In today’s post, we present The Cutting Edge, where the best sales leaders in SaaS share cuttingedge tactics and strategies. Doug Landis, Growth Partner at Emergence Capital shares his expertise on the art of business conversations and how your customers should inform your go-to-market messaging.


Doug Landis:  For me personally, right now, currently I am a growth partner at Emergence Capital. If you don’t know Emergence yet, just yesterday we announced we raised $950 million over the course of two funds. Good news. So we’re a B2B enterprise SaaS-focused early-stage venture firm.  We made a bet 16 years ago that all software was going to move to the cloud. That was a pretty good bet because we were first or early investors in Salesforce and Box and Yammer and Veeva and Zoom, SuccessFactors, and more.

Bryan Elsesser:   All very small names, all very small names.

Doug Landis:  We’ve picked properly. But at the end of the day, for me personally, I am a lifelong student in the profession of sales. I’m a sales professional wrapped up in a marketer’s body, I’m maniacally focused on all things go to market and I’m basically free go to market consulting for our portfolio companies. I was fortunate enough to be at Oracle way back in the day, making a hundred phone calls a day. And if we didn’t, you’re on the bottom of the list, you might get fired. I was early at Box, at Google, at Salesforce. So, I’ve had a fun run.

Bryan Elsesser:   And some of those brands people today would there’s a lot of sellers today would just absolutely kill to get into one of them. And you’ve been a part of so many. So, that’s really incredible. I mean, it’s funny, I know we said career story, you started with how things are not linear, but you said the word “story”, which let me say you something like how I met you, right? I saw you speak at Rainmaker in 2018 on the topic of story and how story can infiltrate sales and the power it has. So, I’m hoping at some point today, we can dive into that. But first and foremost…

Doug Landis: Absolutely.

Bryan Elsesser:  …the key question of today, Doug, what does a Cutting Edge sales team need to do to be seen as a trusted team today?

Doug Landis:  Man, I will tell you, and there are bazillion tactics out there that you can use, whether that’s strip lining from Sandler, upfront contract, whatever it may be. The one thing that I see most companies really struggle with today I’m going to throw a wrench in everybody’s kind of sales process as it stands today, because I hate the stage discovery. Forget about it being a stage. It is what you do in every single conversation that you have with a prospect from the time you identify them, because part of discovery is actually research, all the way to the time you hand them off to customer success, discovery is continuously happening no matter what, no matter how so, why the hell do we have it as a stage? Because when we have it as a stage, because what we do, we set ourselves up just to do a checklist of questions.

And as the buyer, it becomes an inquisition. And you wonder why 60% of all well-qualified deals end in no decision. You lose to the status quo, even when it’s qualified. Why? Because you are doing a discovery call and you’re doing a demo and your demos suck because there’s no narrative, you’re just showing features and capabilities.

But, that’s not actually what I want to highlight. What I want to highlight is, instead of getting focused on the discovery, I recommend two things. Number one, you need to have incredibly deep domain expertise in knowledge. What that means is you need to know the industry that you service and you serve and you support inside and out everything about the industry. Is it growing? Is it shrinking? Is it international? Is it not? Who are the key layers in the industry? Who are the market makers in the industry?

And then you need to know everything about the companies in that industry. So, if I’m targeting a specific vertical, and by the way, I would highly recommend, even if you have a geo territory, you start to verticalize even your geo territory, because context switching is hard. If I’m talking to somebody in oil and gas, and then I talk to a healthcare company in the next phone conversation, I am screwed, I’m all over the place. But, if I’m talking to somebody in oil and gas, I need to know everything about oil and gas. I need know everything about that industry. And why are gas prices going up right now? Pisses me off by the way, by the way they’re going up because more cars are back on the road because we’re all getting vaccinated bananas. But, if I was calling somebody in oil and gas, guess what I would do.

I’d be like, ‘so you guys are rolling into cash these days. Congratulations. Let’s talk about how you can spend that’. I mean, I’m kind of tongue and cheeking it, but at the end of the day, you got to have deep domain understanding and expertise.

And then from that, so what do you do with that? It’s like, great, you’re smarter about oil and gas, congratulations. You use that to build a hypothesis or a point of view about their business. You must enter every conversation with a point of view, a point of view about the business, about their business and about them. So Bryan, if I was calling on you and your oil and gas, I’m going to have a point of view about oil and gas in the industry and a point of view about your business. What I mean by that is instead of going into a discovery conversation, you’ve got a hunch.

It’s like, ‘Hey Bryan, listen, it looks like right now, things are turning around. I know things are really tough because nobody was driving’. And there were probably fears about the fact whether or not oil and gas was going to survive as a top two industry in the world. Now, all a sudden it feels like things have shifted, which is fantastic. I also recognize the fact that because of this shift, you now are in a position where you’re thinking more about transformation because you freed up some space and now you’ve got the room to actually go focus on how do we set ourselves up to be wildly successful next year.

Bryan Elsesser:   It seems like a great premise and basis for challenger. No?

Doug Landis:  I mean, it really is. I mean, yes, you can use that to set yourself up, to ask a challenging question or, I mean, literally, you can set yourself up to have asked really any question from that. But, the problem is, if you are entering into a discovery conversation with your list of questions, you’re not being present, you’re not being empathetical.

Doug Landis:  You’re not demonstrating real empathy. And at the end of the day, it feels like from the buyer’s perspective that you don’t get me. And so why do I want to have a conversation with you? If you think about Challenger; teach, tailor, take control, right? Well, guess what? None of that can happen unless you can demonstrate that you get me. And if you can demonstrate that you get me, then you can start to have a hunch about maybe what I’m focused on.

Look, every company is focused on one of three things as a strategic initiative, every company in the world, I don’t care if you’re a Mom Pop dry cleaner, you either grow in revenue, mitigating risk, or managing costs. And those are typically identified at the top level and they trickle their way down, all the way down to the individuals and the managers and the directors and the VPs that you’re calling on. So, when you know that, and if they’re focused on growing revenue, be like, ‘oh, I’ve got a hypothesis’ that you’re focused on growing revenue, I think I might be able to help you do that, by the way, there’s a kicker to all of this.

Doug Landis:  You, your voice as a salesperson, unfortunately, carries very little value because you’re in sales. And so how do you, if I were to say Bryan, I think there’s ways in which I could help you. You immediately, you’re going to be like, ‘that sounds like a sales pitch’, right? So, I want you to take the I out of the conversation,

Doug Landis:   And say, you know what, Bryan, I was doing a bunch of research, and the reality is you look and feel and sound very similar to Jeff, who’s the VP of Revenue over at Chevron. And I was just talking to him yesterday and some of the things that Jeff was sharing with me about what he’s struggling with right now, even though they’re hyper-focused on growing revenue and they’re growing like crazy is one, two, and three.

Doug Landis:  So, now I’m using what I’ve learned from other customers that I feel are pretty similar to you. And I’m sharing some of the things that I’ve learned with you, that’s aligned to my hypothesis. And then I could say, how does that resonate with you?

Bryan Elsesser:   I guess, like I have a question here, right? So, I’m an old Yellow Pages salesman from back in the day. Right?  It was an amazing upcoming in sales. But, one of the upbringing in sales, but one of the things that they taught us really early on was that, I remember my first manager said, “look, any industry that you’re going to go and talk to, you need to go and spend some time in an Excel sheet in brainstorm and research and think about life from their point of view before you can send a step foot in their business”.  it’s 10 years ago. Right? But, that being said, right? If it’s 10 years ago, but we’re saying buyers have changed, have they changed?

Doug Landis:   No. No. So, here’s the thing. Yes. They’ve changed because they have access just so much more information and yes, they’ve got more responsibility and yes, they’ve got more at their fingertips and yes, yes, yes. Buyers have changed, but guess what? They’re still human beings. And that hasn’t changed. And people buy from people and people buy from people they like, and people buy from people that they trust. And so how do you build trust? How do you build credibility in a conversation? I say, you know what, Bryan, you are so similar, or in my mind, I feel like you’re pretty similar to other people that I’ve spoken to that are just like you in a role in the same title, in similar companies, similar industries.

Bryan Elsesser:  Right.

Doug Landis:  Right. And, oh, by the way, because I know I’ve got this deep domain, I know by industry, by persona, what you most often struggle with. Because again, we’ve done all our homework and in sales reps, I’m not saying that this is up to you to do all this homework you should, but marketing needs to help you with all this insight knowledge and information, because, you’re going to freak out and be like, how do I spend all this time doing research? I need to have a life and I get it. You need there’s balance.

Bryan Elsesser: But I think there’s tracks of balances…

Doug Landis:  But it’s also on you to study. It’s also on you to study.

Bryan Elsesser:   But, it’s also checks and balances on the leadership as well. Right. Leadership needs to be involved in that conversation and it needs to be a full court press. It can’t be an accidental success. So, I think you’re a [crosstalk] 100% on that. Absolutely.

Doug Landis:  By the way Bryan, what you’re doing is you were demonstrating empathy. I mean, empathy was one of the number one most talked about topics in the world of COVID right. It hasn’t, it’s like, how do we demonstrate empathy now that we’re over zoom? Guess what, demonstrate you get me. How do you do that? Do your F’en homework.

Bryan Elsesser:  Well, I think it’s actually interesting you bring up the word empathy. We had, it was probably the number one buzzed sales word at the start of COVID. Right? Like everyone was like, “oh, you got to show empathy”. “You got to show empathy”. “You got to show empathy”. I don’t think I ever really knew what that word meant, because all I saw was sympathy. Right. And that’s a very different word. It’s a very different word.

Doug Landis: High five, a 100%. The problem is we were talking about empathy, but no one was teaching people how to demonstrate empathy.

Bryan Elsesser: Right.

Doug Landis:  How do you demonstrate empathy in a conversation when, by the way your sales process says, ‘I’m in discovery stage right now. Okay. Bryan. So, how are you feeling in COVID? Okay, cool’. So, tell me what software are you using for? What are you doing? How do you solve for it? But, they’re like, oh my gosh, shoot me in my head.

Bryan Elsesser:  Well, but I think it’s actually a really good Segway. Right? So, we’ve established now how important having a great deep domain is on your customer and on their industry, right? But, you were, I mean, for those that don’t know, Doug, you got to go check this out, but he once held, I think one of the most fun titles in the history of life, which was Chief Storyteller, which I think is like, what a great title. Right? What a great title at a very small company that no one knows called Box and right. And so, all right, it may be a little less small, but that, right. So, here’s my question. So, you’re now, you’re talking about empathy, you’re talking about understanding domain, you’re talking about leaving questions, the checkbox questions off to the side. How do you weave in storytelling? How does that work?

Doug Landis: That’s a great question. By the way, just to use a tip for everybody, I just broke my own rule. When someone asked you a question, never say that’s a great question, especially if you’re sitting on a panel, because now the assumption is, are you going to be judging the questions or one, or some are better than others? Because, they’re all great questions. Don’t ever say, that’s a great question. I totally glue it.

Bryan Elsesser:  Don’t worry about that.

Doug Landis:  It’s an appropriate question because one of the things that I talk often about in my storytelling workshops is actually learning how to get into and out of a story. The idea of storytelling is, I’m going to call it threefold. Number one, as human beings, we’re great storytellers naturally and automatically, but when it comes to work, we suck at it because we’re used to speaking in bullets and fragments and I’m going to call Twitter form, Twitter link text.

And so, we get to work and all of a sudden it’s like, ‘ah, how do I do this work?’ And yet, and then we leave. We’re like, ‘ah, that meeting was terrible’. And here’s why. Right. Because, we forgot the why piece when we were actually talking about our company, our product, our solution. And so, it’s really important to understand one, the story mechanics. And we’ll talk, we can talk about that in a second, but two also recognizing when to get into and out of a story. So, Bryan, back to our example, I’ve done all this research on the industry. I’ve got a point of view about your company, Bryan in oil and gas, and a point of view about you and your role, and some of the things that you’ve struggled with. I’ve got a customer and more two that I can use as an example, to help build credibility and demonstrate.

I have a feeling you’re similar to somebody else that I have worked with in the past. Now, how do I weave in a story there? I could do it right then and there. You know what, Bryan, as I was thinking about you at that, I’m just going to say, S Gas and Oil and, or Bryan’s Gas and Oil company. And, it reminded me of a conversation that I had with Jeff yesterday, who’s at Chevron and he’s the VP of Revenue there.

And, I’m just going to launch into a story about Jeff.  Right there, boom. I’m in, here’s the story about Jeff and his world, or here’s a story about our conversation, our experience, or here’s a story about my reaction. There are a million opportunities to tell stories in business conversations, but what often gets missed is number one, we haven’t thought about the audience who are speaking to, and therefore what stories are appropriate to are with you, Bryan, in this particular exchange.

Number two, we haven’t been thoughtful about the story that we’re going to tell. And more importantly, the point that we’re trying to make with the story.

The reason why people suck at telling stories at work is because, we ramble. We’re not thoughtful about the point that we want to make, and so you end up telling a nine minute diatribe and the person on the other hand is like, ‘where are you going with this?’

Bryan Elsesser:  Where’s this heading?

Doug Landis:   Why the hell is this taking so long? We’re just heading, what’s the point? And they’re asking that, but they’re just not saying it, so they’re checking out.

The third thing is, is you’re also not really clear about kind of the mechanics of the story itself. Like the arc, right? There is like, you got to know your audience, got to know your point. You got to know who the characters are. You got to know that there’s a setting a time and a place, that there’s an event that happens at turning point in a resolution.

Bryan Elsesser:  Right.

Doug Landis:   Just that storytelling 101 and then you got to practice. And we don’t think about practicing telling stories. Why? Because our customer stories that we have are written out as problem solution ROI.

Bryan Elsesser:  Well, I mean, and also because every other salesperson puts on their sales voice, ‘I’m going to turn out into my sales voice now’. Right? And, whereas selling is a human-human experience. And if I was to take the stories I tell at the dinnertime table, right, in the same way in some format that I do it, if I’m entertaining people, it’s the same thing, but I’m speaking to someone, right?

Doug Landis:  Totally, totally.

Bryan Elsesser:   Same exact thing. Here’s one of the call-outs that I think is a challenge. And, it’s an interesting point, right? Because, we’re talking about storytelling, we’ve even talked about education and being knowledgeable. I think like we have companies now like Gong and Chorus and like Executive Vision. We have the VanillaSoft, we have these engagement tools out there. Everyone’s measuring us. Right? SalesLoft, outreach, everyone’s got a measurement. And one of those measurements out there is talk time. How long are you talking versus your prospect talking.

Doug Landis:  Totally.

Bryan Elsesser:  And if we’re telling stories, how often are we talking more? So, what’s your thought on that? Because, Gong would tell me I need to let you speak at least 50 to 60% of the time.

Doug Landis: Totally. So, here’s the thing. I don’t agree with all those crazy metrics because it’s marketing material to get you to buy in their content. I mean, it’s honestly. Honestly, it’s like whether you talk for 50% or 60% of the time, guess what if I talk a little bit more, maybe it’s because you asked me some really compelling questions and we’re in, we’re engaged. You have no idea what’s happened leading up to that. So, let’s take those statistics and throw them out the window. She’s my friend. Sorry, leave that out.

What is this? Here’s the thing, stories don’t have to be long. You can tell a story in six words or less. The reality is, is its communication, it’s a vehicle communicate. People remember stories.

Bryan Elsesser:   There it is.

Doug Landis:  Because, stories evoke emotion, emotion, evokes action. Stories have emotion, that emotion evokes action because it triggers oxytocin in the body, a physiological response when someone’s telling a story. People do not remember facts and stats and bullets. So, why do we lead with slides that are full of bullets and stuff? I’m reframing from cussing, because I’m so passionate about this.

Doug Landis:  Because, the reality is just like, I can tell you a story about my life versus the sequence of events that’s happened in my life.

Doug Landis:  Very different. And so, and at the end of the day, I want you to remember what I’m trying to say to you, because you got to turn around and sell this internally.

Bryan Elsesser:  A 100%. And I think that, that’s the part that really resonated when I heard you tell this the first time a couple years ago. Right? Where you said people remember stories and I remember that because you started it with a story, you know what I mean?

Doug Landis:  Bingo.

Bryan Elsesser: A 100%.

Doug Landis:    As, I say facts fade story stick. Just remember that.

Bryan Elsesser:   I love that. Wow. So, okay. So wait. This has been a fire, fire conversation. Let’s summarize it real quick. Give me three key takeaways that the people at home need to know.

Doug Landis:    Cool. First one, do your homework on the industry and the personas that you know that you’re going to be speaking to know what they deal with, know what their world is like, know what their pains are, so you can build a point of view. Build a point of view with a customer in mind, so you can draw parallels and comparison and use them as your vehicle and your voice to build credibility and empathy versus yourself, because you don’t have enough of it. That’s number two. Number three, introduce stories all the time and your conversations. Just be really clear about who the audience is, what the point you’re trying to make and the structure of the story itself. And you do that and guess what people are going to remember you.

Bryan Elsesser:  All right. So, the last thing. Give me a piece of advice for someone that’s never told a story in their life on a sales call.

Doug Landis:  Everybody has, we do it. Everybody has, everybody has. So, just practice get better. Here’s a great exercise; for your team, have each person tell a story every week, just tell a story about a customer experience, a customer example of what you learned about a product, your own aha moment in a product, someone get up and tell a story and then call a timeout and then call on other people in the group to say, what was the point of that story and make sure it is in line with the person telling the story and that exercise right there will get you to pay more attention to whether or not you’re really clear about what it is you’re trying to communicate and to whom.

Bryan Elsesser:  Absolutely incredible. For those that want some resources, that extra resources for their team, there’s also incredible Ted talks on this topic, incredible articles on this topic. You can find Doug all over YouTube talking about this topic. Doug, this has been really tremendous.

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