The Power of Storytelling in Business Communication ft. Doug Landis | Revenue Reimagined Ep. 052

Doug Landis, CEO of DL Advisory, joins the podcast to unpack the critical role of storytelling in B2B sales, marketing, and leadership. Drawing on his unique background as a professionally trained actor and his extensive experience at tech giants like Box and Salesforce, Landis reveals why relying on "speeds and feeds" completely fails to resonate with modern buyers. He emphasizes that humans ultimately buy from people they like and trust, and stories are the most effective vehicle for building that essential empathy and connection. The conversation dives deep into how companies repeatedly misalign their narratives. Founders and sellers frequently focus on what their product does rather than why it matters to the specific human beings using it. Landis challenges organizations to source their best stories from Customer Success—the team closest to the real-world impact—and to construct a comprehensive "story library" that avoids treating giant corporations as "characters." Finally, Landis touches on modern leadership, highlighting the pitfalls of control-freak management and the necessity of vulnerability. He stresses that true leaders surround themselves with smarter people, openly admit their shortcomings, and leverage storytelling to guide their teams through friction and change management successfully.

Discussed in this episode

• How Doug's early acting training taught him the mechanics of eliciting positive emotional responses from an audience.
• Why speaking in bullets, speeds, and feeds is an inherently self-centered approach that alienates prospects.
• The origin of the "Chief Storyteller" role at Box, built to unify a fragmented and feature-heavy sales narrative.
• Why founders and sellers must stop treating companies as characters and instead focus on the real people affected by the problem.
• How product adoption and change management are the true indicators of ROI in modern SaaS environments.
• Why customer success teams should be the primary source for building a company's story library.
• The necessity for every organization to curate a "story library" mapped to different buyer personas and sales stages.
• How leadership maturity transitions from being an individual-contributor control freak to a vulnerable, people-focused guide.

Episode highlights

1. 0:00 — Introduction to Doug Landis
2. 3:15 — Doug's childhood acting roots
3. 6:45 — Transitioning to tech at Salesforce
4. 9:30 — Creating the Chief Storyteller role
5. 13:20 — Why founders focus on features
6. 16:50 — Storytelling for change management
7. 20:10 — Sourcing stories from CS
8. 24:00 — Building character-driven context
9. 27:45 — Building a company story library
10. 31:30 — Evolving as a sales leader
11. 36:20 — The lonely reality of leadership
12. 40:40 — Rapid fire questions

Key takeaways

• Build empathy and connection by telling stories about real people, not company logos.
• Source your most powerful customer impact stories directly from the Customer Success team.
• Adoption equals ROI; use storytelling to help buyers navigate internal change management.
• Establish a shared story library tailored to specific buyer personas and sales stages.
• Great leadership requires vulnerability, transparency, and a deeply rooted 'give a shit' factor.

Transcript

If I can, if I'm going to help you feel that and empathize with where you are based on what I've learned from other customers like you, then guess what, you're going to feel more safe and comfortable. With the coffee in hand, welcome back to another episode of the Revenue Reimagined podcast. We have with us today a name that is synonymous with the world of startups, um, more so with the art of storytelling. He's been called a sales professional wrapped in a marketer's body.

With a super deep understanding of customer advocacy. He's the current CEO of DL Advisory, an early stage storytelling, narrative building and go-to-market consultancy. But before that, Doug was the growth partner to Emergence Capital, which is an early stage B2B venture firm, where he was instrumental in the growth of some small companies you might have heard of like, I don't know, Zoom, Bill.com, Salesloft, Chorus, Ironclad, the list goes on.

Um, and prior to that, Doug spent some time selling, building and scaling at some other small companies. You know, Box, Salesforce, Oracle, Google. So wealth of experience, the master storyteller himself. Doug, welcome to the show, man.

Thank you. That was one hell of an intro, man. I got I got goosebumps, man. I was like, shit, I've done a lot.

Also means I'm old. You like that? Sometimes I like, I gotta bring Adam around to like introduce me to places. He doesn't give me that nice of an introduction, but See that that was that was this this is Dale, he's here.

And it's funny, pretty audience, you know, we were just reminiscing. Doug and I go back probably 10, 12 years just in the circle of the sales community. It's the first time we met in person, or E E person, so, um, Right. It's been awesome.

Um, but reminiscing is kind of fun. But, um, let's jump a bit into it. So, one of the big things is storytelling. Like you're huge in the storytelling, and what we find a lot with our founders is they don't do a really good job of giving their origin story.

How that origin story evolves and that emotional connection. So, I'm curious as you built out your advisory services, what was the origin story that you started with, and what can you give the audience from, uh, how to generate and build their own origin story? Uh, that's a good that's a good question, Dale. I I appreciate that one.

Right out of the gate, you know, first thing in the morning, got the coffee in hand, and you're like, So, let's get after it. Can we talk about your childhood trauma? Um, So, um, I what a lot of people don't know is I'm actually a professionally trained actor. I started acting when I was five years old.

Um, I went to yeah, it was it was just like the theater, being on stage, getting into character. One of the my first roles I ever, I ever got as a as a child actor was, uh, Raggedy Andy in, uh, Raggedy Ann and Andy at a performance. Um, and there was a there was a there was a creative freedom of expression in and that art form. And as I got older, I it's interesting, as reality TV shows kicked off, uh, I actually had some friends who were happening to be working at at CBS and a number of networks, because I grew up in the Bay Area, and they're like, hey, these reality TV shows, you should check 'em out, and you should audition.

And I did. And and I learned a couple things. One, I landed on four different shows, maybe five, I don't know. We can talk more about that later.

But but what I what I what I learned was, um, I I like the this this art form of communication was really, really interesting and powerful, and the camera and I kind of got along. And, um, so there was this this connection of like, okay, so how do I communicate to an audience, even right now, as I'm looking at a tiny little camera, how do I articulate and communicate to an audience that actually does the one most important thing that we're all trying to do when we're communicating, is is that it's elicit a positive response, right? And so, um, I I learned this, and I developed this as I was young and kind of up into my professional life. And, um, when I came back to San Francisco after, I think it was I went to University of Oregon, then went to Chicago, Denver and Chicago, and anyway, I came back and I was like, oh, cool, Jean Shelton's Actors Lab acting community in San Francisco, she's one of the creators of of, um, the kind of the two core forms of of acting development.

And, uh, and I went to school there, and I graduated from it. I realized like, wow, this is this is so fun. I don't want to move to LA and go be an actor. What I want to do is I want to incorporate this into the professional world.

Because growing up in Palo Alto, I got to see companies like HP and Sun, and and even the likes of Google and Facebook and and Twitter really kind of blow up. And, um, what I realized is like, this this this communi this this vehicle of communicating, uh, incorporating story form in communicating is so powerful. And yet when we are at work, we speak in bullets and fragments, and we talk speeds and feeds. We talk a bunch of BS.

And and, you know what, I so what I realized, and then I had the good fortune of working at this little company called Salesforce in the early days. And, you know, one of the greatest marketing, I would argue one of the greatest marketing organizations, sales and marketing organizations, ever to be created. It's got the sales in its title, it's kind of cool. And what I learned was, there in particular, was this whole notion of like, well, look, the reason why we speak in speeds and feeds and bullets and and fractured statements is because we're talking about ourselves.

Right. And the only way to actually really get customers to showcase this customer-centricity and customer love is to speak about them. Well, the easiest way to speak about them is to tell their story. Like, oh, okay, cool.

So like, it all kind of fit and, um, and and and and played well together. And it was interesting, so I left Salesforce, and I went to Box. I went to go work for Aaron Levy, and he's a pretty phenomenal, um, orator. Um, he's so effing smart.

And and it was really interesting, and there's a there's a there's a pivotal moment in in my career where we were about we're we're trending into about a hundred million dollars, and we just hired this new CRO. Um, this about this is probably about 10, 12 years ago. Um, dashing young man who was like there to take us public, and um, of course, anytime you hire a new sales leader, sales leader wants to walk around the floor and meet all the sales team. And so we do, and I'm introducing him to all the players and, you know, all the people that he needs to know.

And, um, he asks everybody, he's like, okay, well, how do you how do you talk about Box? to to like, 25 different people. We got 25 different answers. Not uncommon.

Not uncommon. But what was what was common was there was there was no consistency at the core of who we say we are and what we do. There was no value in it. It was all me, me, me, me, me, look at us.

And and unfortunately, when when when we're thrown more products, what happens is we default back to our comfort zone. So at in Box's case, it's like, oh, we're in cloud storage. And and of course, if Aaron ever heard anybody say that, he'd fire them on the spot. I mean, not really, but theoretically.

Uh, and so we I realized what I'm like, we have a we have a problem. We don't know how to pull and infuse our customer language and our customer stories, and our customer, um, experiences into our the way in which we talk about who we are and what we do. So, I've been at Box about, I don't know, maybe five years, and I went to Aaron and I said, hey, um, I want to create a new job for myself. And he's like, what?

I was like, I want to, uh, I'm I'm gonna create a job for myself. It's it's called the chief storyteller, and I am going to reorient how we talk about who we are. And then I'm gonna train everybody on that, because the reality is, is there's one thing to create the stories, right? Which just takes some work, marketing.

I'm looking at you, marketers, you. Like, none of this problem solution, ROI. That's, oh, such BS. Um, so marketers need to figure out how to create these stories.

And then sellers actually need to know how to become a better storyteller, how to how to look for the signals to get into a story, and how to look for the signals to get out of a story, because I don't want you to be telling stories 24/7, because that's just a weird form of communicating. But but you need to understand the mechanics of it. So, that's how it happened. Cool.

I love it. Oh, that was a really long story. I apologize. But but it but it's so true, right?

We as sellers, and we we work with typically early stage, call it A to C stage startups, some preseed. Um, and I actually I I I have a post-it here on my desk that ties similar to what you were saying, Doug, and it's I ask every founder the same question. What's the number one problem your product solves for your prospects or your customers? And most founders that we speak with don't tell a great story.

They don't talk from the buyer's perspective. They talk about it's a feature dump of, well, my product does this and we do this and we do this, this, this, this and this. Yep. And I'm guessing you saw a shit ton of that when you were at Emergence, probably now, and even back in Box, uh, and Salesforce.

Yeah, so it was interesting, um, you're you're totally right, and and this is the look, founders aren't the only ones that suck at telling stories, by the way. Sales people also suck at telling stories, just to. By the way, so do marketers. I'm gonna keep picking on marketers today.

I don't know why. I yeah, I like, I still have my coffee. I'm just like, we're gonna duke it out, marketers. Um, because you can make sellers lives a hell of a lot easier if you actually help them with the things that they need.

Um, yeah, yeah, I'm going at you, marketers, I'm looking at you. But and we'll get there, and I'll tell you what you need to do for them. But so, back to your question about so, like these origin stories, these founders, well, here's the problem. On on the one hand, you have a lot of I I feel like you have a lot of founders that are like, they're hammers looking for nails.

They're really effing smart. They know how to build product. They they they saw a problem in their company, and they experienced it like, let's go solve for that and let's go build a company out of it. And you're like, all right, dude, that's like a feature.

That's not a real company. Um, and so, and so you're kind of like, well, what what's your connection to this problem? Oh, I saw our sales team struggling with it, so I decided to go build it. It's like, all right, that's interesting.

But do you really get it? Do you really understand why it's a problem? And I and this kind of goes back to the, you know, the like the ethos of when you're working with early stage founders that are product or engineering-led, and even sellers, because we train them to do this. We focus too much on the what we do and how we do it.

And we don't focus enough on the why. Mhm. Like, look, as investors, we're making bets on people. We're not making bets on your technology.

The truth is, is we're betting on you to out-technology everybody else, out-execute everybody else. And in order to do that, you actually truly need to understand the problem from your buyer or your your even the user's perspective, and to viscerally get it, and to understand what it is doing to them in their lives personally. It's interesting, I came up with a um an example that I came up with at Box, and this is tripping people out. They're like, who's Box?

What do you doing? I'm like, oh, we're in the business of saving lives. Everyone's like, what the what? You aren't you a cloud content storage?

I'm like, oh no, no. We are in the business of saving lives. And then I would explain the situation of a doctor sitting in an ER, in the ER, dealing with a patient who's on a multitude of medications and having all sorts of complications, and has to go all the way down the hall to log into an old archaic system to try and look up these symptoms, to try to determine what they recommend. It's like, well, what if you just had an iPad, and he's like, this is the issue, boom, done.

Oh, cool. This is what I need to know. And this is what we do. And the difference between the 60 seconds walking down the hall and logging in, and doing this right now, could save somebody's life.

Right? And so it's like, it's like, it's it's orienting, and and ultimately, if you really think about it, like the easiest way to become a better storyteller is just to like spend a lot of time with your customers, like get in their seat, sit in their seat, get in their shoes. Think about what what what they're giving up in their life to try and get their actual job done, right? Um, and you know, it it it it it matters.

And here's the other thing, too, for founders, since you all work with early founders, we all need a purpose, and especially Gen Z right now. We need a purpose for going into work. I need a purpose for working for you and working with this company and trying to solve this problem. If you don't give me a good purpose behind it, which is more of the why, why do we do this?

Well then it's it's kind of hard to get behind it. And I don't feel like I'm just kind of selling widgets. Well, it drives back into earlier when we're having a conversation on leadership, right? And so, how do leaders become better leaders, and when they talk to their the organization, it's about the why.

Like we can say, make these calls, have a storytelling process, etc, etc. But why are you doing that? Because now you can be relatable to customers. And a lot of times, when we'll train sales reps, I like to train from objections versus feature functionality.

Like, you'll hear about our product three million times between now and the end of the month. But you won't hear, forget about price sensitivity, that kind of bullshit excuse. Like, what are the real objections? Well, I'm, you know, you I'm worried that you guys won't be able to fit into our, you know, infosec infrastructure.

Okay, that's a real objection that we now need to solve for, because that's a pain point that the customer is going to solve on. I just find we don't deal with objections the right way. Which so to me, that's a that's a great entry point. And again, you know, when it comes to storytelling, I don't want you to talk in story form 24/7, because that's just weird.

We don't do that in our personal lives. Uh, right? So, like, you got to know when to get into and out of story. Someone gives you an objection, it's a great opportunity to get to tell a story, to like reorient like, okay, I like, totally recognize because I've heard it before.

In fact, you know, I was talking to Steve. And, you know, this is what he shared with me, uh, you know, about this, how it fits in the infosec, uh, ecosystem. You know, one of the one of the most important objections that I think nobody spends enough time on, the biggest fundamental issue that we all face in the world of SAS, is change and change management. We just think our product is so easy, and it's so powerful, and it's so simple, and it hooks into everything.

And everyone's just gonna use it. It's like, no. And I've been saying this phrase for, I don't know, probably feels like two decades now, but adoption is ROI. Adoption equals ROI.

It's not the new ROI anymore, because I've been saying it for so damn long, but it's it really truly is. And so, if people aren't using your product in a way that that you think is is is likely to deliver the most value, then you're missing the big important salient point here, which is all about change and change management. And and again, you can tell an amazing story about how how you can drive change management into an organization, um, pretty quickly and seamlessly, but you got to know it. You got to understand it from a customer's perspective.

So, look, there's the reality is, is there's so many opportunities to incorporate story form and narrative form into your company and into how you communicate, not just internally, but also externally. People just need to be more consciously aware of it. People buy from people. That's why companies who invest in meaningful connections win.

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If you're looking for a proven way to win and retain more customers, visit Sendoso.com. Where where does where is that responsibility lie, Doug? Like, I and I love how you keep calling out marketing.

But, you know, is it marketing? Is it sales? Is it getting everyone around the table? Like, how do we build that story?

Yes. Yeah, totally. Well, it's it's well, I mean, I'd say first of all, it starts at the top. Like, you know, look, great great leaders are usually great storytellers.

They just are. They're great communicators. And they understand because they understand how to communicate from different perspectives and points of view. Right?

So, I they and oftentimes, great leaders speak from the point of view of their customers, it's because they spend a ton of time with their customers. All those CEOs out there that are afraid to talk to their customers, I think it's largely because they don't know what to ask or what to say or how to have those conversations, which is unfortunate. Need to go spend some time getting comfortable with that. But because all the great leaders that I know are super, super entrenched with their customers.

And so they can pull, they just have a natural arsenal of stories to tell because they've been spending all this time with customers. And our job is to help, you know, you, Adam and Dale, feel safe and comfortable and not alone in dealing with the problem that you're dealing with. And so, if I can, if I'm gonna help you feel that and empathize with where you are, based on what I've learned from other customers like you, then guess what, you're gonna feel more safe and comfortable. So, it starts at the top, number one.

So, your leaders have to get better at telling a story instead of like dictation. By the way, you can still use facts and stats and all that stuff, just lead with stories because it's a better form of connecting and communication and and empathy demonstration. Um, but when it comes to actually creating the stories, I'm gonna actually lean on customer success first. And here's why?

Because they're closer to the customers. They know, in the in your customer's words, the true value that you deliver, and where in their jobs, and in your customer's life, where does that value impact them? To what degree? Right?

I'm not talking about like, saving time, reducing risk. That's all great. Yeah, CEO, CFOs care. I get it.

That matters. But I also care about like, hey, can I give Sue, this mid-level marketing manager who works at Coca-Cola, can I give her her Sundays back? Mhm. Can I give her freedom to actually be able to go to her kids' softball games?

I don't know. I want to know where we hit people, you know, in in real life, not so much just at the bottom line or top line, however you want to think about it. So, I'm gonna look to customer success. I want some of that language.

I want some of that, I want some of that juice that they get from talking to customers. And I want that fed back to both product, and I want that fed back to marketing. Now, marketers, I'll pick on you here for a minute. Because y'all should be good at this.

We're talking about this offline, um, before we started, so I'm just gonna say it now. We do spend all this time training sellers and SDRs and customer success folks and resell, doing renewals and upsales and all that stuff. Who how do we train marketers? Where's their training?

Where's their development? Um, it's funny, I do all these storytelling workshops uh all all around the world, and it's it and and and and most of the time it's for sellers, and I'm like, uh uh uh uh I want all customer success, and I want all marketing there. I want anybody that is customer-facing, because hey, marketers, your job is to help us sellers figure out the core components of the stories we need to be able to tell, right? So, as marketers, here's the here's the key, marketers.

Your customers are not characters. Cisco's not a character, Coca-Cola's not a character, Home Depot's not a character. I don't give a shit about those logos. I want to know the people in those companies whose lives you're changing.

Right? Open Table Joe. I was just at a at a company in Atlanta yesterday, and we were talking about Open Table Joe and and his role. And it wasn't like, so we know we weren't talking about Open Table.

I was like, I don't care about Open Table. I care about Joe. And what was Joe dealing with? And what was Joe's life before this, you know, before before we stepped in and helped out?

Right? Because there's a couple things that are really critical in storytelling. One, we need characters, right? Two, we also need context.

Right? So, most stories are missing context. When I when you asked me, Dale, about like, what's my origin story? Um, I mean, I went all the way back, right?

I started acting when? When I was five years old. Five or six. Right, right.

So, I gave you context. Now, you don't know how necessarily old I am, but like, oh, a long time ago. But now you have some context because I had a starting point. I set the stage for for this journey I was going to take you on.

Right? And that's often what's missing is that context. So, that context is either from what was to what is, or what is or to what could be. Yep.

Right? And so, when I have these things, when I have these elements, it makes it easier for me to be able to tell the story. The other thing that's really missing often times in our stories, and this is an exercise that I do with everybody, so, free, you know, here's a free tip for everybody. Go through all of your customer stories.

Ask all of your sales people, what's the point of this story? Yep. What's the point of it? In in a world curious how like, what stories the sales people are telling, do they really align to what ends up as a result?

Like, if if customer success is getting results on this, yeah. Are we telling these stories or are we telling some completely different value story? Well, most often, we're telling a different story, because that that information from customer success isn't usually fed back, right? And so, it's that feedback loop that's usually broken, and it's missing.

And so customer success is telling one story, and sales is trying to sell telling another, because sales thinks, well, we're on the front end of the process, and customer success is on the back end of the process. And so, you know, maybe our story should be different. The truth is, yeah, look, the reality is, is every company needs a story library. And you need story time in your company.

Like, you literally in your in your team meetings, you need story time, and everyone needs to get up and tell a story. And then you're going to evaluate whether or not that was a real story or not, or whether or not it was just a list of a statement of facts or just a sequence of events, because often times, people just don't understand the difference. Yeah, it's it's a bedtime story, but let's do it at work, right? So we can start to so we can start to build this library so that we know what stories to use when, because I I guarantee the companies that you work with, they likely have two or three stories that they all tell over and over and over and over again.

And they're not necessarily going to be that relevant to every audience that they speak to. I mean, when I'm talking about a story library, I want a story library for every one of your buyer personas across every stage in the sales process. Because you should be telling stories even at the commercial stage when you're negotiating. And you should be telling stories when during the handoff, when you're giving it to customer success.

It's not just in the front to like tell you my origin story. So So that's super interesting. Sorry, Dale. That that's super interesting to me.

And I think a lot of people don't think that way, right? Like, we talk about origin story a lot, and we talk about the importance of a a proper handoff and making sure that, you know, we're setting the stage. But I don't think I've ever heard anyone say it in the phrase of like, use storytelling throughout, right? When we do that handoff, why is this important to do it this way?

And what do we see? And what is it get you? And tying it all together. So, super interesting.

Sorry, Dale, I stepped on you, man. Well, but Adam, just think about this for a second. Buyers, people buy from what, people we what? Like.

And? Trust. Yes. How do we build that likability and that trust?

Not from spewing off a whole bunch of facts and Yeah, not not not feature-dumping, it's Yeah, and telling you how it works. Relatability. Storytelling. Relatability.

Um, Yep. Right? And so, why wouldn't you? I think part of the challenge is people one don't have the stories to tell, two don't have the skills to actually tell the stories, and three don't know when to actually tell the story for which which, you know, persona and which stage.

Like, what story do you tell? Or they just don't practice. Or they just don't practice. And that's and that's the other thing.

They also don't practice, because it takes work. Like I I I literally in a in a session yesterday, um, you know, and I I I like to put people on the spot. And and a great, you know, a great exercise is just like, okay, so, Dale, why why why Revenue Why Why partner with Adam? that's a long story.

Why Revenue? Yeah, Why partner with Adam? Why? I mean, cuz you you wanted the number to go up and to the right.

That's the story. But but here's the thing, like, both of you need to have your own why story. Why did why did you start Revenue Reimagined? Why work with each other?

Why does this matter? Because if you don't have your own personal why story, and this is why you work at any company, um, it's hard for people to connect because I want to know that. As a buyer, I want to know that. Like, okay, what do you, why did you go there out of, you know, like all the things that you could do, why go do this?

Because now I'm getting to know you. And as I get to know you, I'm starting to build a connection. And in every interaction that we have with anyone, in particular, in this world, our job is to do three things. Build a connection, demonstrate some level of empathy and credibility.

100%. I love that. Our stories are very long, so I just I just Our stories not many bullet points. Um, you know, going back to leadership a little bit, Doug, um, you've gone over, like, you're you're you've gone through like Oracle, Salesforce as some of the young age, you know, Box and brought to a hundred million.

How has your leadership evolved over time through all these stages of your career? Ooh, wow. I mean, that's like, we're we're back to like childhood trauma conversation here, um, Dale. That's what I I like I like to I like to put the dagger in.

I don't know I don't know if it's a dagger. I think it's more like, look, as we mature, we recognize that there's like, there's a lot of different ways to, you know, to get things done. Um, I feel like, and in my younger years, my biggest kind of leadership gap was like, I was just too much of a control freak. And it's like, you know, typical frontline sales leader, where you're like, okay, let me take it over.

You know, there's an important call. I need to get the deal done in order to actually hit my number. Uh, you know, you can kind of feel the conversation's not really going where it needs to go, and it's like, okay. So, Adam, let me just kind of summarize where we are, and what, you know, I and and and I want to get into like, these two kind of hurdles that I think are really keeping us from moving forward, right?

Next thing, I know, it's reps are like, okay, cool, you go take it. Um, and I think, you know, and I think often times, I have a lot of energy, and it's like, it sometimes I used to think that it was like, you know what, it's just easier if I do it. Yep. Um, and look, I still struggle with that, because I still like, oh, I got it.

I got it. I can do, I'm Superman. I can do 18 different things. Um, but I now, I feel like, to me, leadership is much more a a people responsibility role, and that like you really need to to understand your people from a from a perspective of like, of who they are as human beings, and what really matters to them, and what's going on in their world, and like, like really have a very, very high, you know, my my boy JB and I talk about this all the time, but like, a really, really high give a shit factor, and your actions need to be in line with your words.

Um, and and I think the other thing, too, is like, and of course, my my good friend Todd is like, all about transparency. Like, the more we acknowledge as leaders, you know, our our shortcomings, it doesn't mean you are, you know, people are gonna question your ability to actually lead this company and tape take it public, or whatever. It's like, no, you're human. We're all human.

And we all have our strengths and weaknesses. And my job as a leader is to kind of fill those those gaps that I have with people who I would argue are way smarter and way better than me. Um, I'm not going to be perfect. I'm going to make mistakes.

And we need to train leaders just like you were talking about training marketing, like, we need to train leaders and give them the ability to have some transparency, some accountability, some self-awareness. And I think, you know, I think I think those are all the things that I've seen as I've grown through a leadership is the insecurity you have as a young leader into the ability to know you're going to get more done if you circle yourself with the with people that are smarter than you and do things in a different way. And I think, um, we need as a as a community of leaders to do a better job of helping train future leaders because that's the only way a lot of these companies are going to grow properly. I agree.

But the you know, the other thing is, too, I think I think unfortunately, we we live in a society of we're we're just more more fear-oriented and fear-driven, right? And so it's like, especially if you're a, you know, look, the two loneliest jobs in a company are the CEO and head of sales. Like, Yep. Straight straight up.

Um, you know, marketers, no offense, but y'all can hide what you do, and, you know, and and in numbers. Look at all these leads. Got the Glen Garry leads and sales people. It's pretty straightforward, like, um, sales people are like, you either hit your number, you don't.

You know, and if you don't, it's your fault, you're out, right? And it's like, oh, well, that's interesting. Well, let's see, the product doesn't work. We can't get anybody implemented.

Nobody knows about us out in the market. Um, you know, I've been asking for new product capabilities for two years, not getting any of that. But sure, I suck as a sales leader, so go ahead and fire me. You know, it's like, you know, we know going into this that like, this is what we're dealing with.

And and I think, you know, I think it's hard for people to have really honest conversations because, guess what, it starts at the very top. Investors, like, you have I have a fiduciary responsibility. If I've invested in your business to show that this is a good investment, and I care about two things, doing deals and increasing valuation. And if you're not increasing valuation, then we've got to make some changes here.

If if we're not actually hitting, you know, escape velocity here, we've got to potentially make some changes. Unfortunately, if we're missing our number, number one change is got to bring in a new sales leader. I can't tell you how many times I'm like, I'm trying to I would be talking like board members off the ledge, like, okay, can we not freak out right now and go fire this person, and can we kind of focus on some of the other things that are not going right in the business and think about this holistically, and think about the implications like, if you use them as a whatever, what what do they call that? Like, if you use them as a Yeah, scapegoat or like, oh, we're gonna send a message, it's like, oh, awesome.

They're going to use Yeah. The example. The example. Yeah.

You gotta fire the sales leader today. Yeah, right. Right now. Yeah, like, um, you know, these early founders, if they're if it's their first time, they don't know how to do this.

And they're getting pressure from their board and their investors and, you know, they're lonely. They're like, who do I talk to? I can't go talk to my team because they're going to maybe start to lose some confidence in me. I can't go talk to my investors because they're going to likely lose some confidence in me.

So, I need to go talk to other CEOs who maybe are in the middle of doing this, maybe not. And maybe the uh, you know, so you gotta be there's a level of vulnerability and transparency that you've got to get comfortable with there as as a leader in situation. And I think that's why we I think that's why we actually have a really good um, play in the market because we actually play that like advisory role to help CEOs, like, how do I have this conversation with somebody that can help me work through it instead of being in my own echo chamber? Like, I know I I I'm a victim of source.

When I was the CRO, head of sales, like I always tried to play the political game because, obviously, you don't want to get fired, you're trying to play inside the lines. But like, as the position that Adam and I are in, like we don't have to, like we tell you the truth. Whether you like it or not, that's gonna be up to you. Like we we've seen this script.

We know the story. The ending doesn't bode well for you. You know, you know the challenge I think we have though in our advisory capacities, it's like what what I often struggle with is like, I can tell you a hundred times, but you have to you have to choose to listen to go, you know, follow the advice. I've seen this movie a thousand times.

I know what's likely going to happen. Likely, I don't know for sure. Um, and I'm gonna tell you all these things and then it's your job to go to go do something about it. And, um, it's that that again, kind of goes back to that leadership.

It's like, that gets frustrating, it's like, oh my gosh, don't do that, don't do that, don't do that. Oh, you did it. Okay. Well, that's not gonna bode well.

Like, hey, look, you know, you're paying me to tell you the truth, I told you the truth, you didn't listen. So, okay, that's that's kind of on you. Um, but I want to see everyone successful, and I don't want to see it's like a parent. Like, I don't want to see you make the same mistakes that I saw the older brother make, right?

Because, you know, I know if you jump off that, you know, I know if you, you know, go off that BMX ramp, ah! You got to break your damn arm. Greater than 50% chance something bad's gonna happen. I'm just saying.

I've seen this before. Oh, I know you're special. But okay, do it. Everyone's a snowflake, Doug.

Everyone. Yeah, that's true. It's true. Damn, we covered a lot.

I think, you know, it's it's so funny to me. And and we did cover a lot, and I I wish we had more time because I could go for another 30 minutes. But when we talk to founders and sales team, and what you're saying about like that sales leader being fired, like Dale and I have both been in that seat, on both sides of that seat, for the record. Um, and it's often the wrong gut decision to make.

Like, listen, there are times you absolutely need to let a sales leader go. Make no mistake about it. Um, but generally speaking, the problem, and we see this all the time, is, well, the sales leader was hired 34 days ago, and you expected them to miraculously fix everything that the previous sales leader you fired in 34 days, and, you know, triple the revenue, and it just doesn't work that way. That's the worst.

That's the worst. You're like, oh, wait, so you're hiring someone to fix all the shit that you couldn't fix the first time around, and you're only giving them three months. Right. Why do sales leaders only get three months to ramp?

I don't know. Like, we hire an enterprise AE and we give him 12 months to ramp. Well, likelihood is like six nowadays. But okay, let's give him let's just let's let's just do nine.

Let's let's land on nine. We get a sales leader, you only get three months. That's it. Like, if you haven't fixed everything and we're not like starting to show progress.

It's like, dude, in three months, I'm just now figuring out like, how the hell I get my marketing counterpart and I do agree on a number that is not, quote unquote, leads. 100%. That's all BS. Okay, Doug, let's let's let's wrap this up a little bit.

You ready for some rapid fire and we'll uh we'll get you running. Let's do it. Let's do it. All right, first question.

Here's the rules. You get 10 words or less. Otherwise, there's this miraculous gong that comes out through uh through River City. It's the special platform we have.

Um, and it goes, and it tells you to be quiet. Early bird or night owl? Early bird. If you weren't in tech and you couldn't act, what other profession would you be in?

Golfer. Nice. No hesitation. What's your What's your favorite What's your handy cap?

Uh, I'm currently an eight. Woo! Wow. Trying to get to trying to get to scratch.

Only playing for four years. Wow. What's your favorite guilty pleasure snack? Um, Chips and salsa.

Okay. No guac? Just salsa. No, just chips and salsa.

Yeah, okay, cool. Don't complicate the shit, Dale. Yeah, I'm I'm simple. Besides yourself, who's the best storyteller you know?

Ooh. I have two. I'm also biased because I love them both. They're very dear friends.

Um, uh, yeah, I probably have three, because we this is how we communicate. This is like we we talk in this form. So, uh, Jen Allen, John Burrells and Amy Valis. And the like, the four of us just sit around and tell stories.

Um, we don't BS each other. Cool. I love it. Doug, you've worked with a lot of startups.

Um, both as your as yourself working there, and also with Emergence. When you look at the state of startups today, what's one word to describe the state of the state of the startup ecosystem? Struggling. Yep.

Yeah. Like it. Yeah. Last one to wrap us up.

Dream vacation destination. Ooh. Scotland. Scotland.

Nice. You got to go, yeah, you got to go play the old course. Yeah, played the old course. Knew that was coming.

Love love Scotland. I had the best Thai food of my life still to this day in some back alley in Edinburgh. I love it. I love it.

I love it. By the way, I I've been I've been to Scotland, and I love it. I went I went there for the art festival in August, and it's the craziest town on the planet in that month. Um, I just want to go there to play golf.

My first response actually was Greece, but I'm like, yeah, but I can't really play golf out there. Just hang out and look at pretty water. Doug, thank you so much for joining. Where can people learn more about your new advisory services?

How can they find you? How can they interact with you besides LinkedIn? We know LinkedIn. Yeah, yeah, yeah.

LinkedIn. Is funny, most out of most social media platforms, I probably spend more time there than anywhere else. Um, I'm old school like that. Um, but you can you can find me at uh dladvisory.

co, or douglandis.com, they both go to the same place. Um, yeah, just find me there. Cool, man.

Doug, thank you so much for joining. Awesome. This is awesome. Thanks guys.

This is really fun. Cheers.