From CMO to CRO, Sales and Storytelling, Marketing Bots | Darryl Praill @ VanillaSoft

February 2, 2023

Episode Description

Darryl Praill, CRO over at VanillaSoft joined me for today's pod. We go in depth on his rationale to make the switch from CMO to CRO, his philosophy behind the importance of all marketers also being sellers, and he might have spent a few minutes on his latest soapbox about marketing bots. (Isn't AI great all the time though? No way it could possibly provide an unauthentic experience...) Happy listening! See ya on the other side ✌️

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About Demand Gen Chat

Demand Gen Chat is a Chili Piper podcast hosted by Kaylee Edmondson. Join us as we sit down with leaders in marketing to discover the key to driving B2B revenue. If you want benchmarks or insights on trends in the market, this podcast is for you!

Episode Transcript

Hey everybody. Welcome back to another episode of Demand Gen Chat. I'm your host Kaylee Edmondson, and today we are so thankful to be joined by Darryl Praill, who is the CRO over at Vanilla Soft. Um, interestingly enough, CMO turned CRO, so that seems, uh, like a hot topic I'd love to start with. But can you tell us a little bit more about yourself and kinda how you landed this gig at Vanilla Soft?

Before I answer that question Kaylee I want you to know, so if you c- if you're watching the video, this is, this is the Demand Gen Chat. It's, it's on my podcast, on my player. I listen to Kaylee all the time-


... and, and now I'm on the show. Mom, I've made it. This is so cool.


Um, so, uh, you, [laughs], you, you asked me a question, the question was, how did I get this gig? Or was it something else? It was, yes, it was, how did I get this gig?

Yeah, yeah, yeah. I wanna know how you got this gig.


Yeah. But 'cause you started as a CMO and now you're CRO.


And obviously I feel like that required some type of jump from the gate. But-

How the hell did that happen? Yes. Were they drunk? [laughs].

Right. I need to know how it happened.

This is-

Sure. [laughs].

... they had no 'cause marketers make no money. Um, yes. I understand all the above. Okay. Quick and dirty. Uh, I began, again, a little, little bit of background 'cause it's relevant.

Mm-hmm [affirmative].

I began life-

Mm-hmm [affirmative].

... as a computer programmer. All right. That's my education. I know, it's crazy. Um, and when I finish school, I'm like coding, I, "Who wants to code anymore? That's so stupid. That's boring, sitting behind a monitor. What do I do?" And then, friends, everybody said, "You should go in sales." Now when you're 21 years old, you have zero idea what the hell that means. "Sure. I'll go in sales." And I started selling photo copiers, door to door, for six months. And if you want to have any iota of confidence or self worth, um, stripped away from you immediately, do that. Sell photocopiers door to door, go knock on the mechanic store, go look on that one lonely accountant in his little office, go look, uh, you know, at the HVAC place, in the roofing place, in the construction place, uh, it's great. Let me tell you. That was my first sales job.

Learned a lot, went back to coding. Fast forward five years-

But you only left in six months.

Six months. Yes. Because-

Right. [laughs].

... and I even bought a car for it, Kaylee, I bought a minivan. How c- ... 21 and a minivan, because I needed to be able to bring the, the copiers to show them how awesome this was gonna change their life. So I, I, I, I, I had a maroon minivan with a sliding door, Plymouth Voyager. I was the catch male. Thank God, I was already engaged at that point in time, I never would've got another woman in my life. So, um, so I went to coding and then after about five years, I was like, "Okay. Um, enough of this." And, and I, I, I popped out into sales, I became a sales engineer and I moved to the States and I became a sales engineer for a high tech company.

Uh, sales engineer led to product management, led to product marketing, led to marketing. And then you flip jobs, you're going back in sales, because, it was a sales and marketing role, smaller companies. And so, before you know it, I'm a first time VP of marketing at 29. And I was a VP of sales and marketing by the time I was 34. Uh, and I, so I've been a VP of sales or a VP of sales and marketing three times previously, and I've been a VP or CMO three, four times previously. [laughs]. And I've had some good success. But I liked marketing and I, and the reason I liked market anymore was 'cause it didn't have that constant pressure of a quota.

So I said, "I'm gonna be a CMO that's my gig. I'm, that's where I'm going." Yes, you, you know, you know, it, it's painful.


So for the last 10 plus years, I was C- I was a CMO and then I had my own agency for eight of those years. And then Vanilla Soft came knocking, and it was such a cool technology sales engagement, for who don't know, we'd be in the same category as vendors like Salesloft or Outreach. The same thing, different markets, but you get the idea. Hot, uh, I've been in the tornado before, I know what to expect. And I, I we- I le- I close the agency to take this job, but, you know, so I've been an executive multiple times so I understand, you know ... I've raised over a hundred million dollars, I've gone public twice, I've been sold twice, I've been fired once. So I understand what's involved to be an executive and I understand about EBITDA and the Rule of 40 and all that wonderful stuff.

So, you know, about a year and a half into my gig in the marketing side, I could see that we had certain and goals for sales and we weren't necessarily achieving them. And I did what every marketing leader should do, is I went to the CEO, and I said, "Listen, George boy, not his real name, uh, part of my compensation is on company revenues and I make these amazing MQLs and I give them to sales and they don't call them or they call them once. Or they call them, and have you heard the recording of that call and how fricking awful it was? And that's affecting my take home pay and I'm not really that happy about it."

And after a period of time, you're right, we put in programs to try to fix that. Fast forward another year, not making the progress we'd hope to, wonderful leadership, love them, but , you know, the results were the results. Lots of reasons why. And finally I said, at that point in time, I said, "Hey, if you ever are thinking making a change, because that's the next step, it's inevitable, we've seen it over and over again, I would like you to consider me." And the CEO laughed at me, literally laughed at me.


"Sure Darryl, you ... And I said, "Dude, I've carried a bag, [laughs], I've been a sales rep, I ... "Darryl, that was so long ago, like, yeah, right. You're the marketing guy." And I'm like, "Okay, whatever." And then I just kept on, uh, you know, during deals and reviews, I, I would often know the numbers better than anybody else. I would often know the deal status better than anybody else. So when the time came, that they finally wanted to make a decision, they themselves got some outside advisors. They talked to the board, the CEO, and they kind of came ... This is what it was told to me. They came to a decision of, "We could hire a VP of sales, it will take them a year to get up to speed, and the reality is Darryl's a strong personality. And so, Daryl will probably, this is their words, not mine, rule the roost."

Uh-huh [affirmative]. [laughs].

So, or we could take Darryl and put him back into sales leadership role. He has done it before, it it's been a while, and it'll probably take him three to six months to get up to speed. Um, but he's already got the respect and the reach and he knows the tool and he knows the processes. He knows the workflows, you know? So candidly, the better decision was that. So they offered me the job. I didn't take the job immediately, which was spirit art desire, right? 'Cause I was asking for it. Uh, that, when someone asks you, offers you a job or offers you a promotion, that's when you say, "Now's when I ask for everything I want, because once I take the job, I'll never get that chance again."

And so my-


... my, I, I didn't focus as much on, "Gimme a big fat pay raise." I said, "You know, gimme a modest pay raise. I'm fine with that." Um, I instead said, I had three conditions. I wanna be able to hire any rep anywhere in the world. Number two, I want to build a Rev Ops team and head count. Three, I wanna build a sales enablement team and head count. And they s- remarkably, they said, "Okay." And then I took the job and that was July 1st, 2020 is when I began the new role.

Wow. Okay. So I have a lot of follow-up questions for that.

Do it.

Um, your three requirements, so are these things, I guess, that were drastically different from the way that Vanilla Soft was operating, while you were in your CMO role. Like reps weren't anywhere in the world, you didn't have a Rev Ops team and you didn't have an enablement team at all.

So reps were all hired in our Plano, Texas, Greater Plano, Texas, Dallas, Texas area.

Mm-hmm [affirmative].

That's where our us head office is. And, uh, 'cause the idea was we wanted the pit environment where we can learn off of each other. And, oh, I had a great call and there's a leader board, you know?


And, and, and there's a lot to be said for that. So that was the, the, that was what we did historically. There was no Rev Ops team marketing, me and my crew and the marketing team just, just did it. Oh, you, we want HubSpot, we're getting HubSpot, uh, we'll do it. We'll pay some consultants and we'll do it ourselves. "And Joey, you've never done Rep HubSpot before," we suggested for some training, "And now Joey you're the HubSpot person, on top of doing copy writing and emails and everything else."

And uh, and oh, we wanna do, you know, another tool or let, let's let's have CAST IT for our podcasting platform or let's, you know, whatever. Bing, bang, boom. So what I wanted was, if I was gonna own the whole revenue organization, I wanted a stack that was uniform across the organization that allowed me to give, give me a, a lifetime end-to-end view of the buyer's journey, the cost of acquisition, deal velocity, all this stuff. So to do that, you get to a certain point where, you know, we were ... So we, we didn't have, we didn't, at the time, we didn't have conversational intelligence, we didn't have a sales and enablement platform, right?

Mm-hmm [affirmative].

Et cetera. So we, I know we need, if we're gonna have a reputable, scalable sales team, to hit the numbers we wanted to hit, which is what wasn't happening before, we needed to equip the team, which meant, I needed a handful of people who were focused on just giving me two things. An infrastructure that was robust and, and protected the reps from doing stupid things that reps like to do. Like not putting in close dates or opportunity values-

Mm-hmm [affirmative].

... or what have you, or even updating accounts and opportunities. Um, but number two gave me all the data and the information and the stats I needed to make informed wise decisions as opposed to gut feeling. And we had a lot of gut feeling before.


Finally, on the sales and enablement side, the VP of sales did a lot of that coaching part of their job. Uh, and we had team leads, they did it as well, but again, that wasn't scalable. So every time we had a new rep start, those people were doing one-on-one coaching, where I wanted actual-

Mm-hmm [affirmative].

... you know, you know ... I, we, we invested in Seismic, we invested in Brain Shark, I hired a, a dedicated sales trainer to do nothing but sales training content. So when people came on board, we just ramp 'em up in a scalable, repeatable controllable fashion, um, and we could optimize that for every iterative hire. In that way we could get a faster ROI on their, on their return. In other words, they could be making money for me in the first, you know, 60 to 90 days as opposed to six months to a year. So that was-

Mm-hmm [affirmative].

... it was all about efficiency and scale.

Yeah. No, I love that. And I'm curious to know too as well, like just how you, um, have built out your Rev Ops function, specifically in relation obviously to Demand Gen. Um, I feel like, at least in my experience or tenure, um, Marketing Ops almost always like somehow becomes a part of a Demand Gen function, probably because of job security and need to confirm that the dollars you're spending are actually driving revenue.


Um, but obviously with this new, newer emotion of creating a centralized Rev Ops team, it's critical that those two teams are in lockstep all the time, right? And now with them all like rolling up underneath your leadership, I'm sure that creates some synergies in and of itself. But as you were building out this Rev Ops function, how did you think about the hierarchy of that team? Like, do you have a dedicated person on that team that is the liaison between marketing and Rev Ops and then a different person that's like the Sales Ops liaison or is it like principle-based, based on like projects or disciplines?

Okay. Awesome question. Um, where to start. So it was an iterative process 'cause we were building out the team. So clearly the marketing, the, the, the existing Marketing Ops person, uh, who again was pretty part-time, kind of started the process. But the first thing I did-

Mm-hmm [affirmative].

... was in fact, when I took the job, so, and I'm not lying, so I had, I had a number two guy, uh, on my team. When I was CMO, I had my number two guy, who was my right hand person and helped me do some amazing stuff, completely different from me. This is really important. My job, if you can't tell already listening to this podcast, is to be the face of the company, which means I get to talk loud and, and, and be obnoxious and mock myself and have spiky hair and wear annoying glasses. Just so you'll all remember me-


... that's called branding kids. Um, this fellow was, I call him my Savant, it sounds stupid but, he was process, he was workflow. He knew every bit and, and, and, and if I do this here, that happens over there and he understood benchmarks on best in class marketing metrics. And he would look at every single campaign we did, and how did that perform versus historical versus, you know, industry? What's our return on that? You know, he put in a whole common data platform, so we could do all lead tracking and, and, and analysis. That's him. Ask him to do what I'm doing right now, he would crawl on a corner and cry, even though he's a rockstar marketer, not his strength. So we compliment each other well.

So when I got the job, literally the first call I made was I called him up and I said, "Dude," and he said, "Yeah." I said, "This is what's happened. I've been offered this job. I'm doing it. And I need a staff, the Rev Ops role. I would like you to move and run that team and build the team out." And he was like, "Uh, uh, okay." And so he had no experience, but I knew he had a ton of experience 'cause he knew how I worked, he knew how marketing worked. Uh, he knew, because I knew the sales numbers better than others, that was probably because of him.

Mm-hmm [affirmative].

So he was the right guy. So he and I built it out together. And what we did was we crafted a vision, we wanted our platform to be. And then we had a budget for it, so it probably took us a good year to get all the bits and pieces we wanted to. 'Cause every one of these pieces are expensive, as you understand-

Mm-hmm [affirmative].

... and you have to negotiate and you kinda have to say, "Okay. I'm gonna go invest in ... I can't tell you how many times I, I have a conversation like, "Hey, we're gonna get Brain Shark." "Well, why do we need Brain Shark?" "Well, we need brain shark because of this." "Well, yeah, but, you know, can't we just use Trello for that?" Not necessarily a bad question, and you have to have an answer, so you have to stagger the budget. And so, we put together the plan-

Mm-hmm [affirmative].

... and then what we did was we started ramping up. So we actually initially started off with some part-timers, uh, who were just keen to get in. And uh, and so, and then we took from that, we got a little creative. You, you'll like this one. So we have a series of people. We have four people on team, um, and every single person has got, uh, ownership of specific, specific, um, pieces in the sack. So one, we have two people who are certified now in Salesforce, we have one person who owns [inaudible 00:14:34] and they own, you know, Zoom and they own, you know, all the other odds and bobs and sods. All right.

Then we have one person ... There should be five people on the team, sorry. We have one person who owns HubSpot, right? And they're the Ops person, in, in the sense that they own anything on, Data management, landing pages, email, et cetera, all the users. And so, we have all these people, and then of course, all the actual, uh, marketers, if I'm doing an email or, or I'm doing a landing page, they can go in and actually make it themselves. And then the overall HubSpot person and the Rev Ops team would actually make sure it's all cool and on the right process. So it's an, an approval process.

But where it gets interesting is this, this is what I did. So this is a case of managing your budget kids. I know I needed this team, but I also knew I needed sales engineers. We didn't have any sales engineers, uh, every single one of our sales reps was meant to be an expert on the, on the product.


And that's where I was working. And the problem with that is, you go into an enterprise say, and then you get on with a big buying committee and they say, "Well, this is our situation. We have 42 products and they're all working real-time and we've got Zapier and we've got Native Integrations. And can you tell me how to integrate your products so that it only works on a full moon, but only in Greenwich Mean Time, and only by employees, subcontracted out of India, show me that?" All right. And the sales rep would go, "What the F?"


So I needed sales engineers. So what I did was I actually took two of my rockstar, customer support people, who wanted to become customer success people, but there were no openings there, and they were ready and I brought 'em in to be sales engineers. And then I did this, and this is the part that I think is still inspired. I said, "You're gonna be sales engineers, but you're gonna be asked questions about integration, which you need to answer. Therefore, I'm gonna second you on a matrix organization to Rev Ops. Any integration we need done for our, our Rev Sta- our Tech Stack, you are gonna do. And that way, when you're on a sales call, you're gonna say, well, yeah, you can do that. In fact, let me show you how we integrate this."

And literally, we were on a call the other day, where, as a good example, it was a prospect out of Australia, and they said, "We have Salesforce, we have Chorus and we're evaluating Vanilla Soft. And we wanna know how the three work together. So, and we also wanna know about Vanilla Soft." So the sales engineer with the AE got on the call and they said, "Okay. We're gonna give you a little, a little bit. Here's like, you know, 10 minutes on Vanilla Soft, just the basics. Okay. Now what we're gonna do, this is after discovery, now what we're gonna do is we're gonna park Vanilla Soft for a second. And 'cause what you're really asking about, you said, you wanted the integration, what you want is the workflow. That's what you want."

And they're like, "Yeah." "We're gonna show you our workflow. I'm gonna re- you know, and, and here's how it works between all three of this, you know, products." So when you're doing that solution sale, that could never have happened if my sales engineer wasn't involved in a Rev Ops team because they've done it themselves first in hand. And they are accountable to my sales reps and to me and to the marketers, as their customers. So that's what we did to make our budget work. I'm not sure I answered your question, but it was a good story.

No, it was a great story. I think you answered my question. I was just super curious as to, yeah, like how you've built out the disciplines with your Rev Ops team. And I think like, I got it, hopefully listeners get it. I feel like I have a full view of what's happening there. So my hot take question for you is this, now that you're all warmed up and riffing on everything, [laughs], should CROs, and, uh, you're different 'cause I understand you're both, but you were a CMO before you changed over to the CRO side and started managing both. Are more successful CROs going to come from a CMO marketing background or a sales background and why?

Easy answer. Easy answer. And I'm not saying this because of my background-

Uh, it's not easy according to marketing ... It's not easy according to marketing Twitter though. Marketing Twitter is like fired up about it. So I just need your hot take.

Okay. So the answer is, is an easy answer but there is a caveat, I'll give you both. Okay?

Uh-huh [affirmative]. [laughs].

Okay. So the best CROs will come from marketing because most of selling today is a combination of, tell me if this makes sense to you, uh, Kaylee, automated sequences or cadences done through sales engagement platforms or bots. Which is all about messaging and personalization, call to actions, compelling content and measuring the data to know what performs better and continually AB testing. Everything I just said there is marketing, isn't it? Yeah. That's what sales reps are doing. I literally, about a year ago, we sent an email blast out, my name is on it. It was probably saying, "Hey, are you subscribed to the Demand Gen Chat Podcast? 'Cause Kaylee rocks, you should." And, and I got a response back from SDR, saying, "Your subject line sucks."


"I have, I have an 84% open rate, and uh, if you want my help on how to write an email that works, let me know." And I, so I'm getting this and I'm open and I'm reading this-

Oh, wow.

... and it was like an epiphany moment, for many reasons. My initial reaction like any marketer was like, "Nobody in the world has an 84% open rate. So the fact that you think you have an 84% open rate, shows you how entirely and utterly clueless you still are, Mr. Sales Rep, and you need some serious help." But that aside, where Rock My World was, this sales rep, the sales development rep knew their open rate, at least, what they thought was an open rate.

Maybe. [laughs].

And had an opinion on my email that followed total best practices. And for the record, I don't remember the numbers, but I do know, 'cause then I was curious, that particular email we sent out had a massive open rate. So I knew everything was cool, we did the numbers. So that was a game changer for me. And that's when I s- I finally realized, the CROs are gonna be coming from the CMO side because the lines are blurring so much and, and buyers are self educating, and often many account rec, uh, execs are ... Don't yell at me Kids if you're in a AE, many of you are becoming order takers. All right. That's the, the fact of the matter.

Mm-hmm [affirmative].

Here's my caveat. You still need to understand sales. And too many marketers are scared shitless, excuse the words, of that sales world. And they've never even picked up a phone in their life. They have an opinion, which is remarkable, because I don't know how you could have an opinion without ever doing the task, not even once. So if you wanna be CRO, you still have to do the job. You can go ... I don't know, maybe swa- do, do a, a swap, you know, instead of a house swap, you do at a sales and marketing employee swap. And you sit in each other's chair for a month. All right. And watch that sales rep struggle to write email, copy or website copy that works or do any kind of content that converts and watch that marketer, uh, realize that it's painful and it's full of rejection and you get hung up on a lot and people yell at you and people have an opinion.

And when you get 'em on the call, you get tongue tied and they ask you questions, you don't know the answers. You feel like a dumb ass. So when you live that life for a while, all of a sudden you go, "Okay." And then the next thing is, and this, and, and by the way, what I'm about to tell you applies, not even if you're a CRO, if you have aspirations to be a VP of marketing or a CMO, what I'm about to tell you still applies. You need to know the data on sales and sales performance and sales conversions, and the state of every single major deal better than your sales counterparts. 'Cause you will only get the respect of the executive table, if you do that. And then you need to insert yourself where relevant to help close the deals, stop waiting for your sales counterparts to do it on their own.

'Cause you're at the executive table, you are all working together to achieve revenue. You just have different jobs. If you don't know the numbers, you don't know the math, you don't insert yourself, you don't talk to the sales reps, which by the way, your best messaging comes from talking to the sales reps.

Mm-hmm [affirmative].

Either you're gonna learn that they're not saying what you're saying, or they're saying stuff that converts way better than what you're saying. Either way, you gotta get that under control. So that's the caveat. If you wanna be a good CRO, marketers, you know, put your foot in the sales pond for a little bit and have a clue and know the numbers, but from pure raw selling, marketers are already selling. We're doing touch free selling. We're getting you, you know, we're, we're refining, you, we're targeting you. We're we're, we're enticing you to come to our site on inbound. And then we're working you through the sales funnel. We're being intelligent with the content we share. We're personalizing it based on Persona on it and based on ICP. We're being very intentional with our nurturers, we're qualifying you. We already get it. So we have way more of the skills than just sales reps do. And that's why.

Hmm. I feel like that was good though. Very thorough answer. Um, maybe, uh, what I knew you were gonna say to some degree that, I knew you were gonna lean towards marketing. But, no, I think it's a good ... I mean I've never done sales, I'm a, [laughs], I'm the kid you were just speaking to that's terrified to do sales, that's for sure me. Um, I'm pretty sure Chili Pepper will never let me do sales here for 30 days, that would be detrimental. [laugh]. But, um, getting close with your sales team, yes, relevant, talking to them, for sure. Not only are they sometimes not saying the same messaging that we are on the marketing front, but they have this, obviously, constant feedback loop to the market. Because they're getting on sales calls all day long in and out, and people are describing our product to them, in a way that makes sense to them. So they are hearing like direct feedback from the market that we, in marketing land, don't have access to until we got gong.

Um, but even still, it's just not at the same scale. Like, I can't listen to gong calls, you know-

All the time.

... 150 gong calls a day. It's just like not gonna happen. But it's still more helpful than we were doing before, which is basically like, they have an ear to the ground, so to speak, and we have nothing. Um, and so yeah, obviously like they're not saying the exact same thing we're saying, because they are hearing directly from the market, how people are describing our product or how people are describing their pain point or what our value properly should be. And over in marketing land, we're just over here like, "Oh, words, let's put words that are cute, fluffy, sassy, whatever, that fit nicely on the page."


And that's just like not always how it needs to work out.

But here's a, a, a c- uh, what's the word, a, a contrarian point of view to what you said a little bit. I have found often marketers-


... are better sales reps and this is why. One of the most powerful aspects of selling to be successful is storytelling.




So sales reps are at the front-end of the sales process, so they're talking to prospects who are not yet customers. So they're hearing their story and their pain and that's great. And we can learn from them so we have the right buzzwords and messaging to, and, you know, get them to click through and become inbound. But as that deal progresses and the buying committee expands and they're talking to different stakeholders, that's where marketers get better and sales reps don't, and this is why. Marketers are the ones writing the case studies.

Mm-hmm [affirmative].

Marketers are the ones talking to the industry analysts. Marketers are the ones taking the interviews from the media. Marketers are the ones who are going and speaking alternate industry events, often. So because you've talked to the customer, because you did a case study and because you talked to an analyst who told you what's going on, when you get into that sales cycle, you can now start to say, "It's funny, you said that Mr. Prospect, I was just talking with our happiest customer, ABC Inc and John DOE physically said the following thing, blah, blah blah. Now specifically John pointed out of how they had this problem, and Susie said how they had that problem. And what we were able to do with them, was pull together in a nice little bow. And what's interesting, 'cause Gartner said that that approached best, when I was talking to, you know, uh, Frank and, and Sarah. So that's our situation."

And I do this on a regular basis and my sales reps are like, "Where the hell are you getting all this content from?" Ironically, it's, it's all in seismic for us, it's all in our content database.

Mm-hmm [affirmative].

And if they listen to half of our podcast or they read their own case studies that we write for them, they would have all these anecdotes. But that's why marketers can often be better sales reps, 'cause they know the stories.

Hmm. Sure. And there's definitely power in storytelling and sales people just aren't, they aren't geared that way, right? Like you said 10 minutes ago, right? They're geared for quota, that's why you decided you needed to be a CMO.


'Cause you didn't wanna be held to a quota. [laughs].


That's all they're focused on, right? It's just like making sure that they can buy groceries this week.


Um, and so, they skipped over the storytelling component just to try and close deal and yeah, I guess that doesn't always work out well in the end.

No. And that's like marketing and sales to have that part in common, which is play the long game. So sales have to learn to pace themselves in sales-


... not to try to close it today. Just like, I mean, how many marketers have said to management, "Guess we're doing an ABM model. We're gonna roll that out." And by the way, you're not gonna see benefits of it for six to 12 months. "Or yes, we're doing SEO," but we're not gonna see an increase in organic traffic for minimally nine months that it's tangible. And they're like, "Why am I spending all this money? This is just Hocus Pocus. I don't need this, I need every, an immediate ROI."


So playing the long game, stop doing shortcuts, Huge. No matter what you're doing, sales or marketing.

Before we get to wrap, I have two more questions.

Do it.

One question is, um, obviously I did some research on your LinkedIn before we hopped on this call and I'm really keen on your latest soapbox, which seems to be bots. Um, and I feel like you have a bone to pick, so I would just like to give you the floor for a second to riff on your current issue or stance on bots and how they're affecting your life. [laugh].

No problem. So I, uh, here's the best way to put it. Um, where do I s- it's like, where do I start? Okay, so-

Right. [laugh].

... a little background. Um, so when I took this job as CMO, in 2017, I was 49 turning, about to turn 50 and LinkedIn for me was just my CV. That's all it was.


And, and uh, I, three months into the job, I had done the lay of the land and I come back and I said, "Okay. So these are our competitors, and by the way, our competitors have raised hundreds of millions of dollars on a c- total growth trajectory, uh, because of that, they don't have to make money, the, the buying share. So they have a, you know, five to eight year plan. And our business model was the complete opposite. We were about fiscal responsibility, making money, we had never taken any money. And so, what does that mean? And those are just two different models. They're just two different approaches. But as a marketer, what does that mean?

As a marketer, it means, I'm never gonna be able to outspend my competition. I'm never gonna be the platinum sponsor at all those events that they're at.

Mm-hmm [affirmative].

I'm never gonna be able to buy my way into speaking opportunities that they can, so how do I compete? So for me, the answer was, we needed a corporate spokesperson who had influence, and that was gonna take some time. And since no one is volunteering, I stepped up and said, "I'll do that." So over the course of these last four years, I've grown my brand fairly significantly, got a large following. And we saw the consequences of that very quickly within the first year, again, play the long game, the first year, dramatic influx in inbound leads and everything else.

Why does that matter? It's not, Darryl's great, this is just a strategy. Trust me. I'm an in- believe it or not, I am an introvert and I hate doing that. I'm not lying. I will go, after this podcast is done, I will go on a corner and rock back and forth until I rest up and get new energy.


So that's what I had to do to have success. Now, along the way, to do that, you establish relationships, you establish great conversations and you build your network and you build a tribe and it is each other are helping one another. You talk about, you know, what's going on in the Twitter marketing world, same thing, it's a tribe, you're having conversation, all right?

Mm-hmm [affirmative].

So that's the beauty of social. Now, if half of your interactions are now bots reaching out to you and saying, "Hey, Kaylee, are you still the host of Demand Gen Chat?" And you respond back saying, "Yeah. Yeah. My love. But we just had Praill and everybody else, it was great." And the next response is, "Great. My product is A, B, C, D, and E." And all of a sudden you go, "Son of a bitch. You bastard."


"I have this, I'm trying to be part of the tribe, I'm being open, I'm being receptive. I wanna build a network, I wanna help each other lift each other up, and you you're a freaking bot. And y- and that was, that first line was a trigger to get me to respond to you, you misled me. You had no care in the world if I was still the host of Demand Gen Chat, you just wanted to get me to respond and accept your connection request so you can pitch me your wears." Okay.

That's, let me ask you this Kaylee, when, when you go by software for your Tech Stack, do you want a partner who's there to work with you in the good times and bad? Or do you want someone to take your money and never talk to you again? I'm gonna guess 'cause you're laughing.

Well, I feel like this is a leading, I feel like this is a leading question.

It is a leading question.

One, [laughs]-

But I want your answer.

But, but, yes, obviously, I want a partner and, uh, uh, even more so, I'm just not gonna buy from your cold email, your cold call or your cold LinkedIn DM.


Like just not. Unless you just so happen to randomly trigger off that automation, like, the day that I decide I'm in buying mode.

Correct. Bingo. You s- you nailed it perfectly. So that means those bots are starting off our relationship in a very disingenuous way-


... that there is no partnership, and I understand transaction, and therefore, since you're basically deceiving me, I'm not gonna do business with you because that's not the foundation of a relationship. That's my first complaint. And my second complaint is this, you know, the tools are there to personalize. So whether it's Vanilla Soft or anybody else, they're, they're there to say, "Okay. Your next, uh, outreach is to Kaylee and it's gonna be a social touch, and here's our default template." Hey Kaylee, do you, are you the host of Demand Gen Chat?" But before you, but you need to personalize it and then hit send. Instead they're choosing to turn on the automation and just let it rip.

Mm-hmm [affirmative].

Okay. Kaylee, are we as marketers allowed to spam? I'm just ask you that question.


No. And if we spam, we don't follow CASL or CAN-SPAM or GDPR rules. We don't have an unsubscribe, we don't have our address that people can reach out to us in our little footer of our emails. Do our emails get delivered?

Nope. Blacklisted. [laughs].

No. Blacklisted.

That's just stuff that's passed. Yeah.

Exactly. So why is it that sales reps or sales organizations can spam us, but marketers can't, right? So that's my lament with bots.


They're, it goes back to people taking shortcuts to get results. And here's the irony that I know you will appreciate so much. When I, when I challenge sales leaders on this, I ask them this very simple question that, this is, and this is why every CMO will make a great CRO, when you do that, what's your conversion rate like? In nine days out of 10, they look at me with a blank face. "What do you mean?" How many people are actually clicking through and how many deals did you source from that? Versus focusing on personalization, show me you know, me and actually making it relevant and contextual, you know? Do I wanna do a, a ...

I mean, again, as marketers, what's best practice? Do we email a massive list of 40,000 people or do we create a list of 1000 or 2000 on this segment and that segment and that segment and personalized the mess?

Mm-hmm [affirmative].

The same thing. That's my lament with bots. And too many sales reps don't want to give up the bots because the, if they don't use them, then that means they actually have to work. And there you go. I'm just trying to teach sales people how to be better salespeople.

Well, I really hope that we have a decent amount of salespeople that listen to this podcast. Um, but if not, I do feel like marketers will still resonate with it. Um, uh, [crosstalk 00:35:11].

Every marketers should be going to your sales team and saying, "Are you doing that?"

Yes. It's what I'm saying.

"'Cause if you are, you're killing my brand that I spent millions of dollars to build."

Right. Because, even, even so, um, I've worked, uh, for other companies in the past where sales reps did operate like that. And who do these people reach out to and share screenshots of it to? Marketers. All of the prospects that are receiving these like insane emails that aren't personalized from like a different title every three months. Like clearly they've just been like round-robin to a new like rotation every quarter or whatever your frequency is. [laughs].


They just have a thread in their Gmail that's the same copy from a different face. Like once every so many days. And then you, like I get a screenshot of it. "Hey, what is your sales team doing?" And I'm like, "I don't know. Like, I don't understand what's happening." So-


... I've definitely been on the receiving end like that, and there's like nothing worse. Because it's like, "Oh cool, well, I'm spending just a shit-ton of our company money, to try and create a good face and a good brand and meaningful content that actually matters, and it doesn't matter."

And I'll go even one step further to support exactly what you're saying. What's the worst thing that we marketers fear and happens? Somebody says, "I just got an email from Kaylee's company. Here's a screenshot of it. These bastards are wasting my time." And all of a sudden Kaylee's going, "How the hell do I combat this from a PR opponent?"


Right? So then one thing I would tell every marketers is you listen as we talk about this, and, and Kaylee you mentioned that ... You know, we're talking a little more about sales and maybe do you normally do, and I understand that, but your s- your marketing success is tied to sales.

Mm-hmm [affirmative].

So if you are, 'cause if they don't close the deal, or if they ruin your brand, you're the one to playing cleanup. Management comes to you and says, "I gave you a million dollars, I got no ROI on it." And you're gonna say, "But, but sales," and most organizations are like, "No, the sales guys are golden, we can't touch them. Because they're the golden goose, we can't can't touch them." Marketers you need to own the whole experience. You need to hold sales reps accountable, sales leadership accountable, and say, "I spent, uh, $500 on making this lead for you. It's qualified based on our SLA." Now, and this is why you need an SLA. "You need to go and not make these mistakes, instead do this, and make sure you do it right." So marketers step up, take on the big, bad beast of sales, hold 'em accountable because, dammit, it's worth it.

[laugh]. The last question. Last question. I realized we're at like top of hour and I was like, "Oh, we'll never get to the top of the hour," well, we're here. Um, my last question I always like to ask people is, who's another marketer in the space that you're following and find value from, that people listening should also go follow, listen to their podcast, read their book, whatever it is?

Easy. Sangram Vajre. All right. Co-founder of Terminus, he's their sales, uh, CMO, so he's the company of Evangelist now. Sangram just wrote a book called MOVE, M-O-V-E, and he's a co-author, and why this matters to you marketers is because, the whole book is a framework around go-to market. And he actually creates a recipe for what you need to do based on where you are in your company maturity. And it's literally step by step by step, do this, this, this, and this. It's stuff you marketers know, intrinsically, but when you try to convey it to your leadership and say, "We're not doing it right, we need to do this, we need to do that," and they all look at you with blank eyes, buy the book, give it to them, read it, and then say, "And we're gonna call a posse party together and we're gonna go over it and figure out what our go-to marketing strategies and why we're not getting the traction we want." Sangram Vajre is my recommendation.

Beautiful. I love it. Okay. Cool. Well, thank you, thank you so much for coming on-

Mm-hmm [affirmative].

... and just bringing so much energy to the podcast. I have enjoyed it so much. If other people listening need to follow you, obviously LinkedIn, but you also have two podcasts that you somehow have not mentioned, right?

Yes. I do. I just got off the recording in one to join this one.


Uh, so we have, uh, the one, the one I just got off is called, The Drive, and every single week we recap all the news that happened that week. Whether it w-was mergers, acquisitions, fundings, hirings, firing, gossip, rumor, innuendo. It's wonderful. Uh, and the other one I've been doing for forever is called, INSIDE Inside Sales, which is targeting at sor- sales reps. And it just teaches them how to be better sales reps. We have incredible guest list on the INSIDE Insides Sales show. Amazing.

Yeah. I love the name and I just feel like I couldn't have, I couldn't even say that you were a podcast host because I knew I was gonna be like, committed to saying it in your radio voice. And I just couldn't. [laugh]. I just couldn't commit.

[laughs]. I love it. Thank you so much. You're the best.

Um, yeah. No, this has been so much fun. I feel like everybody can take tons of actionable things away from today's conversation. So thank you for joining us and taking the time. Um, for anybody that's listening, I'll leave all the details and all the things that Darryl's talked about today in the show notes. If you wanna link to stuff and find, um, resources or download that book and read it, um, all of those things in the show notes for you. And we'll see you next time.

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About DGC
Demand Gen Chat is a Chili Piper podcast hosted by Tara Robertson. Join us as we sit down with B2B marketing leaders to hear about the latest tactics and campaigns that are driving pipeline and revenue.
If you’re looking for tactical ways to improve your marketing, this podcast is for you!
About Mastersaas live
MasterSaaS Live is the interview series that seeks to answer the question: What does it take to be a badass CMO? For our host Alina Vandenberghe, Co-CEO and Co-Founder of Chili Piper, this question is personal. A CPO-turned-CMO, Alina is on a journey to become a badass CMO — and is building in public as she goes. If you're a current or aspiring marketing leader, this is your only chance to learn from top marketing leaders, innovators, and big thinkers about marketing in 2023 — from CRO to brand to music and so much more.
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