what it's like to have Dave rip your entire department a new one, and how to make it in sales. 

One of the main things Deirdre hit on in today's episode is how to make it in sales. Erika asks: "What do you think made you a great seller? And what makes great sellers now?"

Here's what she said:

Great question. I think if I'm thinking about myself over the years coming up in sales, I started as the assistant to the VP of Sales, and then just kind of worked my way through the ranks and sales. In fact, I was not part of the actual sales team. And they were doing a pitch contest because it was all former print people that were into pitch contests. And I raised my hand as the little assistant and said, "could I ever participate in the contest?" So I think, you know, a willingness to put myself out there, not afraid to go out on a limb and then also competitiveness. I love competitive environments. I grew up in sports. I grew up with two brothers. I was always competitive with them. I think if you're not competitive, you won't survive in sports because it is literally a horse race. 

Another thing is that every day you win and lose. If you get defeated by rejection, you're not going to succeed in sales. Everybody thinks they can be a salesperson until they have to repeatedly do it over and over with the wins, the highs of the wins, and the losses. The impact of those losses and how that impacts you emotionally and takes away your motivation can make or break you as a sales person. And that has been consistent everywhere I've gone. I've managed teams at a lot of different companies, all different types of personalities. And some people just very quickly realize that this isn't for me and move on. But other people just can't. Once they're on the racetrack, they can't get off of it. I still love that, and I love participating and being really close. I like to be out in the field talking to customers, being part of the deal, making even on some of the smaller partnerships, because I get really excited about the newer partners coming in and our ability to make big partners over time. But it's not it's not for everybody. 

At the same time, you always hear the saying, like "we're all salespeople in our lives, we're selling ourselves." But there's something different about a sales job where you have an actual target on your back and you're trying to hit a number. And there's all these opposing forces and pressure. We have a lot of that going on here (at Barstool). And even more now as we've gotten bigger than ever. You think about what we're doing. We have a very aggressive growth goal as an overall company, and our advertising revenue is such a big part of that. First each seller, and then that trickles down. Each sales team has a goal and each individual has their own goal they have to achieve. And they're getting bigger every year by a lot. So their focus is to hit their goal. 

And yet we have a lot of people to keep happy. Both you (Erika) obviously and Dave Portnoy, but also all the different content personalities. Everybody wants to monetize their content, because they feel that if their content is monetized, then they're having success here. For everybody that you're making happy one day, you're sort of feeling like you're letting somebody else down. And it's a constant balance of that. Sales people tend to gravitate towards the things that one drive the most revenue, so probably have the most audience. And then they also tend to gravitate towards the things that have consistently worked for them and are going to cause the least amount of disruption with their client relationships. So they're going to be effective at driving sales or effective advertising.

The rest of the episode covers Barstool's specifics on ad sales & a look inside how we generate revenue. For the rest of the episode, watching it on Youtube, and everything Token, click HERE.