On this week’s episode of Conversational Selling, we sit down with special guest Darryl Praill. Darryl is the Chief Revenue Officer at VanillaSoft, the industry’s most established sales engagement platform, as well as an award-winning marketer, a Sales World Top 50 Keynote Speaker, a Top 10 SaaS Branding Expert, radio broadcaster, podcaster, and social media influencer. He has also raised over $100 million in venture capital.

“I’ve had the success I’ve had in my career by being incredibly, uncomfortably, awkwardly vulnerable and transparent, which is saying, well, Darryl, you’ve won these awards, you’ve raised a lot of money, and that’s a lot of power brokers and a lot of rooms— How can you do that by being so vulnerable and transparent? And the reason is that people look at you and say, wow, you’re that vulnerable and transparent and don’t mind sharing it, you must be really confident, or you’re really relatable,” says Darryl.

We chat about the key differences between a sales engagement platform and a CRM, as well as:

  • Pivoting to increase your sales pipeline
  • Never being above cold-calling
  • How a pipeline solves everything
  • Developing a personal brand
  • And more

Listen now…

Mentioned in this episode:



Nancy Calabrese: Hi everybody and welcome to Conversational Selling. This is the podcast for sales leaders, business experts who will share what’s working now in sales and marketing. And it all starts with human conversation. I’m your host, Nancy Calabrese and I’m so darn excited to welcome Darryl Praill, who is the Chief Marketing Officer at VanillaSoft, industry’s most established sales engagement platform.

He’s an award-winning marketer, Sales World top 50 keynote speaker, a 2020 Top 10 SaaS branding expert, radio broadcaster, podcaster, social media influencer who has his own website. He’s raised almost 100 million in venture capital and is just a down to earth, crazy funny kind of guy. Darryl, welcome to the show. And I gotta ask you, do you ever get a chance to breathe?

Darryl Praill: Sometimes. Sometimes when, my wife is very good at making sure that I take time out. And it’s a constant battle she and I have because she’s like, you know, me time, I need you to put the phone down, put the tablet down the computer down, spend time with me. So she’s very good at making sure that I shut off on occasion. But otherwise Yeah, it’s been crazy. And you made me laugh with that intro. The best part of the intro is when you said I was down to earth. My blue collar roots would thank you for that. That’s awesome. Thank you so much.

Nancy: But you are. You’re very relatable and I know my audience will, by the end of it, will know what I’m talking about. So why don’t we intrigue everyone and tell me something that’s really unique about Darryl Praill and also VanillaSoft?

What’s Unique About VanillaSoft and Darryl’s Personal Brand?

Darryl: Sure. Okay. So if it’s about Darryl Praill,  what’s unique is only, you know, I’ve had, this is unique, it’s gonna sound counterintuitive. I have had the success I’ve had in my career by being incredibly uncomfortably awkwardly vulnerable and transparent. Which you’re saying, well, Darryl, you’ve won these awards, you’ve raised a lot of money and that’s a lot of power brokers in a lot of rooms.

How can you do that by being so vulnerable and transparent? And the reason is because people look at you a couple different ways. They say, Wow, you’re that vulnerable and transparent and don’t mind sharing it, they must be really confident, or they’re really relatable. You made the comment.

Or, you know, therefore I connect with this individual. I trust this person because if they’re willing to share their worst, then, you know, I feel like they’re going to be straight with me. So, being vulnerable and transparent is my secret sauce. Just put it out there, ask me any question, I have made more mistakes you can shake a stick at but I’ve gotten smarter along the way. As for VanillaSoft, VanillaSoft is a sales engagement platform. And what that really means is we allow your sales team to make more sales calls to have more conversations, actually then close more deals.

And we automate that whole process with us using the phone or email or social media or SMS text. So your reps are making a gazillion outreach touches way more than they ever possibly could. What’s pretty cool about that is it overcomes the one issue that every rep is guilty of doing which is kicking them in the behind, which is they cherry-pick their leads. When you cherry-pick, that means there’s a whole bunch of leads you’re not calling because you skipped over them.

What’s cool about VanillaSoft, what’s unique is we have this what we call a queue, and the queue doesn’t give you a list. It just says this is the next leads column. And it’s just like a queue. And the queue always recalculating. So something cool happened outside, somebody filled out a form on your website, whatever it might be. It’s serving you the next best lead at that moment in time, eliminates cherry-picking. And that’s a big reason why it’s successful. So the queue is what VanillaSoft in being vulnerable and transparent is about me.

Nancy: Yeah, well, you know, first of all, transparency I think goes a long way in developing business relationships because it’s all about connecting and learning to trust. And for those of you that don’t know we, at One of a Kind Sales, have been avid fans of VanillaSoft, and we’ve had an amazing return on our investment. So I highly recommend that you check them out at vanillasoft.com. Crazy question, though, Darryl, where did you come up with the name VanillaSoft?

Darryl: We get asked that question so much. It’s Usually we get asked the question of where did it come from? Or are you married to that name? Are you gonna change it? So it’s one of the other. And honestly, there’s no story. I genuinely, I have asked, I have asked, and no one really knows. It’s lost in the annals of time. I do not know where it came from. But the reason we keep it is because it is distinctive, and it’s memorable. Whether you like it, or you don’t if you want to call it ice cream, I’m indifferent. You will remember the name, and that’s why we have it.

Nancy: Awesome. Awesome. So, you know, for our folks out there, I know you talked about sales engagement platform. As often, I get asked the question, well, what’s the difference between that and a CRM? And maybe you can explain that.


Darryl: Great question. So there is a lot of overlap. And in fact, roughly 40% of our install base consider us their CRM. So let me make it real simple for you. CRM as a whole is about the whole customer experience. So it’s about selling to them and then on onboarding them and then providing customer service and support. So that’s a full lifecycle, right? Where sales engagement is just part of that, which is the sales part. That’s all it is. So you would never use us to onboard a client, you would never use us to do the ongoing sales and I’m sorry, the ongoing support and service of them.

The CRM is the whole backbone, sales engagements, just the sales side. For many, one last differentiator is sales engagement typically doesn’t have a concept of a sales opportunity or a sales forecast, where CRM does. They’re all about managing the opportunity so you can have a pipeline. Sales engagement, but like I said, 40% use us as a CRM because they have, their sale is not a complex sale, therefore it’s very transactional and they don’t need a pipeline to close the business now. So for them, it works wonderful to use us as that one-stop-shop. Keeps their costs down and keeps the reps productive.

Nancy: Yep, I get it. And for most of our projects here, we use it as a CRM. So again, everybody out there, I would highly recommend you go check them out at vanillasoft.com where you will also find an article that was recently published. Darryl published Sales In the Age of Social Distancing, and whatever the Hell is Next, which I thought was a pretty catchy title. Two things that were stated in the article, I’m hoping you can expand on it. You open it up by saying that best medication for tough times is more pipeline. And the second point is, hey, sales pro, you’re never above cold calling. So why don’t we tackle the two of those statements?

Pipelines and Cold Calls

Darryl: Well, it’s interesting, right? So it’s true. A pipeline solves everything. Wouldn’t we all agree with that? I mean yes, you have to close it ultimately, but a pipeline solves everything,  even in bad times. So what was kind of interesting was when COVID really started hitting, you know, we were seeing stats from Toko, from Gartner from HubSpot, where they were saying deal sizes were and new deal creation was dropping 30, 40% relative to historical norms. So that, boom. But what was interesting on our VanillaSoft platform, the most we ever saw the actual activity drop was 7%.

And that was only a couple of weeks, it bounced back to almost, you know, historical realms. Which means that people were just trying that much harder. They never stopped with the activity to make the pipeline. You know, yeah, deals are slower. That’s the issue. So pipeline solves everything. You just do that. The biggest thing I want to say to you if it’s a COVID situation, it’s not that people aren’t buying, it’s that they may not be buying what you were selling historically and you may need to pivot. So in our case of VanillaSoft, we have a large install base and like the services side, hospitality side.

We had to fundamentally say we’re here when you’re ready to come back because we recognize you have no money right now. But boom, insurance is on fire because everybody going Oh, COVID, do I have property insurance? Do I have life insurance? Do I have end of life insurance? So they went on fire. So we pivoted. So it’s a combination of pipelines loves everything, we gotta be smart about it. So just don’t keep on doing the same old same old. That’s the first part. What was the second part? Remind me.

Nancy: Second part, never above cold calling. Sales professionals just get to a point and they say, Well, I don’t need to do this anymore. It’s beneath me. So what do you have to say that?

Darryl: I see you’re doing yourself a huge disservice. And this is why. Times change. So can you imagine selling now versus selling six months ago, right? The sales cycle has changed dramatically. If you’re not calling to your audience, you’re not hearing the latest and greatest objections, pushback. You’re not hearing who the most recent competition is. You’re not hearing the objections that the users are giving you that they might not have given you before. You need to always be dialing just so you’re fresh.

So you understand the angle. So you’re refining your message. The same reason I said you need to pivot when you’re dialing your activity because, you know, pre COVID I might have been over here, services, hospitality. You know, but now am I’m in it? I’m not. I pivoted. That’s the same reason your dialing. You know, what message still works, what message doesn’t? What helps you advance an opportunity and what you shouldn’t be saying to stop an opportunity in its tracks? Dialing is not a thing that should be beneath you. Dialing should be your competitive advantage.

Nancy: Yep. Well said. And I totally agree. Now. You are a marketing expert. And from what I’ve learned about you, you’re passionate about it. How did you develop your own personal branding?

Darryl’s Insights Into Building a Personal Brand

Darryl: The personal brand is an interesting story. Cause and effect. So I had a situation where I had been hired for a company many years ago, mid-2000s. And I had a three-year mandate to flip them. The CEO was brought in, he hired me. So he and I were brought in to flip this company within three years. We did it within nine months. It was a wonderful story. We took, we went from number three to number one in the marketplace.

And then the acquiring company acquired us because we were on fire, and they wanted the team because we were doing such a great job. Fast forward 30 days, boom, the whole team was let go. I know. It’s a story we’ve all heard before, right? So here I am never ever having been out of a job before, always being recruited and I didn’t see this coming. So if that happens to me, and this is what I do for a living, it can happen to everybody.

So I realized then that it was the only person that would ever make sure I always had income, always had opportunity, was me. And so for me to do that, I needed to brand me. That was where it started. from. That’s why I have darrylpraill.com like on Twitter, and everything else, LinkedIn, etc. And it wasn’t just, I put a profile up there and then I never touched it again, which I was guilty of. So that was the first part to make sure that I stood out from the crowd. I made content, I made blog posts, I made videos, and that was when I really got my game going.

And I knew it was working in that situation. I actually went and targeted 11 companies and I reached out with my personal branding tactics, I got seven interviews and I got four job offers. That’s when I said, Holy smokes, this thing works. So then fast forward to now right? We’re in the year 2020. And it’s the age of social media, the age of everybody has a voice. How do you get heard when a very noisy environment. And that’s where the personal brand is everything. It’s no longer the age of the company.

People aren’t necessarily buying from One of a Kind Sales, they’re not buying from VanillaSoft. No, they’re buying Nancy Calabrese. They’re buying Darryl Praill. That’s who people buy from now. The personal brand is everything. You got to make that investment. And it’s not easy, but it’s actually a lot easier than you might expect. The only thing holding you back from doing it candidly cuz I’ve been here, it’s just you’re worried that you’re going to, you know, have nothing to talk about, you don’t have the time, you don’t have the insights.

You’re afraid of getting mocked on, picked on, abused, social trolled, I get it all. Those are all just excuses. They’re going to happen regardless. Throw it away. Remember I said be vulnerable and transparent? Lead with that. You know, yeah, you’re probably gonna pick on me. That’s okay. Here’s my point of view. Because the people that care about you, they’re going to check you out and they’re not going to read what the trolls say. They’re going to look at what you say and they’re going to buy from you.

Nancy: And by the way, for all you folks I know you can’t see Darrell but he also brands himself with a variety of eyeglasses and sometimes that real funky hairdo. So definitely go check him out. And that’s a good segue actually. Tell my audience about your podcast.

Inside Inside Sales

Darryl: Sure. So the podcast is called Inside Inside Sales. We have to say right. It’s Inside Inside Sales, right? We got to get the voice going. And that’s what we did. We get inside the whole process of selling when you’re not an external field rep. So it could be could be a sales development rep, doesn’t matter.

You’re inside sales. And we just get into the actual do’s and the don’ts. And we’re not talking vision. There’s no vision talked about. We’re not talking management speak. We’re talking pure selling. How do you discovery? What’s your opening seven to 12-second line? How do you do objection handling? How do you use an open-ended question versus a closed-ended question?

How do I use social selling? How do I stop the pitch? How do I get past the inevitable No? It’s all these how to’s. And the whole goal is to make yourself just 1% better. And we have like the who’s who, in the industry. We’re so blessed. Spend time with us every single week. So just go to insideinsidesales.com. You’ll see all the guests, and Nancy is going to be on there soon. So look out for her podcast.

Nancy: Can’t wait. Look out for us. So we’re almost out of time. And I’d love to continue this. But let’s just end with two questions. So what is one takeaway you’d like to leave the audience with?

Darryl: I go back to what we talked about earlier, your personal brand is going to dictate your success, all right? So if you’re not sure how to do it, if you’re scared, if you’re uncertain, reach out to me. Connect with me on LinkedIn, I will hold your hand, all right? Because I want you to succeed and it’s really really, really, really easy. And you don’t need to have a gazillion followers to have a personal brand. It’s way easier than that. Make the investment in you. It will pay huge dividends.

Nancy: Awesome. And how can my audience find you?

Darryl: You go to darrylpraill.com. DARRYLPRAILL.com. You can go to LinkedIn. I’m all over LinkedIn. Go to LinkedIn, you’ll find me. And usually, the guy who’s in a fight or a debate with somebody on some issue because that’s the beauty of LinkedIn, you can do that. I’m on Twitter. My Twitter handle is Ohpinion8ted. OHPIN8TED because I have opinions. And, or you could just email me. Go to vanillasoft.com. My contact information is there. Just Google me, you will find my name. I guarantee it.

Nancy: Well, wasn’t this great, audience? I am so excited to have introduced you all to Darryl Praill. I hope you take advantage of some of his wise insights into the wacky world of selling and marketing. Stay strong. Stay safe everyone. And thank you, Darryl, for making this an awesome conversation.

Darryl: I had a blast.