SaaS Demo Best Practices: How to Crush Your Next Demo Call

Nailing the SaaS demo every time. Is that really possible? We’re going to hear from an expert in this episode of Closing Time. Thanks for tuning in to Closing Time, The show for Go to Market Leaders. I’m Dave Osborne, Chief Sales Officer at Insightly CRM. And today, I’m joined by Chris Orlob, formerly of Gong, co-founder of pclub. That I know and Quota Signal. Welcome to the show, Chris. I’m super happy to be here. And I got to be honest, I’m tempted to bring us back to like the conversation we were just having about me trying to prospect you like eight or nine years ago. I don’t know, man.. I almost think we should. So before we kicked off, I was like,. Man, Chris, you look so familiar. Like, have we met? And I’ll actually, I’ll let you take it from here. It’s kind of this weird small world moment that brought us together. Yeah, well. For everybody listening, So both Dave and I joined on the prep call, and we’re like, Do we know each other? Like, your name is so familiar? And he said the same thing to me. And he’s like, Well, I worked at Qualtrics in Provo, Utah for a while, and I used to work at Insidesales.com and was like, It’s more than that, though. And so I go into our. LinkedIn messaging history and I sent him a message in 2014 trying to prospect him while I was a sales leader at Qualtrics, when I was starting my first company, which was called Conversature, which eventually led me to Gong, so here we are, what, nine years later? Yeah, nine years. We finally got the meeting. Was it the meeting that we were hoping for? But, you know, perseverance. I’ve always been better at attracting prospects than going outbound to them anyway. So this is just another example of that play. That’s it, man. Well, I’m glad we finally we finally made it happen. A decade in the making. We finally got the meeting. But want to dig in a little bit about your what you’ve been doing since 2014. So, obviously, you had a long and successful tenure at Gong. You know, helping that company grow from I believe the numbers were astronomical, right? It was something like $200,000 in revenue to 200 million revenue. So. Super impressive run. Hard to argue against those numbers, right? I would love to dig in and talk about, you know, how you did it, you know, focusing on the all important demo. Right. Like how critical was that event in kind of the growth at that business? I think the demo is probably we can argue about this for a while. I would argue it’s the second most important piece of like predictable. SaaS selling. I think everybody would probably agree that discovery is first because you can’t really demo very effectively if you don’t do discovery. But you can also argue that the point of discovery among other things, is so that you can deliver a crisp, tailored demo that proves that you can solve your customers problem. When I compare how we did demos to how most SaaS sales organizations did them, they were very product centric, right? They were making the product the hero of the story. Whereas like we only demoed things in the context of solving problems that the customer had already shared with us. I know it kind of sounds cliche. Everybody talks about like the hero’s journey right now, but making the customer the center of the story in the demo is just kind of the tool in their tool belt to help them achieve a desired outcome and alleviate existing pain. So that was probably one of the first big ones. And then the second thing we did really well, we had this philosophy called Solve Exactly. Which is the cheesy analogy we would use is you would often hear like sales reps and other companies selling to a bank and the sales rep would be like, Now if you were a hospital, this would be really valuable. And then he or she would like go through a laundry list of cool features that would be relevant for a hospital but not a bank. It’s like, why the hell are you showing that anyway? And so our philosophy is we use our demo to solve our customer’s problem on a 1 to 1 basis, no more, no less. And unless there’s a good reason to, we don’t show parts of our product that don’t solve a problem that they’ve already talked about. Now there are a lot of exceptions to that rule. Sometimes you have to show parts of your product that don’t solve a problem directly because they give context to the parts of your product that do. But so many sales reps do like a Full Harbor tour thinking that if they show everything, it builds higher perceived value and all it does is deteriorates and destroys value. So those are a couple of things that we did really well. I mean, the makes a lot of sense and as you think about what we’re going to present, right, I’ve heard one of your tips is to show the most powerful feature first. Right. Which seems intuitive, but I’ve seen a lot of reps maybe borrow from the entertainment industry to the movie industry, where they’re saving the most impact for the climax at the end at the at the end of the demo, right? I mean, do you think that’s backwards or would love your perspective on that? I think it’s backwards because the only time you can pull that off, where you save the best for last is if you are a world class screenwriter and most account executives do not have the skills to be able to do that, where they’re creating open loops and coming back and closing them and creating more open loops like forget about it. Like you’re not going to get to the point of being able to do that well. And so the way we approach demos is based on the most painful thing we heard the customer share. We would show the thing first that solves that big, painful problem, like right out of the gate. There’s no mystery to this. Here it is. And we will unravel and unpack to the rest of the demo to whatever detail that you want. And so that works really well from the, You know, the well-worn principle that first impressions matter. The second reason it works is you can peel back to the detail that your customer wants, not to the detail that you think they want, right? Sometimes all you have to do is show that first thing. They’re like, That’s it. That’s all I needed. And some people will guide you and ask you a bunch of questions and they’re far more detail oriented. And then the last reason it works is, if you’ve got a group demo going and they invite the executive to it and you save the best thing for last. That executive might not be in the room anymore. If you got 45 minutes and you’ve bored them for the first 30 minutes and they’re busy, you’ve missed your opportunity. So if you’ve got high value people in the room, solve their problem immediately. And if you have extraneous things to talk about after that, save that for the second half of the conversation. Yeah, it’s a great point. And maybe just to take a step back, you talked about discovery and I mean, we’re talking about demos today, but I don’t think you can have a great demo without a thorough discovery, would love just maybe a thirty second like overview. I know it’s a big topic. We could spend a whole session on it, but your approach to discovery, right? Like and I imagine that differs a little bit if it’s an enterprise motion versus more of a commercial motion. But I would love to hear a little bit, just like I said, the the 30,000 foot view of your approach to discovery. Yeah, there are a few techniques that I think about that I use pretty consistently. The first one is what I call peeling back the onion or understanding the need behind the need. Right? Usually when you’re talking to a new customer, you can ask the most concise discovery question to start as you possibly can, but they still give you surface level answers. And they’re not doing that because they’re trying to like give you smoke and mirrors. It’s just they’re still articulating and crystallizing the problem in their mind. And so like the example that I often use, is I had a discovery call or me and one of my reps had a discovery call at Gong years ago, and we said, Help us understand what motivated you to come look at Gong. And we had an enablement person in the room and we got the SVP of Sales and the enablement person took over the conversation and he said, We need more visibility into our sales calls. So when you think about that language, we need more visibility into our sales calls. That’s not a problem. It’s a solution, right? We need more visibility. So we asked them what’s driving you to crave that visibility? And he said, well, we’re not very good at selling to power right now. We’re really struggling with that. So now we’re starting to get somewhere. But it felt a little bit tactical, so we peeling a little bit more. And what he ended up sharing with us was a lack of ability to sell to power is creating longer sales cycles than we had anticipated. Right? Our sales cycles are nine months and they should be six months, right? We build our annual operating model such that they’re six months, but we didn’t stop there. Like now we’re at a problem, but it’s still kind of a small problem. And so without being obnoxious, we were like, Look, I got the intrinsic value of you wanting to reduce sales cycles and sell to power better, but you’ve probably got 100 things you should be focusing on. So what’s going on in the business that’s driving energy toward solving this? And notice now that power took over the conversation. She chimed in, the CRO or SVP of Sales, and she goes, The reason this is so important right now is it’s causing a cash flow issue for our company, right? Our sales cycles are nine months. It takes us on average 60 days to even collect payment when we close the deal. And so from the time we begin a sales cycle to the time the cash hits the bank, that’s an 11 month gap. And of course, we continue this train of peeling back. And it turned out that if they didn’t solve this, they were going to have to go raise money in a bridge round or possibly even a down round because they’re raising money to solve a cash crunch rather than accelerate their business. Those are very different fundraising situations. And so when you think of, like the spectrum of willingness to pay along that conversation, the first surface level, what we got was we need visibility in sales calls. If you stop there, that is a deal that is just dying to go dark on us. There’s no way that thing is coming back to life. We’ve all seen that movie before for sure. You could see that coming. Now, if we stopped at like, you know, we need to sell better to power because we’re struggling with a long sales cycle, we might get a deal out of it, but it’s probably like, you know, a mid-size deal that we expand later. But when you really press and this is a skill because you can’t be obnoxious about continuing to press, but when we really continue pressing and we found out that the real problem is they can lose millions worth of valuation in their company at that point, price doesn’t matter, at least as long as you differentiate from the competition, Right? They’ll spend $500,000 or maybe even more to solve that problem. So that’s like the, I have others, but that’s like the if there was ever a magic bullet to selling, which there’s not. This is probably it. No, I mean, look, I think it’s great advice I’m sure in deal reviews or when you looking at win loss reports. I got to imagine that exact scenario, taking that superficial based pain and just running with it. Like that’s where I mean, you’re right. That’s asking for things to go dark. So sellers out there, if you’re having a lot of problem of your people going dark on you, I mean, that’s a good lens to how we start doing it, right? Is you maybe doing a decent job framing the problem, but you haven’t qualified it or validated it to a certain degree where you can actually wrap your hands around it and make a real good, strong business case. That’s right. So we got the discovery down. Another thing that I’ve seen happen quite a bit, right, is that sellers are so used to looking at their own app or their own software all the time that they neglect that the other person, the buyer has no idea what they’re looking at when you start sharing your screen, you just jump right in and you’re doing a demo and there’s really no context, right? So I’ve heard you suggest that a quick orientation is best way to start. So I’d love to kind of see how like what your process is to tee that up. Yeah. So I teach a demo framework called favorite. It’s an acronym and it is how you demo like each individual capability. In other words, it’s not like the full blown demo call structure. You would repeat this favorite acronym several times throughout a call, but after you’ve done a few a little bit of teeing up, like framing the pain, asking a question, getting them to visualize the value,. Now we hit O, in the favorite acronym, which stands for Orient them to the screen. And it’s really tactical, right? Like it’s not like this big sexy silver bullet demo feature, but it’s exactly what you just said. Like most SaaS sellers have the curse of knowledge. They eat, breath, sleep their products and their buyer is seeing it for the first time. And so they start clicking around on all these like, colorful charts with lines going everywhere, thinking they’re solving their buyers problem and the buyer the entire time is like,. What the hell am I even looking at? And so one of the best things you can do to just communicate more clearly how you solve the problem is take 30 seconds before each like key feature you show and just get them oriented. It doesn’t have to be more than 20 seconds, but say something like before I show you exactly how this works and how we solve the challenge you just shared with me. Let me just make sure you know what you’re looking at here. So over here on the left, this chart does. Y over here on the right, this graph does X, Y, Z,. Are you with me? And they’ll let you know if they’re confused. Usually they’re not by that point, you go, Great. Let me show you how this solves your problem. Right. It’s like just these simple little steps. It’s the little things. Yeah. Yeah, it’s the little things. I think of, like, Rome isn’t built in a day.. It’s just these little tactics that if you leverage, I mean, it’s like all that adds up together to making a really crisp presentation. Now, another tip you call out, or I’ve heard you say before, is spending tens, which I think is somewhat related to this. Right. Which is kind of how you balance presenting feature functionality with the pain or the business case that it’s solving. So would love to hear, you know, what spending tens means to you and how you deploy that. Well, I think what we’re talking about here is making demos interactive. And so there’s a few ways to do that. Like before you start jumping into a feature, the first thing that’s going through your buyer’s head is, what problem does the solve? If the buyer’s asking that, then you’ve probably failed at that piece of the demo. And so you should spend 10 seconds and it doesn’t have to be more than that before each piece you demo. Just quickly reframing the pain that that capability solves. So if you’re showing a piece of Insightly and you’re about to show a new like dashboard or something like that, and you say one of the things that you shared with me on our last call was X where X is like, you know, a small pain point. I mean, it could be a big pain point, any pain point, frankly. And you say, to what extent is that a challenge for you or something like that? You ask a question to get them to expand upon it and then you go into solving by showing the demo, right? You orient them to the screen, like I mentioned, you show how the workflow works and then you zoom out and you have a little bit of a conversation. Before you move on to the next thing you say, Talk to me about how that compares to how you’re doing it today and you get them talking to you. So there’s a rhythm to demos, right? There’s an ebb and flow of moving between features. You’re constantly framing the pain, asking your question, orienting them to the screen, solving by doing the demo, and then getting their feedback, getting a response, and then you repeat that 3 to 5 times, depending on how long your demo call is. I love that. I mean, I think orientation is critical on any demo, But I mean, one of the things that I think some sellers encounter we talked about a little bit earlier is when you’re doing maybe a small demo, like to a few different evaluators versus a large presentation, maybe there’s ten executives in the room. And we’re doing a big demo. I mean, do you adjust your approach with spending tens or how do you contemplate, you know, demo ing to bigger groups versus smaller ones? Yeah, I think you have to get really good at facilitating group conversations. There is a skill of facilitating that most sales reps don’t have, for lack of a better word, like the swagger to execute on. Right? It’s almost like confidence. It’s almost like you’re a trainer in like a small group session and you’re pulling people in. And so there’s a bunch of things you can do to make demos more engaging. I think one of the first things, though, is how you set up the expectations for that call. Because you can go in, there’s five people on the call and one of the first things that you should consider saying is, we have five people here. All five of you have unique challenges, pains, needs and one of my biggest concerns about this meeting is addressing all of those individually. And so I think what we’re going to strive to do is we’re all going to shoot for a North Star today like something that commonly unites all of us in terms of our needs. We’re going to speak to that. And assuming this resonates, then we can break this out into one on one sessions as a follow up after that. So I think that’s the first thing is just expectation setting. The next is assuming you’ve had several conversations with somebody up to this point. Generally you’re not jumping into a group demo like on the first call of a sales cycle.. If you are my heart goes out to you. I’m sorry,. I can’t give you advice for that. Yes. But it’s to drive engagement for the group. The first thing you should be doing is you present one slide and it’s a “what we heard” Slide. It is, here’s what I’ve heard from my conversations so far. Right? I’ve talked to Dave. I’ve talked to Courtney and here’s what they’ve shared with me about the challenges they’re facing. Jeff, what’s your take on this? After you summarize it.. Or Sally, what’s your take on this? And just getting those different voices speaking so that they feel heard, but also so you can take some of the things they say and interweave it into the demo that’s to come. Great, great advice. And you know, something else that kind of popped in my head was when you’re having these big group demos, I think a great sign that this is going well is if all of a sudden that room like they’re talking to each other, right? And then you as a seller going on mute and they’re just they’re talking amongst themselves as if you’re not even there. It’s like, now we’ve actually got the wheels turning. Like this is starting to really resonate, you can tell. So as a seller, it’s like you should embrace those moments, put yourself on mute, start taking notes. But let’s let that play out as long as we can. Right? Exactly.. Yes. It’s a great buying sign. So we get to the end of the demo, right? would love to see kind of how you kind of tee up next steps, right? Like, how do we catalyze a decision moving forward out of this demo? Yeah, well, there’s a couple things. One of my favorite ways to end the demo is like, you want to save some time to have some, like, discussion at the end of the call. Like, hopefully it was happening throughout the demo in the way you just mentioned, right? They’re talking amongst themselves, but after you finish your demo, summarize the key points you covered because that draws people back into the moment with you.. It gets them to reengage. And then I like to ask them, talk to me about what excited you the most about what we’ve covered today? And I’ll go around the room like,. I don’t want one voice dominating. I’ll say, Dave, what resonated with you the most or Courtney What excited you the most? And I’ll get them start to talking because what excited them the most can typically be mapped back to personal pain. Okay, So that’s one of the things. I’m going to do. The second thing is, once I’ve had that conversation,. I have zero data to back this up. A lot of people see me as like the data guy because I used to analyze like Gong data and say, Here’s what the best salespeople do. I have no data to back this one up, but I’m pretty sure it’s true just based on like my own anecdotal observations, the best salespeople that I’ve witnessed have a very strong point of view at all times about what should be done at the end of the call, what next step that they’re going to recommend. Right. And they’re not like overbearing about it, but they they never lack for a point of view. And the reason for that is selling, if you think about it, it’s an act of leadership. So if you’re a salesperson, you’ve worked at your company for a couple of years, you have probably sold your product on the low end dozens of times on the high end, probably hundreds of times. And so you’ve seen this movie a lot. And then if you think about your buyer, this is probably the first time they’re buying your product or if they’re like a repeat buyer, maybe the second. But like knowing that’s the context, who should be leading who in that situation? And yet you will often see salespeople end their demos on a whimper, not knowing what to do next. They’re like, they’re totally looking at the customer. They’re like,. What do you think we should do? Now, I want to be clear about one more thing. It’s okay to ask your customer’s opinion on what you think you should do next, but you should still have a point of view at the ready. Right? Like I think the best salespeople end their calls with something like this. Look,. I have a pretty strong point of view on what we should do next, before I offer my point of view. You know your organization better than I do. Do you have any strong opinions? Now, most of the time they’re going to say no. Like, I would love to hear yours. And when that time comes, there are three things that you should be clear about. What is the next step you’re going to recommend? And we’ve already been talking about that. Why are you recommending that next step? In case there’s like any pushback or you need to justify it. And then, who should be involved? Can you get prescriptive about what blend of people should be involved in the next step on their end? And are there other people on your end that should also be clear on the next or involved in the next step? If you can answer those three questions at the end of every call, you are poised to lead your customers to a successful outcome. Chris, couldn’t agree more. Well, thanks so much for these tips. This has been super enlightening, really great advice that hopefully sellers out there, whether they’re just getting started in their career or have been doing it for a long time, experienced people, can take and put it into practice in their own sales cycles but that’s all the time we have for this episode. Chris, really appreciate you coming on the show. Yeah, this was super fun.. Thanks for inviting me, Dave. And thanks to everyone out there for watching. We’ll see you next time on Closing Time.