Voiceover: What does it take to stay ahead in B2B SaaS? Welcome to The New Go-To-Market Playbook. I'm your host, James Kaikis, Chief Revenue and Experience Officer at Testbox. In our interview series, I sit down with go-to-market operators, leaders, and industry experts who are defining the next era of go-to-market by winning in the margins. These leaders are focused on incremental innovations and non-obvious advantages that drive big results. The goal of this interview series is for you to take action in your business. So sit back, grab a notepad and enjoy the episode.

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James Kaikis: David, great to see you. Thanks for joining me. 

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‍David Yockelson: My pleasure to be here. And it's nice to actually physically meet you in person. 

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James Kaikis: It's been the common theme of this interview series—so many people that I've met virtually over the last couple years, even with PreSales Collective, where I’ve built relationships, talked to people for years and never met in person. So it's great to finally meet you in person. So it's great to see and thanks for joining me. I was reflecting back on how we got to know each other. So after I left PreSales Collective and was doing a bunch of research on the space, I had seen that you were putting out so much content on demo automation and interactive demonstration applications. And I was like, oh, I need to reach out to him and pick his brain. So I think that's how we met maybe a year and a half ago at this point. 

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David Yockelson: Sounds about right to me. Hot in the midst of a quickly growing and evolving space. 

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James Kaikis: And it continues to do so. So yeah. And I again, appreciate your expertise and appreciate all that you're doing for the category. But let's talk about you for a moment, right? Tell us a little bit about yourself, your role, company that you're at, where your focus is. 

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David Yockelson: So I am at the Big G, I'm at Gartner. I work in a part of Gartner that I think not as many people are familiar with. So most people know Gartner as the magic quadrant people and the tech influencers and so on. For the most part, I don't do that. So my job is I work exclusively with tech companies and I and the team that I'm on help them with go-to-market, so aspects of marketing to demand gen, sales, et cetera. Now, it turns out there are a few technologies (well actually a lot!) part of go-to-market, but there are a few that I've kind of locked into for whatever reason, interactive demo/demo automation being a big one. And so my job becomes twofold. One is help them figure out what they need to do to be in-market successfully and drive pipeline and successfully win customers. And then what are the technologies that they can employ to do that and do that more effectively?

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James Kaikis: Yeah, one of the most interesting things about your job is you probably get to work with so many different companies, big, small, and you get to learn a lot about what's working and what's not working. Is there something right now that's been top of mind on a lot of different companies?

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David Yockelson: Yeah, I think the constant refrain is “how do we drive pipeline better?” which gets spoken about and asked about in a lot of different ways. But from the marketing perspective, it's how can we be more effective and efficient with sales and how do we drive and manage that alignment? And from the sales perspective, it's that we want to do more with less. I think they want to do less with less, but which means getting to a point of precision, figuring out what accounts they should target and what they should say to them, and then obviously convert them at a better rate than they have here.

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James Kaikis: I think that's a really interesting topic generally, because it's been something that I've talked about with a number of folks of how the marketing role is also changing from the “let’s not think about MQLs and SQLs, let’s think about pipeline and rev gen. 

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David Yockelson: Spot on, I did a marketing roundtable last week with senior demand gen leaders, senior marketing leaders, and one person said,”you know, my job is I have to drive 10,000 MQLs a month. And I said, well, what if 9,000 of them are terrible? So exactly. And that's the mindset — you're absolutely right— that we have to get out of. 

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James Kaikis: I will say as a solutions leader who turned entrepreneur to now running go-to-market, that was one of the first things that I did was get rid of this concept of MQL or SQL because I found out when I joined Testbox that we looked at demo requests as the success of marketing, but when I dove into the data, most of those deals were unqualified because people thought we were product tours. And I was like, okay, I don't care if we get 50 demo requests a month, if only two of them move to stage two or stage three, I'd rather get five and have four of them move to stage two and stage three. And I think that reframe needs to common in go-to-market.

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David Yockelson: I could give you chapter and verse that you well know on segmentation, ICP, stick to your ICP, all of that. And then some companies do really well, some don't. One of my favorite conversations I have with companies is when we're talking about product led growth, the number of companies that as soon as somebody signs up for a free trial, they get pounced on by sales, which defeats the entire purpose of the whole thing. So my refrain is a free trial is not a lead. I mean, we could spend an hour talking about this. 

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James Kaikis: Let's dig in a little bit, right? Tell me more about what that means.

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David Yockelson: Yeah, so again, if you're gonna give away some access to a product or provide a product experience, just the fact that somebody filled out the form doesn't make thema qualified lead. So what does make them a lead? What makes them an opportunity? So In PLG, we have the notion of a product-qualified lead, and all it means is that somebody has done the right things with the product, consumed a set of features, spent time, used templates to the integration, whatever that means for that product in that category, but they've done enough of it to see value from it. And so there's another little nuance about aha moment versus PQL, and anyway. But that's what it means. So at the point that conceptually that person and people within an account have done enough to see value, that's a lead. And that's the point at which now it makes sense to make them an offer or have sales outreach, something like that.

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James Kaikis: Why do you think companies are getting PLG wrong?

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David Yockelson: So I think the first place that it starts going wrong is the interpretation of what PLG is. So, and I had a fun LinkedIn argument about that this week where somebody said, PLG isn't worth it 98% of the time. Well, why not? Because most people come into it thinking PLG automatically means 100% self-serve. And it can't, and it should not. So that's mistake number one. Okay, we get past that. Now, we have to decide is our product and audience combination right to provide a free trial if we want to do that, or offer a freemium version if we want, and by the way, does our pricing work well enough to do that? I can give you a couple of examples of very large portfolio companies that come to me and they say, "We want to do PLG." Okay, among the 30 products you have, which one? And they all have different buyer personas and ICP so that's another problem. Third problem is, let's say we get to the point of having a free offer. You can't assume that a user of that thing is gonna do the right things, the right feature consumption, the right activities, or fulfill the right use case in order to see value from it. So the mistake is that they're not guided along the way to doing the right things. They get dumped into a something. And then the last thing that I alluded to is PLG is really about the user, not the buyer. Particularly for companies that have established marketing and sales functions and motions, they're used to talking to buyers. And it's an entirely different mindset. It's an entirely different journey. It's entirely different digital marketing, SEO, all of that. 

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James Kaikis: Yeah, what I realized at Pre -Sales Collective, and I may have told you this before, I would talk to companies like, "Oh, we're doing PLG, we're doing PLG." But if you don't think about the first-time user experience, are you really doing PLG? 

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David Yockelson: Yeah, I mean, so I kind of assume wrongly, and you're absolutely right, that product’s got a great UX. 

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James Kaikis: One of the things that we've talked about in general is signals, right? Signals tend to be a hot topic right now. I think there's a lot of products entering into the space. What's your general thesis of signal-based selling and that category that's getting more and more popular? 

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David Yockelson: I think the question I'm asking myself with it is, is it driving or can it drive marketing and sales closer together? Or does it drive farther apart? I think it's very cool stuff for a variety of reasons. If we go back to the do less with less thing, I think sellers and sales teams in general are pressed to figure out which accounts are gonna represent the best opportunity to close business and it's hard, especially if what they're being handed is this big bunch of perhaps less than well-qualified leads. So that's number one, they have to figure that out. The other aspect is that, you know, cold outreach … I'm not gonna say that cold outreach is dead. And SDRs are not dead. I mean, they're solely being automated, but it's still a thing. But warm outreach is so much better. If you can, you know, have the right conversation with a prospect based on things that you know they did with your product and your community relative to social postings, all that sort of stuff, then you're that much closer to being in their context. And that's the general point around the signals. And I think the other aspect of it is that it becomes a better version of lead scoring that everybody has done traditionally. But the data that you're using to derive the scores is better, it's better at the individual level. 

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James Kaikis: I like that a lot and I think what we've been talking about in our business is what is a real signal right and how do you weight the signals right because just because somebody's on your website doesn't make it a signal and I think this is what I'm trying to keep my pulse on is like where do you weight the signals. Let's use LinkedIn for example: I can't really see you which people and which companies are liking all of my posts, our companies posts, our employees’ posts because those tend to be signals that I think would influence a purchase decision. 

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David Yockelson: Yeah, you could even take the LinkedIn postings and answers and grade them independently. Each of them represents a different kind of a signal. So one of the vendors talks about signal stacking, which again, is you're making a judgment of which ones mean the most given, what you do, what that person is doing, who that person is, and inferring what sort of persona that is, is it your buyer, is it not, and what can you amass about not only that person, but about the account. So resolving the individual up to the account level, enriching that data, which is done a variety of different ways, but doing that so that you have a much better picture of what's going on in the account, and you can kind of, I'll say, enhance your ABM experience. So this is not a replacement for ABM, it's an adjunct. 

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James Kaikis: I like that. I love the do less with less. I actually haven't heard that one yet, and I think it makes a lot of sense. But I want to talk about another area where you're an expert, right? And this is interactive demonstrations. I have to ask, demo automation, interactive demonstrations, why do you think there's this difference in the naming?

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David Yockelson: I'll tell you why I think it happened and what I think they each represent and I'll tell you why I chose the one that I did. So inception of the space was focused primarily around making SEs lives easier. So what is one of the jobs of the many that they have? it's creating demos. So demo automation naturally became the technology that helps automate the way that they can create and serve up demos. Which is fine, and that's an incredibly valuable thing. But my perspective is that there's a whole other world at the top of the funnel, a more marketing oriented use case. And if you look at it from the buyer's perspective, what do they want? They want an interactive experience. That's why people put videos on websites. So to me, the notion of interactive demo accented more what the buyer or prospect is looking to get and the thing that would benefit them. 

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James Kaikis: I appreciate that. And I know that we've had a little bit of back and forth on the title and the name. And I think even for us at Testbox, trying to figure out what is the category, right? And what's encompassing in the category. So one of the things that I would love to get your perspective on is how much change you've seen in this category over the last couple of years, right? Because, you know, going back to my background for those who don't know is when I was at PreSales Collective, most of these companies were born and they were trying to sell to SEs, whether they were, you know, like the product tour screenshots or something else, they were trying to sell solutions and we had that audience and so we partnered with a number of these companies. We've seen that shift a bit in the last couple of years, but I'm curious from your perspective, like what have you seen that has just been so interesting that has allowed this space to explode? 

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David Yockelson: I could be sensational or sort of negative and say, well, it's so easy to build. That's why this is like that. It's really not. If you're doing it right and you're covering a range of activities, it's not. We can talk about that. But if we step back, the companies that came into the space originally were very religious about the use cases and the buyers that they were going after. So to your point, there were companies that said we are going after sales, I don't want to hear about marketing. In fact, marketing gets in our way, and I don't want to deal with that. And then there were the companies that were exactly the inverse, we're going after marketing, the salespeople can do what they want. And so one of the things that's happened is both sides have gradually recognized the value on the other side, and not only on their own, it's their customers that are driving them to it. So there are lots of situations where one part of the company has one product, another one has another one. And the technology has evolved also in the last quick span of two years, where it generally works well, and the vendors generally address more than a single use case. So even the companies that started with a product are now looking and saying hey do I want to deal with these use cases, do I have the right thing, but I don't want to have three of them. Can I have less? So that's what's happened. I think the other stuff that I wouldn't say is a big change. This has been a continuum of buyers not wanting to talk, at least initially, to sellers. And that's why PLG is a thing. Arguably, Interactive Demo, Demo Automation is a derivative of product-led growth. And for those companies that can't provide a free trial or a freemium offer, this is the way to go. What I’ll contradict it with is that it turns out the efficacy of this technology in leading to free trials is huge and then within free trials driving engagement. It's huge. Why? Because it removes the mystery around what it is, what it does and what is should be doing. The thing that resonates with clients that I talked to and is that this technology is a hammer and like everything in sales and marketing is a nail which normally would be bad. So we have buyers not wanting to talk to sellers. We have sales cycles that on average last 10 months. We have companies that have prospects that get stuck mid funnel. They're not sure what to do with them. So on and so forth. And so a lot of the conversations I have about the technology, don't start with the technology. They start with a sales problem. Or a marketing conversion website problem. 

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James Kaikis: Thanks for that. You made a point at the beginning that I think is really important. And I was actually talking to the team in Navattic about this the other day, is that a lot of folks from the outside tend to think that building these products is easy. But that is actually not the case. So I'm curious your thoughts because whatever you're doing, product tours, live demos, proof of concept … these are very, very challenging technologies that are actually very complex.  We've seen a massive amount of entrants, especially in the product tour space. So I'm curious, right? 'Cause like, ideally those concepts kind of contradict each other, right? Because it's not as easy. So I'm curious like what you've seen and why you've seen so many entrants in the product tour space. 

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David Yockelson: It's not a hard technology to build at the low end of it. At the, what we'll call screen capture level, that's easy enough to do. Now, it's been added to and dressed up with analytics and has the guidance and hotspotting and panning and zooming and all the stuff that goes along with that - and throw AI into it. So those environments and products have evolved. Well, let's think about it in terms of what I now often call a product experience. So this technology, whether we call it interactive demo, demo automation, what it's trying to do is provide the right product experience to the right person showing up within a buying process. It's one thing to show the screens of your product on a web page. It's another thing to say, Hey, I now have two people, and I want to show off how this works in a context in which they need to use it and they want to see it. That demands higher fidelity. It demands the ability to customize data. So as you progress through the funnel, through a buying process, whatever the need for that fidelity and the need to approach something that's more like a POC becomes more important. And the degree of difficulty in building a product that can mimic the product becomes more difficult. 

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James Kaikis: So one of the things that I've always thought, even when I started my research, is that the space can be so confusing, right? So Gartner, you've broken down this space into four categories, is that correct? 

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David Yockelson: That's right and every day it becomes like a four and a half or a four and a two thirds.Because I could debate that one too. 

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James Kaikis: So what are those categories and how are they different?

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David Yockelson: Yeah, so the way that, just to retain my own sanity and to try to be helpful to people what I try to do is say there are four, generally speaking, there are four ways to create interactive demos. One is based on video, one is based on screen capture, one is based on overlay on a production environment, and the other is, we'll call a sandbox. The four and a half to six, there are little differences in how the overlays, in the sandbox and so on are created and implemented, but those are the kind of the four. It turns out that also each of those four are useful in different use cases. So you don't always need each one. From the interactive demo vendor’s perspective, the more of those you can handle, the stronger you'll be long-term. 

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James Kaikis: That's a really interesting topic and I was going to actually ask you about this anyway. From my perspective at Testbox, we actually are actively choosing not to do screen capture or product tour. We only want to be in live demo. We only want to be in POC/sandbox. And that's because the buyer in our ICP is very different. And what I have seen firsthand in this space is that, like you kind of said earlier, like you're doing product tours for marketing and their wants and needs and live demos have another audience. So where do you see and why do you see the vision in the future of like one vendor that can handle everything? 

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David Yockelson: It’s where one thinks the revenue is. So if we go back to the birth of the category, companies said we think all the revenue is going to be on the sales side and they can charge more and drive a bigger ticket. When you have a legion of sellers that you can charge per seat. That doesn't work on the marketing side. So sure so you know in some respect you you pick your poison. But you know there are those companies in this space that say, listen we want to service the span of different occasions across a buying process. 

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James Kaikis: Do you think companies are saying that they want to service all these categories, but the way that they're servicing them does not actually compare with what the rest of the category is? So let me break that down, right? So for us at Testbox, we're a live data, data-focused organization, right? We're one of the only companies, if not the only company taking that approach, right? I have heard other folks tell me, "Hey, this product tour company can do live demos." But it's not necessarily live demos, right? I will say, and I'm not afraid to say this publicly, I have seen this space and multiple iterations of this space. And frankly I can say this because I was part of the problem, I'll admit this, because when the space started, I saw a lot of these companies that are product tours or screenshots selling to sales team, and now they're having crazy attrition and churn because they oversold and I'm afraid that cycle is beginning again but I'm curious what you think.

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David Yockelson: We can all look back on my LinkedIn post about live. So live can mean a couple of different things. One definition of live is two people or one to many, one to one, in a live situation where things are happening rather than a self -serve, guided tour, guided whatever. That's one aspect of live. The second aspect of live is with respect to the product. It's the real product. Or as close to the real product as you wanna get. I agree with your point that, and this is part of the evolution of the space that a couple years ago, there weren't that many options. But anything was so much better for the SE that they would go and do that. So now there are more options, and I think people are going to scrutinize much more closely. Hey, for this situation, we need the highest fidelity version of our fake product that we can get. And by the way, we have to fill it with data because we've got to do this demo a thousand times a month. So yeah, that's where the difference is going to be. 

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James Kaikis: Yeah, I appreciate that perspective and I think as I just reflect back on my own journey, one of the reasons why I came to this category amd space was that I wanted to help build a category. And I wanted to help bring clarity and I think I saw and I'll admit I was probably part of the problem, I didn't realize that of like some of the overselling that's happened and I think where I have already seen this at TestBox is we've talked to people who are like, "Oh, I've been burned already by somebody else." And we have to say like, "No, we're doing it differently," and show them that. And so I think that is what I'm trying to figure out is like, is the category in its own way? And this is why at Testbox, and not to too much about us, we're trying to partner with, you know, other companies to bring more clarity so that buyers are educated on the nuances.

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David Yockelson: I'm a marketer, product marketer by trade. So I'm used to embellishing story about my products and so on. But I don't think it's intentional misdirection. My view is I think that almost all of the companies have not done a great job of explaining what my little grid tries to do and doesn't really do that well either. Yeah, there's gotta be a pairing of, okay, we supply four methods to create demos. And this method is best for this situation for these sorts of folks that show up. This one is best for that, that one's best for that. There's been some of that, but I think either it's not out there loud enough, or when it's supplied by a vendor the buyer takes it with a grain of salt. I’m trying my best. I can only write so many things, you know, in so much time. But that's where I think that we have to get to. We have to be able to explain, just like I would tell on the go-to-market side, the value of what you're offering is it's going to solve this kind of problem. We’ve got to talk about the problems that it solves.

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James Kaikis: Thanks for that. And I, again, appreciate all the work that you're doing to help bring awareness and clarity. What do you think about AI in this space? We've talked about this a little bit. And it's been a common thread in a number of my conversations recently, so I'm curious about your take. 

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David Yockelson: Is there actually a conversation you can have that doesn't have AI in it? This is my anecdotal reaction, I think it's valuable in a few places. I'm not sure that the uptake is extreme yet. Okay, so where is it useful? It's useful in translation. I think that's probably most broadly used implemented utility so far in this space. I don't know if I'm a fan yet of script creation and that sort of thing or there are a few companies that say, "Hey, let's consume your website and I'm going to pop out a baseline demo for you." Pretty cool. It's coming. We’ll get there. My view is, I think that the best use of AI is going to be with respect to data. And so the ability to create synthetic data easily, quickly, populate an application, whether it's a captured version of that or it's a live version of that, but do that and do it repeatedly or have it at a click so that seller A can run the oil and gas demo. So that seller B can run the healthcare demo, that kind of thing. 

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James Kaikis: Biasedly, I think that's the future of this space as well. So I think what's so interesting generally is where this space continues to evolve and where the value is, right? Because I think that, again, going back to TestBox, we've taken an approach where we're trying to replace a demo environment, right? And we do not think that you need to have a team of people managing demo environments and product and engineers. And if I put myself in my old solution shoes of being like, hey, if I can have people and headcount that are talking to customers versus like scaling people on people, that is very appealing to me. And that's a very different concept. And even though folks that are in my network and I say, hey, like, we want to envision you not owning and imagine your demo environment, and that scares people. 

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David Yockelson: So there are companies that have the, call them the demos czar, or the person that is in charge of the product experience is whatever shape and form, because we don't want the Wild West. We want some control over what it is people are doing. But I think there are other companies that will say, to your point, I don't want to spare the headcount. I want the mess. And my SEs are understaffed as far as SEs or solutions people as it is. And let them go talk integration and past customer experience and help verticalize what we're doing and that kind of thing and then move the headache away. 

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James Kaikis: Let’s shift our focus to the category generally, right? Like, how big do you think the TAM is? 

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David Yockelson: So I've arrived at a number both than a back of a decent envelope exercise and in conversations with folks. I'm pretty happy saying it's probably in the eight billion dollar range. Between seven and nine is where things have kind of come down. 

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James Kaikis: Where do you see this space in this category evolving over the next three, four years? 

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David Yockelson: Like we talked about before, I think that you're going to see more broadening of capability among most of the vendors in the space. Sorry, I shouldn't step back. I say most of the vendors. How many vendors are in this space, David? There's over 30, let's say, and it's not quite the pace that it was two years ago, where every week it's three more, but there's a lot. There won't be a lot in two years for a variety of reasons that we all know. So compression is going to be number one. As we talk about it, like I said, I think that there are going to be vendors that say, listen, our strength is here. We want to span the range of those product experiences and we're going to invest to do that. I think the point about AI is a good one. I think the faster and easier ability to create a demo by consuming a video, a website or whatever and then generate a decent starting point. I talked about the data I think is really important. The other, I don't know if it's the space evolution or it's the taking advantage of the adjacencies. So this technology is at arm's length from sales engagement, from sales enablement, from marketing automation. And yet there's been very little partnering. I wouldn't talk about acquisition yet, but there's been very little partnering in the space along those lines. 

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James Kaikis: Why do you think that is?

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David Yockelson: I think people haven't thought through it. It's beginning to happen now, but that's gonna change where there's a closer link to those other key elements of the tech stack and where the sellers live, if it's sellers, and where the workers live, if it's marketers. 

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James Kaikis: I'm happy to hear you say that and I want to dig in there a little bit more. Where do you think the most probable partnership comes from with this space? 

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David Yockelson: I tend to always think on the CRM/sales engagement side. So I mean, I can make a good case for the Gongs and Outreaches and so on. I can make a good case for Salesforce or HubSpot or take your pick. And in a couple of different veins. One is if we're managing an opportunity through Salesforce or you're running a play or workflow from HubSpot or Outreach, showing a demo should well be part of that or making sure that it happened at the right time or teeing it off is one side of it. The other side of it is the data that the demos collect. So we talked about signals. Somebody traipsing through not one but two but three tours or having taken it however is fantastic signal data and so bringing that data back as part of that flow is huge. 

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James Kaikis: Thanks for sharing that. I would say from my opinion if I look at like the Gongs, the Outreaches and the companies that you mentioned, I think it's very interesting that these companies are doing like forecasting and predictive intelligence, but they're not bringing in POC analytics, right? They're not bringing in demo analytics. So like, don't those things have some sort of weight? 

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David Yockelson: I think it's a visibility challenge. So there are products that serve the SE world, and there are products that serve the sales world, and probably as you know better than I do, despite the fact that we love our SEs, and they're downtrodden and overworked and whatever. Does the CRO really want to make the investment in tech? Anyway, so I think that's one challenge. The second is that the sales tech stack is so ginormous and confusing that I think that there's probably a reticence to add another thing to it. The reason why I think they should is that it's the efficacy of the technology. Every day I encounter examples where, listen, we shrank the sales cycle by a third. We converted MQLs at a rate 5X what it was before. So the data is there and it's proven itself. 

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James Kaikis: Yeah, we actually have a use case with a customer running live POCs and they've taken POCs from 60 days down to two days and it's like, yeah, that's the thing that got the sales leader's attention. 

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David Yockelson: Oh, and not only that, but depending upon the product, it's, hey, we don't have to run end versions of the production product on my cloud. You spend a gazillion dollars a year doing that. Whoa, hello. 

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James Kaikis: For us too, the number of times we've heard that like CRO can't give demos or is like showcasing their own production environment and that's how this initiative starts is quite baffling and I think a big thing for us is, you know, we've talked to some people like, oh yeah, we're demoing production. It's like those are, you're breaking security, privacy, SOC2, like you shouldn't be doing that so. 

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David Yockelson: In a former life, I was in the video content management distribution space. And the leading buying occasion was the CEO is doing an ego cast and it fails. And he's like, you're all fired unless you fix this now. And it's the same. So now I'm ginormous company X or startup company X and now I'm doing the demo to my prospect and the internet's bad in the hotel or whatever or the thing is down. You can't afford to chance that. 

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James Kaikis: No, you can't. And I've got a saying and a feeling generally is that every time you're talking to a customer, you have to be delivering value. I feel like the pressure is on in every single interaction. And you got to be able to showcase a product that tells an inspirational story. You've got to have a point of view. And I think this is where all these shifts and go-to-market are actually happening. 

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David Yockelson: So one of the ways, and it's kind of a PLG thing and a demo thing both. This is about showing the value, literally showing the value. And from a sales perspective, you wanna have the value shown or show the value. It's passive or active, and then explain the value, talk about the value. And that's where they would earn their super commissions.

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James Kaikis: Yeah, and it's always like, I reflect back to my own career, like telling people to “imagine this” right? Or, you know, and it's like, what you see on the screen is different than what you're hearing and it's just not a great overall experience. I really want to thank you for your time today. It's been great getting to know you and hearing your perspective and thanks for everything that you're doing on the education and the category. 

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David Yockelson: Happy to be a cheerleader and helper.