Darryl Praill’s Number One Secret to Marketing ROI

This week on Digital Conversations, we feature Darryl Praill CRO at VanillaSoft. He goes over the challenges of aligning marketing and sales as well as why you should incorporate video into your marketing ROI strategy. He focuses on the extraordinary returns that come from optimizing SEO and proven steps to improving your SEO efforts.

Guest: Darryl Praill is the Chief Revenue Officer at Vanilla Soft. By education, he is a computer programmer. He has worn many hats including CMO, SVP of Sales and Marketing and VP of marketing and strategy.  He is a big fan of marketing and has been a CMO multiple times. He’s also raised over 100 million dollars of VC funding and gone public twice. Follow him on LinkedIn!


Billy: Alright, everyone, welcome to digital conversations. I am your host, Billy Bateman. And today I have the pleasure of being joined by Darrell Praill. Darryl, how you doing?

Derryl: Man. I’m doing well, Billy, how about you, my friend?

Billy: I’m doing good. I’m excited to have you on today. We’re gonna talk about a few really interesting things. But before we get into it, for those of you that don’t know you, I don’t know if there’s many people that haven’t at least heard of you. Tell us just a little bit about yourself and about Vanilla Soft.

Derryl: Alright, so if you don’t know about me, you should count your blessings. And I’m sorry, that has to change today. So I’m the chief Revenue Officer here at Vanilla Soft. Vanilla Soft is a sales engagement platform. So we target sales reps AEs and SDRs, who are looking to do multi channel email, phone, social SMS outreach, using sequences or cadences or playbooks pick your term. That you can actually just engage more people and generate more activity for yourself. That’s what we do.

That’s who I am. By education. I’m a computer programmer, I have sold. I’ve been upwards of being a VP of sales. I have big fan of marketing, been a CMO multiple times. I’ve been hired, fired, acquired, been the acquirer gone public twice and raised over 100 million dollars of VC funding. So I have earned every single one of my white hairs I have.

Billy: It sounds like you have man. Okay, let’s get into it though, today. You’ve been at vanilla soft, a little over three years, and you started out as the CMO. And now you are the CRO. How did that happen?

Derryl: How did that happen? How I mean, like everything else, the company had aggressive targets. And whilst we were doing very well, with our revenue achievement, we weren’t hitting the aggressive targets that we had in place. So does that mean, it’s a sales issue? Is that mean that our targets were perhaps ludicrous? Maybe a little bit of both. This is how it all this is literally how it all began.

Part of my compensation is tied to corporate revenue attainment. So as a CMO, I was bringing in my team and I were bringing in massive amounts of marketing ROI qualified leads, exactly as sales wanted, yet we weren’t hitting those numbers. And as you might imagine, that affected my pocketbook, because I didn’t get my annual bonus.

So it all began one time, but a year and a half in my stint when I went to the CEOs office, and I said, I’m frustrated. He said, Why? I said, because I’m doing my part of the job. And I’m getting shortchanged here. And that led to a fair point, it’s been on my mind, what do we need to do. So we spent the next kind of year, year and a half, trying to do a lot of stuff, to get sales to hit the targets. That brought in outside experts. And every we spent a boatload of money on technologies, advisors, and everything else.

Didn’t make it, they had to make a decision. And as you might imagine, their decision was pretty straightforward. And this is what I’m told after the fact, which was we either replace the head of sales for other head of sales, or we hire zero, but Darryll is already CMO. So that probably wouldn’t go over so well. Or we give the job to Praill. What was interesting was, I don’t think give the job to Praill was their first choice. What they started to think about was the cultural fits, and the time opportunity costs. And what they realized right away was that I already knew the space.

The people knew me, I knew them, I knew how to sell I had sold. And if they brought in somebody who wasn’t strong enough, they told me that I would probably chew them up and spit them out. So to avoid that problem, all together, they decided to give me the job, and then backfill my role. But what I really respected about the CEO when he did this, because I get asked the question a lot are you really CRO? Are you just really a VP of Sales and Marketing, which is a legit question. And if you don’t know the difference, we can have a conversation.

He said to me, Darryl, you know, if we give you this job, I’m offering to you on one condition, I said, What’s that? And he said, that you truly backfill yourself. So you can be the CRO, I do not need a VP of sales and marketing. That’s what I need it, I’m gonna let you in your role and just got a VP of sales. So that was the the requirement that was given to me, and that’s what I’ve been doing ever since. And full disclosure. I’m learning on the job a little bit, which they knew I would, but there’s not a lot of CROs who are former marketers. So there you go.

Billy: So as someone, you’ve been a VP of Sales now you’re a CRO. So like, for those of us that maybe aren’t as familiar, what’s really the difference? How would you break down that difference?

Derryl: So the biggest difference comes down to, let me put it this way. I like to use an analogy. There was once upon a time I was in high school way back when I used to play chess, professionally, and I was ranked and everything. I even have chess trophies, I want you to know that. Why does that matter? It matters because that’s how I view the world. I view the world through a chessboard, and in chessboard, you got all these pieces. And they move in different ways. And they they’re used in different situations, a queen can do something, a King a do something and rook can do something else. But they’re all available to you.

When you’re a VP of sales, you only know half the board. So the other half the pieces you never get to touch when you’re VP of marketing or CMO, you know the other half of the board. Yep. If your VP of Sales and Marketing, that means you still only know half the board, but they think you’re smart enough to learn the other half. We hope, or we can’t afford to make you a CRO with the salary or the incentives that come with it. So that’s the VP sales. And ultimately, if you have two individuals, a VP of sales and a VP of Marketing, when a decision needs to be made, it gets made, who’s the arbiter there’s a tie marketing ROI wants this sales wants that? Well, incomes the CEO, often who breaks the tie.

But the problem is the CEO often is like a VP of sales and marketing. They only know one skill, they might know sales, might know marketing ROI, they might know neither that may be an engineer, an innovator. So are they the right person, what a CRO is somebody who’s done it all and knows all the pieces on the board. I am a head of marketing ROI for years, I am a head of sales for years, I have carried a bag, I have been a sales engineer, I have done customer success, I have been customer support. I’ve done all of that.

So I know what I have available to me. Plus, I’ve got the budget of marketing, which means I can now not just move pieces around, I can move money around if I want to take some money away from marketing, and instead hire an additional account executive. I can do that. Because management only cares about my top line spend. Where as well as a VP of sales or a VP of Marketing. There’s no way either one of those positions are giveing up the money for the team. So it’s really the ability to understand when do I use marketing when do I use sales and how to make them work together. And that is honestly a really rare skill.

Billy: Yeah, so how do you like it, man?

Derryl: Jury’s out. I miss being the CMO because I love doing my hands on I backfield myself. And I get to watch my director of marketing have all the fun that I used to have. So I i pine for that stuff, I may have some control issues. And on the sales side the reason I asked you ultimately said I’m gonna go all in on marketing, and I kind of left sales was because twofold. One, I really hated having that quota over my head all the time.

And two, I love you sales folks. But sales reps are the most insecure people going. And I said that with love and attention and respect. And there is fear for lots of reasons, right? Because they’ve been screwed around so many times. So when the head of sales or marketing whatever says this, but secretly message each other all the time, they say, do they really mean that? What do you think he really means and it’s conspiracy theory Central, right. And they’re, they’re texting each other offline. So it’s not to be on the public record in a second number ready. When I said this, I just meant this. Stop trying to read it. Look into my words. So they’re getting them to trust you is hard. Having that quota sucks.

But what I love is our teams have never been more aligned. We are unified, we work together, there is no sales v marketing. This is the revenue team. In fact, my weekly call I have is called the revenue team. We got product marketing in there. And we got sales in there. We had corporate marketing ROI in there. That’s the revenue team. We drive this engine and we’re united and that’s cool.

Billy: Awesome, man. Oh, you’re right salespeople. Man, they are so paranoid, and they have every right to be. It’s I mean, who gets cut first when numbers don’t get hit? Sales marketing. But often sales guys aren’t hitting quota you’re gone.

Derryl: And it’s the nature of the beast. I had a two hour call with a rep the other day. True story. I don’t think he’ll mind me saying this. Where it’s like Dude, I just feel like we’re not in the same wavelength What’s going on? And when you drill down to it, we finally started peeling back the layers of the onion getting real each other. It was he didn’t trust me. And the reason it didn’t trust me was because I let another rep go soon after taken over. And it was his opinion that other rep was rocking it. Why would I let them go? Therefore I don’t believe anything you say Praill.

And my response to him was, I’m sorry. Did you ever talk to me about this other rep? No. Have you heard my side of this other rep? No. So you think he was kicking ass? Yeah. Because he told you that. Well, yeah. Okay, dude, you got half the story. Let’s let’s talk about the rep. Oh, I didn’t know that. I didn’t know that. Oh, I didn’t know that. Okay, full stop.

Secondarily, I hired some more people in different roles. I hired some sales solution engineers. are you liking them? Oh, my gosh, best hires ever. Okay, that fund that money didn’t magically appear. So when we let those people go, now they had funds to go hire these people over here. So they were underperforming. I move some money around. And now you’re a happy camper. Oh, I didn’t know that. You’re right. You didn’t know that. Why? Because you didn’t talk to me.

Stop second guessing. You’ve got a problem come to me. I didn’t have that problem in marketing. I don’t know if they’re wired differently. But in sales, it took me a while to go. I remember this now.

Billy: I love salespeople. But man, you have to over communicate with them.

Derryl: You have to over communicate, bingo.

Billy: So okay, while I’ve have got you, you have been around the block CMOS, CRO, VP of sales, big companies, small company. And one of the things I really wanted to drill in with you is, okay, you’ve done a lot of different things. If I’m a small company, and let’s say I don’t have sales, I don’t have marketing. It’s all together. Like, we all work together. We’re all aligned, full circle sales rep, one revenue team. What is the one thing you would do that you’ve seen have the most ROI for you in the past?

Derryl: Oh, I love this question. I got asked this question recently. And actaully at the time it made me stop and think about, what is it? And I might have given a different answer, a year, year and a half ago than now but they are related.

So like most people, I don’t have 100 million dollars in VC funding. My two biggest competitors have raised almost $300 million each, I have raised less than 1% of either one of them. And I’m competing against those people. So how do I? How does the company compete against that? So it’s exactly what you say we’re a lean, mean fighting machine. We mean, well, but we don’t have the same resources, whether it be people or a budget.

Further, we run our business to be profitable, whereas many VC funded companies are designed to burn money for 18 months or more where they get market share. We’re not. So what do you do? And the answer is Billy, sounds stupid kind of be lame. SEO, search engine optimization was the biggest ROI for it was. And it was for many reasons.

When you commit to it, it’s actually relatively affordable to do. You do need the skills initially, we did outsource that I paid thousands of dollars every month to some experts then actually we hired in house. That’s the first part. But to make SEO work, you do have to commit to a certain volume of content, because that’s what you’re optimizing, whether it be ebooks, or your videos, or your websites, your landing pages or what have you. But you want content anyway, because that’s what drives inbound. So the assumption is, you’re already going to do content, a blog post on its own, it’s not going to drive much for you, but an optimized blog posts could drive a boatload of activity for you.

So why Seo? Because you say, we all do that already. Because if you do it right, that people who are finding you have high intent. In other words, they went looking for you. If your keywords match up with their searches, then you’re going to be a match and a fit for them and they’re coming to you not to say why you bother me to come to you because they’ve got a problem. And they’re actively seeking a solution. They stumbled across you. So therefore they’re already in the market seeking solutions.

Now maybe it’s you maybe it’s not me but can afford you maybe they can’t but out of the gate. They came to you so you can sit in by other lists you wants you can you can spam an email and cold call. Till you’re blue in the face. And that’s a numbers game and it will work. Yeah, but there’s nothing like an ROI on SEO. And I’ll tell you this, when I got here, our number one lead source was pay per click, very expensive, and the cost per lead through the roof.

We invested in SEO within six months. We just saw a complete shift SEO became our number one lead source and it’s just gotten bigger and bigger and bigger. And I’m still dropping a boatload on Pay Per Click every month, and the cost per lead. And the average cost customer acquisition is so cheap, it’s scary. As well as the shorter sales cycles. So if you’re going to invest in one area, your lean mean team, make some good content and SEO optimize everything.

Billy: Okay, okay. I love it. So for those that are like, Hey, I can’t outsource it all I’ve got but I’ve got some team members that that are smart, and they can learn. What tools would you suggest they look into for SEO optimization.

Derryl: Okay, so there’s two, the two different, slightly different price points, but they’re both quite good. So for years, we use SEM rush. And it’s a great tool.

We now, for a variety of reasons, we’ve switched over to h refs. So H refs. And but both tools are really solid, it’s kind of a personal preference of what you want. They’re both relatively affordable, so they have scaling plans, you can get into h refs was great for us.

What’s great is those both those tools can also help you identify the keywords that you should be building your content around. So if you’re just making content without a plan, then your SEO efforts will stumble. But if you’re really intentional about your SEO and use it to drive your content, then it has a dramatic difference to provide a bigger impact.

Billy: Awesome. Okay, man. Man, any other any other tips on SEO while we’re on that, because it’s interesting. We have a blog, we write blog posts, we do our best to stay on topic. It’s provided return for us. But we probably actually put more money into buying lists, cold calling, emailing people than our than we do into our SEO.

Derryl: And only that is legit, you should do all of that. As far as tips, though, what you can do is in your example, you’ve got a blog. Go back to your last year, year and a half, two years and look at your top, say 2030 performing posts, and then go update them simple little thing, go update the the h1 and the h2. Your headings and whatnot, go re optimize the keywords, and they were already well performing before but now they’re gonna pay you even bigger dividends. That’s the first thing you need to know.

There’s a number of formulas out there’s a lot of great people I follow. Gaetano Dinardi already love him he’s with next to but he’s an SEO, Rockstar, follow him on LinkedIn. But there’s a lot of really good people out there do that. The other thing I would say on SEO is this is gonna sound funny. Look for excuses to optimize something.

I’ll give an example. When we do our podcasts or we do our webinars, we transcribe everything and we use rev.com. But you can you know, source it out for dirt cheap. Then we actually put that on the page as part of the show notes, everything else. All optimize h1, h2, everything else that drives a lot traffic. And we do our videos, we caption everything using the SRT file so Google can physically crawl the SRT files.

And actually again, we’re making sure that we’re getting keywords in those captions. We’re being intentional, post a couple of little examples of what you can do to actually get a big ROI on that. But the best part is look what your competition is optimizing for use that as a starting point. Clearly, you may not be able to out spend them but there’s the you can certainly compete with them.

Billy: Yep. Awesome, man. I love it. Now our time’s running short. So before I let you go, I want to ask you, is there anything that you’re like And if this guy was smart, he would have asked me this question that I should have asked you.

Derryl: Ask me why I liked videos so much.

Billy: So why do you like video?

Derryl: You know, no one’s ever asked me that. Billy, you are amazing. You’re a rock star. I like video, because it allows my message and my spokespeople to stand out from the crowd. Everybody’s got a blog. Everybody’s got ebooks and white papers and emails. So why are you any different? Why do you stand out from the crowd?

When I do video, I get to move my arms around a lot. So as you’re scrolling through your feed , you’re watching this in real time, my hand waving catches your eye. It allows me to show my personality. It allows me to be in your face and make an impression whether you listen to what I say or not. Video is an amazing way to emotionally connect with people that the printed word or an email just can never convey. video should be a key ingredient to your mix. If you’re not committed to spend a little bit of money. It doesn’t have to cost a lot. I began using my phone. All right, you can start cheap, a phone and a little, small tripod.

But you can start cheap. And it makes a huge. For me look at you right now you’re sitting there, you’re in a wonderful little studio get nice color coordination. In fact, Billy’s sweater matches his backdrop.

Billy: I didn’t realize this when I came in today that my I was wearing the chat funnels t shirt, the chat.

Derryl: He’s got branding going on. It’s all psychological baby. So who doesn’t want more, Billy in their life when they see that? That’s awesome.

Billy: Awesome, Darrell, dude, we could go all day. But I appreciate you carving out a few minutes to chat with us and with the audience. If people want to get a hold of you and continue the conversation, what’s the best way for them to reach out.

Derryl: LinkedIn, I’m there all the time. But if you really want to find me, there’s lots of ways Twitter my own personal website, just go to Google with the word Praill. And you will find 99.9% of them are all me they all roads lead back to Darryl baby.

Billy: Okay, I love it. We’ll chat later. And thank you again. Darrell. Billy, thank you so much. Have a great day.