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Quotable Podcast Episode #39: “Keep Your Message Human, See Your Sales Numbers Rise” with Doug Landis

Hosts: Kevin Micalizzi & Lynne Zaledonis
People respond to stories, even when they’re buying software. Join Doug Landis as he describes how good communication is at the heart of sales productivity and enablement. First learn from your customers how to tell a story that matters to them — not one that's mostly about you. Then thoroughly battle-test your messaging and positioning to determine what lens you should actually be speaking from. After all, tools and technology can get you to a customer, but what you say when someone responds is the difference between signing a deal or hearing, “Maybe later.”

Far too often positioning and messaging is about you, when it needs to be about your customers.”

Doug Landis | Growth Partner, Emergence Capital

Episode Transcript

Kevin Micalizzi: Today, we’ll be discussing startup growth strategies on the go-to-market side with Doug Landis, growth partner, Emergence Capital. Welcome, Doug.


Doug Landis: Thanks, Kevin. Hey, Lynn. Good to see you again.


Lynne Zaledonis: Hello, Doug.


Micalizzi: So, Doug, obviously, Lynn and I both know you. But for the listeners who aren’t familiar with you, would you tell us a little bit about yourself?


Landis: Absolutely. And the reason, to all the listeners, why I know Kevin and Lynn, is because I used to work at Salesforce for a long time. Yeah, so a little bit ago, I joined Emergence Capital as a growth partner. I’ve been a practitioner on the sales — productivity sales, namely — inside for the last 15 years at Google, and Salesforce, and at Box, and decided to jump ship and join the quote, unquote, dark side or the other side of the table, however you want to call it — the venture community mostly because I now have the opportunity to actually go work with all of our portfolio companies and to help them figure out ways to scale and grow, to help them think through kind of the go-to-market side of the business. And to me, it’s like doing what I did at Salesforce and at Box but at scale. And it’s so fun.


Micalizzi: Love it. I’m Kevin Micalizzi, Product Marketing Senior Manager at Salesforce and executive producer for the Quotable Podcast. I’m joined today by my co-host Lynn Zaledonis, VP of Product Marketing at Salesforce. Welcome, Lynn.


Zaledonis: Thanks. Great to be here.


Micalizzi: So, Doug, in terms of grown strategies on the go-to-market side, I’m sure you’re seeing patterns and there are certain trends that seem to happen over and over again. Do you want to give us a feel for kind of what you’re seeing?


Landis: Yeah. So I think the first thing is, before you can start to identify patterns, the first thing any company needs to do is identify where they are. We see a lot of companies at varying stages. And some of them are tech founder-led and some are go-to-market leaders. And depending upon the type of founders, depending upon the type of investment partners that you have, depending upon who your early hires were, will kind of designate where you are as an organization. Some companies, maybe they have a ton of traction with their customers but yet the investment that they need to make is more on the product side, right?


And then some other companies are super product-savvy and their product is really far along — way more advanced than anybody else. But they have no support on the go-to-market side, right? They need a VP of sales right away. And they need marketing. And they don’t know what the hell they’re doing on the go-to-market side. So part of it is, as a company, first, you have to identify where are you in your growth cycle, right? And then where do you need help? Outside of that identification process, there’s some really common  — we’ll call them kind of speed bumps or hurdles that most organizations will face over the course of their growth evolution, right?


And ideally, what are we all trying to do? We’re just trying to be like you guys. We’re trying to get to be like Salesforce all over again, a multibillion dollar SaaS company. So one of the biggest issues that every company struggles with, whether you’re a Series A or a Series D, it doesn’t really matter, is positioning and messaging. And far too many companies, what I feel like their positioning and messaging and what I notice — you look at their first-call deck — it’s all about them, right? And honestly — I’m going to pick on Salesforce for a minute — I actually did some searches for Salesforce first-call decks.


And I saw this app exchange deck that was, I don’t know, a couple months old. And the first slide was all about like, “Here’s our platform. And look at our 5 million customers.” And it was like, OK, maybe you guys can get away with it because you’re Salesforce. But everybody else, especially when you’re Series A and Series B, you have to talk about your customers and what you’ve learned from your customers over the time that you’ve been in existence, whether that’s a month, or six months, or six years.


The reality is, it’s your customers that actually give you credibility. You don’t get credibility right out of the gate. You’ve got to earn that, right? And once you have some credibility by identifying what you’ve learned from your customers, then you actually earn the right to go and do some discovery, and ask questions, and really build those connections and those relationships. But far too often, if you look at positioning and messaging, first of all, it’s full of a whole bunch of slang, right? I can’t tell you how many times we’ve heard about this, right?


It’s our language, not our customers’ — and it’s all about us. And the reality is, it needs to be about our customers. And we need to speak through their voice. And so I challenge everybody that’s listening to this to go take a look at their first-call deck. Have someone deliver their pitch to you. And listen as if you were an actual customer and tell me what you think they’re actually saying,  because just far too often, it’s just totally backwards — completely backwards.


Zaledonis: Absolutely. And it’s funny because we all know that at the heart of it. And you find yourself slipping into it because it’s so easy to talk about ourselves, personally and professionally.


Landis: Absolutely. But the irony is, it’s also what we’re trained to do, right? Shame on me building all these onboarding programs, and what do we do? It was like, here, let me just crank on the firehose and tell you everything you need to know about your company. And then guess what? It’s now up to you to regurgitate that and deliver that to your customers and prospects. The reality is, we almost need to turn onboarding on its head a little bit, too, right? And kind of put the customers — who are our customers? What do they look and feel like? What do they struggle with?


What kind of people actually work at those companies where they come from? How do they like to build rapport? I’ll tell you what. It’s different to go talk to somebody in Kansas or in the south versus someone up in the Pacific Northwest, right, or down in L.A. They’re just different animals. And kind of along the lines of positioning and messaging, we have a tendency of taking this kind of one-size-fits-all approach, right? And the other thing I would challenge everybody to do is talk to your SDRs and ask them what do they say. And then go talk to your AEs and ask them. And then go talk to marketing and ask them.


What’s amazing and what you’ll find is, everybody has something different to say. And again, it’s all self-centered, right, so certainly, [it’s] one of the first challenges that most companies will face, regardless of what stage they’re in.


Zaledonis: So I love that. Take a good look at yourself in the mirror and make sure you’re not talking about yourself. You’re talking about your customer. Let me get some more tactical advice there, though. We all have those good intentions. How do you go about that? And what about new companies that don’t have a lot of customers or you’re launching a new product where you don’t necessarily have customers. What do you suggest there?


Landis: Yeah. So I’ll address that in two different ways. Number one, if I don’t have any customers, then I have a thesis, right, that I’m building my company around. I’ve got an hypothesis. And guess what? My job is now to go validate that with customers, whether they’re alpha or beta customers. And in that validation process, I really, truly need to understand everything about my customer and what is it about our solution that really resonates with them. But at the end of the day, I’m going to challenge — and this is totally — I’m going to give Marc Benioff all the credit in the world.


But Marc is brilliant in that he gets everybody at Salesforce to not only think about the customer but your customer’s customer — because at the end of the day, that’s what we’re trying to enable, right? We’re trying to enable our customers to do more business with their customers, right? And that’s the litmus test. So even if you have no customers, then the question is, is OK, well, how are we going to improve the relationship between our customers and their customer? If we’re making them more efficient, cool. But how do their customers then benefit from that?


And then if we do have a handful of customers, and we’re going to say we’ve been at this for a few years — and we ran into this at Box — the next question was, OK, what value are we really delivering to our customers. Kind of the “so what,” right? We talk a lot about the 80 yards. So we’ll get somebody to the 20-yard line and then we’re kind of like, “OK. Here you go. We sold you this solution. Good luck.” But what I really want to know is, tell me about Mary, who is the mid-level marketing manager that maybe works for Coca-Cola and she lives in Kansas, right? How is her life different or better as a result of using our product?


What it really does is it takes your messaging to a human level, right? And that’s what people connect with, right? We all connect through stories. And we talk all day long in stories except for when we get to work. It’s our weekend self, right? Our weekends, it’s like we leave work and we talk to our friends and family. We go home and we tell stories like, “How was your day?” “Oh, Doug came back in the office today. It was great.” And then we get to work and what do we do? We talk in bullets, right, and fragmented sentences. And it’s all about projects and —


Zaledonis: And buzzwords and —


Landis: Totally.


Micalizzi: Definitely.


Landis: Totally. So I think it’s about getting kind of into that human element of your messaging and positioning.


Micalizzi: When I’ve heard you speak on this in the past, you’ve talked about looking at what’s unique about your users, which I think is a fascinating point because we’re not just saying, “Oh, our customers are these five recognizable brands.” You’re really trying to dig for something more relevant, more applicable in there.


Landis: Yeah. Well, I guess one of the things I’d look at is, I’m trying to identify the problems that my customers don’t know that are problems.


Micalizzi: Right.


Landis: Right? I’m trying to identify the things that they haven’t even thought of. If you think about ideally, that’s what we’re trying to do in selling, right? We’re trying to get our customers — we’re trying to teach them something, right? And guess what? We’ve got a lot of insight that we can pull from our existing customers. And that insight can hopefully teach our prospects.


It’s like, “There are some things that you might not have considered in your role, in your function.” And by the way, the important word is “might” because consultants use the word “might.” Unfortunately, terrible salespeople use words like, “you should,” right?


Micalizzi: Yeah.


Landis: There’s a little caveat there. There’s a little nugget. Use the word “might” and you sound like a consultant and get paid millions of dollars. But the reality is, is like, “Hey, listen. We’ve learned all of this, and these are things that you might not be aware of.”


And that’s a really teachable moment. But the reality is, is that they’re just problems that you’re aware of that your customers aren’t aware of.


Micalizzi: Right.


Landis: And that’s what we want to do is elevate those, because now all of the sudden, you come to me as a buyer as someone who is actually giving me something for my time.


Zaledonis: And it also is the difference between somebody who is in sales and somebody who is a consultant, right? I’m offering you data points, or information, or perhaps challenging you about transforming your business.


Landis: Yeah. Challenge your everyday thinking. Fortunately enough, I’ve been a buyer of technology for a long time. The moment someone comes to me either with a pitch, or a message, or an email, or whatever it is, the first thing that I think of is like, “OK, why the hell do I care? Why should I give two hoots,” right?


Zaledonis: Right.


Landis: And so if it’s not something that’s connected or related to me, if it’s not something that allows me to learn even in a micro-moment, then you lose my interest, right, because now all of a sudden, I categorize you as just like everybody else, right?


Zaledonis: Yeah.


Landis: Just like Salesforce. You’re just like DropBox. You’re just like, you know —


Zaledonis: You talked about this being one of the big speed bumps that people hit, right, this messaging, positioning? But I’m also hearing a little bit of enablement because I have to convey that to —


Landis: Yeah.


Zaledonis: — my executive army — my account executive army to be able to take that messaging that we at corporate and where the founder or the leadership has and be able to tell that story.


Landis: Yeah, yeah. And it’s interesting because enablement here at Salesforce, what, you all — the team is like 120 people. When I was here, it was two of us. And the truth is, though, enablement is something that needs to happen from day one. I don’t care if you have 10 employees. You need to be thinking about this whole notion of enablement, although I’m going to take a step back and not call it enablement. I’m really sick of that word because it’s a marketing work. Sales enablement usually lives in marketing because you’re creating assets for the sales organization to go out and use. Sales productivity is really all about, how do I actually give you more time in front of your customers?


How do I help you do more with the time that you actually have, right? And the truth is, is you need to be thinking about this from the very early days, whether that’s testing and validating your messaging and positioning. And maybe you’re testing and validating it to different roles, to different personas, to different industries, for different roles within your organization like what’s your SDRs say, versus your AEs, versus your CEO or board. So some of that’s kind of that testing phase.


But you also need to think about, “Well, how are we capturing all these best practices,” right? You’re 10 people, you’re just trying everything, right? And maybe you’re going to conferences and you’re actually learning tips and tricks and you’re going to go try that. How are you capturing all that insight as far as what works and what doesn’t work because once you start to scale and you start to hire, those are the things that you want to share, right, because you want that to become kind of your repeatable process. And so enablement to me is really all about capturing all the stuff that works, and oh, by the way, capturing the things that don’t work.


Micalizzi: Right.


Landis: Right, because if you forget about that, then you’re like, “Oh, wait. Let’s try that. Well, no, we did that a year ago and it didn’t work.” That’s not to say that it couldn’t work. Maybe it didn’t work because it wasn’t the right time, but capturing those best practices and then learning how to share those across the organization. And then, of course, I think you get to a certain point where you’ve got to start thinking about, “Well, how are we onboarding,” right? “How are we getting our reps up to speed as quickly as possible? How are we certifying everybody on this message?”


And the moment you start to get an enterprise team where you have people out in field, it’s like, “Wow, that is a whole another animal in terms of enablement,” right, because you’ve now got just engagement issues, right? So do we keep them for onboarding session, is it two weeks? Is it a week? Is it a week? Is it 12 weeks and the next 11 weeks are kind of elearning type of content? And you’ve got to think those things through. Enablement’s massively important. I’m a big believer that sales ops and sales enablement are hires that you need to make earlier than you think.


Zaledonis: Well, that sort of brings up what I thought where you were headed, which is another speed bump. It’s got to be scaling your organization.


Landis: Yeah.


Zaledonis: It’s got to be hiring and onboarding — all these things you just talked about.


Landis: Yeah, totally. So, yeah. So three speed bumps — one, positioning and messaging, two, hiring, for sure, three, enablement and sales operations, right? They all fit together, right?


Zaledonis: Right.


Micalizzi: Right.


Landis: Because if you get your messaging and positioning right, then hopefully, that’s going to allow you to go out and get some more customers, so you’re going to need to hire more AEs to go scale. And then you’re going to need to onboard, and train, and enable them, right? It’s all totally interconnected.


Zaledonis: So when is too soon? When do you start thinking about those different roles? Do you have a formula for that, or does that depend on the company?


Landis: Some of the numbers that I’ve gotten actually from Salesforce — it’s kind of funny, I was just recently thinking about this. I’d say first and foremost, hire sales ops functions, a sales ops leader because you need to be thinking about territories, accounts, quotas, comp plans. All that stuff actually, those are the things that keep a rep from wanting to go do work, right? I need to know how I’m going to get paid, how much I’m going to get paid, and where is my opportunity, right? Where’s my green field? Where are my upsells, because that’s an incentive for me as a rep. It’s super important to get kind of operations functional.


In addition, you also need to make sure that your CRM, your Salesforce, is set up and it’s clean, right? And there is some statistic that you guys put out that says if you are less than 30 users — 30 users or less, you need just under a full-times Salesforce administrator. If you’re 30 to 70 users, you need one and a half Salesforce administrators, right? And that’s typically one of the first operations hires that you may, anyway. You’re like, “This is our system of record so we need someone to help us manage it and then build on it,” right?


But it’s interesting, the numbers roughly are for every 20 AEs, you need a sales ops person, right? It’s super important. So I don’t actually think you need a full-time sales productivity or sales enablement person until you’re about maybe, well, call them — I don’t know, maybe 30 reps in total — kind of multiple functions. And you could probably start off with a junior person to help with onboarding and capturing your best practices. And then maybe the messaging and positioning stuff is handled and managed by your product marketing team.


Once you really start to scale beyond that, once you’re like a hundred reps, you have to have a productivity strategy. And it has to be aligned with sales operations and your VP of sales, really.


Micalizzi: I know one thing I’ve heard you speak about in the past is the challenge we run into with new, especially like RVPs of sales and how to get them up to speed. If I remember right, you said no one bothers training a new RVP on how to be an RVP. What have you been finding works?


Landis: Yeah, right? Lynn is over here shaking her head because it reminds me of the early days of Salesforce where we’re basically just promoting reps up into managers. And we were like, “Yeah, good luck,” right? And fortunately, we were so process-oriented here at Salesforce that it was pretty easy to kind of latch onto the process. But I think there are nuances to becoming a great manager that are often overlooked, right? I think the marquee — the foundation of what makes a great manager, is threefold, right? Number one, first and foremost, you’re kind of a company manager, which means you know how to dig into the data and actually roll up all that data — your forecast, etcetera, territories, and what is your hiring plan?


You know how to roll all that up and present it up, right, to your sales leadership or to the board — maybe your investors. The second is actually being a closer — closing manager — like helping your reps learn how to close big deals or bigger deals than what they’re normally used to. And part of that is actually getting into the health of the deal and getting into helping them identify the signals and the indicators that you’re aware of that help determine whether or not this is a healthy deal. And then the third thing is that kind of cheerleader, right? The cheerleader is like building culture and they’re doing all the awards and what have you.


What’s interesting is, I would challenge everybody that’s listening to this to go back and look at all of your frontline managers and try and identify where they’re stronger, because most often, you’ll find that people are stronger in one area and weaker in the other two. So then the question is, how do you get better at all three? If I’m a great company manager, I’m a numbers guy, I’m in the weeds all the time, and I know all the numbers, but I don’t spend any time with my team coaching and developing, well, guess what? They’re going to feel neglected. And most likely, they’re actually not going to perform.


But how do I get better at coaching? How do I get better at building time for those one-on-ones and kind of building that culture and camaraderie? It’s something you need to learn, right? But it’s also something you need to be aware of. And nobody trains anything about like, “Here are the core elements that make for a great frontline manager,” which I believe there is a huge opportunity.


Zaledonis: Are any of those more important that the other, or are you just looking for a blend of all three?


Landis: I think ideally you want a blend of all three, right? And part of it also comes back to the culture of the company.


Zaledonis: Sure.


Landis: Right? And the founders and the leadership — some of our companies, they’re so culture-driven that it’s ingrained to the entire organization. I’d say for them, it’s probably more about becoming better company managers, yet really digging into the numbers and knowing the business because they got the culture and they got the coaching side of it down. They also kind of have the deal side because that’s more natural to us, right? If we’re a former AE somewhere and we progress up to an RVP, we understand kind of deal mechanics a lot more.


So I tend to find that it’s either the culture, the company, or the numbers side that tends to be a little on the weaker end. But it kind of goes back to this. If you look at the hurdles, messaging and positioning, hiring, and enablement of operations, well, hiring, right? Frontline sales managers are crucial hires. One of the things I find most often people struggle with is like, “When do I hire the VP of sales? How many AEs do I need before I actually have to start building it in layers? I just need to scale, right? I just need to hire a bunch of people.”


What most people don’t actually sit down and really think about is, “Well, what does that hiring profile look like? What do you really need? How do you know that this person is going to be great,” right? And I think a lot of people have a tendency of taking this peanut-butter approach. It’s like, “Oh, you’re a great, successful AE at Salesforce. So sure, come on over here.” And honestly enough, I would argue against that. If you’re an early-stage startup, don’t hire an ex-Salesforce AE. Just don’t. No offense. Of course, there’s caveats to all of this.


Zaledonis: Now there’s people really upset everywhere.


Landis: I know. I’m pissing everybody off. But think about this. At Salesforce, you’re used to having things kind of handed to you. And my job is to take this little opportunity that you handed to me and blow this thing up. The truth is, if you’re in an early stage, I need an AE that’s going to roll up their sleeves, try everything, they’re super business-savvy, super-smart, right? Not just like, “I know how to go out and sell,” because in the early stages, you need to wear a lot of hats.


And it’s like, “Oh, wait. I want to help us to build some process,” or “I want to help us to define what our right profile looks like for our AEs or think through our pricing strategy,” right? You want those kind of what they call the athletes, right? Those kind of universal players in the early days.


Zaledonis: You brought up CRM solution earlier. And all brands aside, what are the technologies that companies who are going through this transition, and growing, and scaling, what technologies are key for a sales organization in these early stages to get over these — beat hurdles or to get out to market faster?


Landis: Yeah. So the technologies that we see a lot of — I’m going to put them in categories, right, because there’s a bazillion companies in every category, really. Of course, CRM is your system of record. Most of the companies we talk to are Salesforce customers, although in the early days, you might start off maybe with SalesforceIQ — I keep thinking of relateIQ — because you need something lightweight, right? And then eventually, it’s almost like everybody already knows that they are going to scale up to Salesforce. But outside of your system of record, I think categorically, there are some areas that you need.


You need some sort of — we’ll call it email communication platform, the likes of a SalesLoft, or a Tout, Yesware, right? It’s like, “How am I communicating efficiently with my customers in a cadence?” because we all know that every sales opportunity, what, there’s somewhere between five and seven buyers. And it takes anywhere from five to eight touches in order for someone to respond. You need to set that up into a cadence of communication that’s appropriate, whether that’s a call, or email, or a tweet, right? And so that’s a really, really important layer.


I think there’s also a data layer that’s also really important, right? Where are we going to get additional contacts, whether that’s Data.com, or DiscoverOrg, like LeanData, right? So in the data layer, not only do you have the contacts piece but you also have: How do I ensure that I’m cleaning up the data that I’m bringing in, right? Maybe I’m bringing in lists or I’m doing webinars and events, and I’m pulling all of these people in. And I want to make sure again, my CRM is clean. Super important. I think a lot of people forget about that as they’re building their stack, is like, “What is your cleansing layer?” because if you don’t think about that, things get messy.


Zaledonis: Fast.


Landis: Yeah. And it just gets worse, right? It’s like the ripple effects if you don’t think about that. And I would also argue doing a lot of customization in your Salesforce and your CRM is dangerous because it could lead to some scale issues in the future. Nowadays, I would also say there’s a communication layer that’s really, really important outside of kind of email and phone, which is really all about in learning and development, which is the likes of web conferencing. You could use Zoom or the likes of the Choruses of the world that are recording your calls. This is the kind of coaching, training opportunities.


I kind of put that also in the communication bucket, right? There’s the email, and then there’s the phone, and there’s kind of learning. I’d also throw in there are also some learning platforms that you need to think about, right? I’m going to piss a bunch of people off right now, but I think the traditional LMS is kind of dead. It works well for companies that need to sell education and that want to use it as a platform for engaging with partners and customers. But for internal learning, especially on the sales side, it’s very different. It’s much more of a certification platform.


And we’re seeing a lot of those out there, the likes of the LearnCores of the world and good, old Elay [Cohen]’s SalesHood, and MindTickle, and others. But you’re really trying to drive consistency of messaging and story, and especially as you’re scaling outside of your headquarters location, those are a handful that I can think of right of the bat. I’m sure —


Zaledonis: Great. No.


Landis: — I’m missing a ton.


Zaledonis: No, that’s good. I think people want some of that tactical information about what they should be thinking about.


Landis: Yeah.


Micalizzi: Absolutely. So let me ask you, Doug, what parting thoughts would you like to leave our listeners with? My thinking is, soon as they finish listening to this podcast, what should they be going to do right away?


Landis: Yeah. First thing I’d say is go back and check on your messaging and positioning. Just battle-test the hell out of that thing with your customers and with prospects. And try and just see if you can determine what lens you’re actually speaking from. The reason why I bring this up and it’s so important is because, look, all of these tools and technology that we just talked about, they can get you to a customer. But what you actually say when someone responds is the difference between creating an opportunity and closing a deal versus getting the, “No, thanks, not now,” the typical objections that we hear.


So I’d say go battle-test that out and then really look for the little nuggets from your customers that you can infuse in there. And then, additionally, kind of like my marquee books that I keep falling back on, Mark Roberge’s book The Sales Acceleration Formula, love that. Ton of nuggets in that. "Go Mark!" Especially because all the proceeds go to his foundation and nonprofit, which I have mad respect for. And then secondarily, an old-school book called Made to Stick, if you want some ideas around kind of messaging and positioning. It’s an awesome, awesome book to give you some little nuggets of insight to help you rethink your messaging.


Micalizzi: What’s your favorite blog?


Landis: Mine.


Micalizzi: I love it.


Zaledonis: Go ahead and promote it.


Micalizzi: Yeah, totally.


Landis: Yeah, yeah. Well, keep your eyes out on The SaaS Playbook. We, at Emergence Capital, we’re launching a really cool playbook that’s just nothing short of a litany of models that you can actually use. It’s especially helpful for Series A and B startups. And then my podcast that’s coming out called What’s Your Story? starts soon.


Micalizzi: Perfect. Awesome. Thank you so much for joining us, Doug.


Landis: Of course. It’s great to be here. It’s good to see you guys. Good to be back home.


Micalizzi: And, Lynn, thanks for joining me to co-host today.


Zaledonis: Of course, Kevin. And thanks a lot, Doug. Welcome back.

Micalizzi: And for those of you listening in, remember, the best way to learn from the best is to subscribe at quotable.com/subscribe.

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