[E271] Tales of a new CRO, with Darryl Praill (Part 1)

Jason Cutter: Hey, welcome to another special guest episode. On this episode, I have Daryl Prail. You're going to hear us talk about a lot of things. If you're a longtime listener or fan of the Sales Experience Podcast, you know that Daryl was on season one. was actually in episode 30a and some background on Daryl. So Daryl is now the chief revenue officer at Vanilla Soft, the industry's most established sales engagement platform. That's what's in his bio. And it's true. I've seen it in action. I think it's a great piece of software. There's many others in that same market, but it does really great stuff. As far as the other information about him. Accomplished award winning marketer sales world top 50 keynote speaker. I saw him speak at a conference, which is how we got connected and have continued the relationship 2020 top 10 SAS branding expert, top 19 B2B marketer to watch in 2019 social media influencer category, leading podcaster. serial entrepreneur. He's done everything from VP of sales, consulting, chief marketing officer, and now CRO. He's raised a ton of money for organizations. He's done so many things and I'm excited to have him back on the show because at the time he was a CMO, chief marketing officer, and now he's a CRO. And so under a year and a half, he's made a big transition and learned a lot and saw a lot. And if anyone knows me, part of my mission. Is to help bridge those gaps and bring together sales and marketing instead of it being a us versus them. It's everyone rowing in the same direction, which the CRO position does. So this is a great conversation. It's gonna be a four part. We go through a lot of stuff. He shares a lot of great tips. If you're an owner of an organization, a CEO or an executive leader in an organization, this is a must listen set of episodes because he's going to share with you the challenges he faced. the struggles, the plan that he put in place, and then some tips for getting to a place where you're going to put a CRO in place. And if you're a CRO listening, obviously there's some value packed in this. And then for everyone else, if you're in sales or marketing more at the frontline level, it's so important to hear what is structured in organizations when it's done properly, where there is that person at the top that's bringing everything together. So Enjoy my conversation with Daryl. Daryl, welcome back to the sales experience podcast. Darryl: That's how I'm just fantastic. Jason. Welcome back. You had me back. I'm sorry, dude. This is awesome. Jason Cutter: Yeah, and you do have the honor and distinction of being the first return guest to the sales experience podcast. Our episode, our conversation, which was super fun, was May 24th, 2019. It was episode 30A. At the time, I was trying to keep it clean numbers one through five every week. And this was a bonus episode, and obviously a bit has gone on since May of 2019. Darryl: May of 2019, the world has changed, my friend. Oh my goodness, has it changed. We have lots to talk about. What are we talking about today? What do you want to talk about? Jason Cutter: I think what's fun is a little recap for people. So you work for a company, Vanilla Soft, which makes some great technology to help with call center salespeople to manage their pipeline of leads and does a lot of things. What's fascinating is we first met last year, early in the year at Martech conference, where you gave a presentation to a conference full of marketers called the day that marketing held sales accountable, which was, you might say it's a little click baity, even in your own words. But really an important topic and then since that time to now, you're now the CRO of vanilla soft, which is the chief revenue officer, which is in my mind, a newer term that has been made up to signify that person who's now in charge of marketing and sales as a joiner of them. Darryl: It's true at the time when I gave that presentation of the chief marketing officer. And of course, that's your point, vanilla soft sales engagement platform. So we would sell our product largely to sales leaders to be used by their sales teams. All the topics and the content we speak about is often sales related. Ironically though, marketing leaders also have a vested interest in making sure that the leads they generate for sales are actually followed up on with the right speed to lead and the right persistency and the right cadence and the right channels because marketing leaders are measured by the revenue they contribute. Okay, we give you a million dollars to spend on whatever programs. How much revenue did you drive? So both of those personas, the sales leader, the marketing leader have an interest, but I was the CMO and therefore my conversation was the day marketing held sales accountable. And it was a fun conversation because many that when I would give that conversation. All the marketers in the room, I would ask them every time, how many people here are frustrated and feel like you've spent all this time and money and love creating these programs to generate these leads, the sales just botches it up and it was like overwhelming. How many were like, Oh yes, preach hallelujah brother. That is, talk to me. And I was like, I was a kindred spirit. Let me walk through and the sales reps were always interesting. The sales reps would always be. Reserved. And they'd watch the conversation, and then they would watch it, and I would just walk through it. I would show how it was never malicious. Sales was never intentionally trying to physically botch it up, as I say. And they would come to me after the conversation, they would say, I was really suspect of your topic, but I got to say, you nailed it. And one of the things I would talk about in the presentation was how Reps cherry pick. So marketing, you generate, say, 10 leads. But the reps go, Oh, lead number three. Oh, lead number seven. Oh, lead number nine. Those are really cool. I'm going to call them first. And the marketers are going aren't you going to call the rest of the leads that we made all this time and money making? And the reps would always come up to me and they would say, I'm totally guilty of cherry picking. You're right, you nailed it. And I would say, yeah, I understand why you're cherry picking it. But let me show you how we can help you fix that. So Mark seems happy. And you call all the leads, because if you call all the leads, maybe number two and number six are the ones that actually close, even though you skipped them initially. So that was the premise of the conversation. And you're right. It's easy for me to sit up in my ivory tower as a marketing leader and say, sales, you need to do this. Stop boxing it up. You're affecting my ROI. But now, your point, fast forward a year later, and now I'm the chief revenue officer, I own still all of marketing, but also all of sales. And I'm the one who has to actually be accountable for the number. Ironically, it's be careful what you say, folks, because suddenly they're gonna say, Oh, you think you can do better? Here's the keys to the kingdom, show us how it's done, buddy! Jason Cutter: And that's where I'm at. One thing I've seen is that sales people worry about only being able to win if they use manipulation, tricks, tactics, and hard closes. So they end up struggling to close deals, make their quota, or earn the kind of money that they want to make. If this sounds like your current situation, or maybe you want to make more money in sales without feeling like you're selling, then my upcoming book called Selling with Authentic Persuasion will help. In it, I'm going to take you on a journey to transform from order taker to quota breaker. If you're ready to become an authentic persuader, crush your goals, and create success in your sales career, then go to jasoncutter. com. Again, that's jasoncutter. com and pre order the book today. And I remember sitting in that audience, being a sales guy, being a consultant, and generally Before the title of CRO was a thing being that person, right? VP of sales marketing. One time I had my title was VP of sales marketing and operations, which was a little wordy for a business card, but it's basically tying everything together. So I remember sitting there and thinking you're a hundred percent right. And the way you did it was great. It wasn't okay. Everyone, pitchforks. Let's go kill sales. It was. Marketing is doing this. Sales is doing this. Everyone needs to work together. And if you put some tools in place, then sales can do what they do best, which is have conversations with the right people at the right time being served up by, shameless plug, something like Vanilla Soft. But just anything that enables sales to just work on all the leads. Darryl: Sales Loft, you can use Outreach. I compete with them in certain industries. The whole premise, though, is use the tools. They're for a reason. And that was the whole premise of the conversation, was that so many people, they'll sit, we're all guilty of this, we're all people, right? We'll all bitch and moan sometimes about how the cards we've been dealt and the other guys sucking and they, I hate them. And the reality is, it's not that they suck. You shouldn't really hate them. If anything, go out for drinks together. Or, in this modern era, go out for an e drink together. Get to know each other because the reality is you actually want the same thing. You're just approaching it from different spots. So try to find some common ground and try to support and lift each other up. And this was the case in my presentation on marketing, marketers. This is how you can help sales. And if you help sales, it's actually ironically going to help you. But yeah, no, I have it now and it's interesting, one of the things I said to my CEO, I remember him coming to me because there's always that pre conversation, right? So before it's hey, Daryl, we're going to promote you because at this point in time, it's never, I was already a CMO. So it wasn't like, maybe I didn't want the job. Maybe I didn't want to be promoted. Maybe I didn't want to have that nut for the quota. So he comes to me and he goes, Hey, I'm thinking about maybe we should hire a CRO. And I'm like, okay, yeah, cause we had a VP of sales before. And he says, if I were to do that, he goes, would you at all be interested in the job? And I'm like, Oh, okay. And so from there, the conversation went, he was great. I had time to think about it and make sure we had expectations of line and all that great stuff. And it wasn't just handed to me. I had to go and create a whole plan. I had to go present it to the right people and blah, blah, blah. There you go. But. I remember saying to him the day he announced it, it was, hey, the whole company internally, Darrell is now the CRO and I reached out to him and I said, dude, that is such a weight on my shoulder. I see these young companies where they have five or 10 people and there's some 25, 20 6-year-old person who is the CRO? And I said, you're not the CO, you're just a glorified sales rep. Maybe you've got an intern. That's about it. You're not the CRO. I'm sitting here at 52 years old. And I'm going, I now know what it means to be the CRO. I've lived it. I've got the battle scars. I've been hired. I've been fired. I've been beat up by VCs. I've watched other sales leaders fail miserably. I know exactly what I'm stepping into and it is a heavy burden. And I remember him saying to me, so then Darryl, if I can be so bold, why did you take the job? And I said, Oh, that's an easy one. I took the job for one simple reason. And he goes, what? I said, control. And he goes, help me understand. I said, the friction is gone now. The marketing Darrell says, I think we need to do this. And he turns to sales Darrell and says, if marketing Darrell does this, will you do this? And sales Darrell says, you're damn straight. I will. Boom. Let's go. Let's go do it. So that's what I liked about, and that's why I took it, was the chance to go really fast and make a difference. Jason Cutter: Alright, that's it for part one of my conversation with Daryl Prail. Make sure to go find him, easiest place, Google Prail, or you can go to darylprail.com. You can find him on LinkedIn as well. And I will see you in tomorrow's episode. That's it for another episode of the Sales Experience Podcast. Thank you so much for listening. If you find yourself on iTunes, can you leave the show a rating and a review? It helps other sales people and sales leaders find the show and please subscribe to the show and share episodes you find valuable with anyone you know in sales. Help me on my mission of changing the way sales is done. And if you're ready to work together, go to Jason cutter. com. Again, that's Jason cutter. com. To find out how I can help you or your company create scalable sales success. I will see you on the next sales experience podcast episode, and keep in mind that everything in life is sales and people remember the experience you gave them.