The New Era of Sales Enablement: Content When Reps Need It Most

[00:00:00] Hey, it's Andrew here. Just quickly before we start the episode, I want to tell you about one of my favorite newsletters. It's called Strategy of Security. If you want to understand the companies, ideas and trends shaping cybersecurity and its sub-markets, you should take a look. Cole Gromos runs the newsletter and he has spent the last 20 years in cybersecurity, including stints at PwC and Momentum Cyber, the investment bank dedicated to cybersecurity. Recent articles I'd like include,

[00:00:30] how could platformization work in cybersecurity where he talks about there being lots of single vendor platforms, but not a multi-estate platform. And also one called demystifying cybersecurity's public companies, where he explores the pure play ones and also hybrid companies, which are in cyber. He lists all of them and then breaks down the numbers in all sorts of different ways. Now this is not a paid promotion. I just simply enjoy what Cole is publishing. Check it out at Strategy of Security.

[00:01:00] Strategy of Security.com. Now on with this episode. The Cybr Donut sales team needs to sell better. These execute better. They need to use the playbook and do their jobs. So says Bill Wallace, its CEO, in a moment of frustration. But where do you start? How do you assess where's the best place to get going? And how can the sales team use a modern approach to sales enablement to get better?

[00:01:25] These are big questions for cyber. These are big questions for cyber donut that many are facing out there right now, which is why I'm glad to welcome Ron Baden to the podcast. Ron is the head of sales at GTM Buddy. He's a many-time sales leader and a two-time executive at a sales enablement software company. In this episode, he gives candid practical advice. And this is the cybersecurity go-to-market podcast where we tackle the question,

[00:01:52] how can cyber donut get to 10 million in ARR by the end of 2025?

[00:02:08] All right. Well, Ron, welcome to the cyber go-to-market podcast. Now we are on a mission here on the podcast. We're trying to save a cyber donut. If it doesn't get to 10 million in ARR by the end of this year, they're going to close the thing down because there's no funding going forward. So the CEO is feeling the pressure. And, you know, he's done a lot of good things over the last six months to be running this series is bringing in more advisors to help him figure things out.

[00:02:37] And what he's realized recently is that they've invested in a playbook. I helped them create their sales playbook and train the team up and use a lot of things in it. But he's going to stretch his head a little bit because as he goes on calls, he doesn't see the team following the playbook. And he starts seeing pretty lax discovery, slightly different ways to position the company, different ways to handle objections.

[00:03:03] And he's kind of tearing his hair a little bit saying, well, I thought we could have given them all this. How come they're not using it? So we're here today to help the CEO fix the problem that he's seeing out there. So you're back around long time in sales, obviously. And you spent now two stints at companies that have enabled enablement teams.

[00:03:25] You know, you've gone in two different companies now and helped enable teams get that force multiplier so they can be more successful with the team. So let's bring that experience to bear. If you were to sit down with the CEO, what would be the first kind of things, areas that you want to have a discussion with him about how he should be thinking about fixing this execution problem? Yeah, yeah. So actually, I looked at the numbers and the numbers really interesting.

[00:03:53] I mean, almost in every category, they're doing great. Like this is a company that should be, is growing well. The reach from 3 million to 10 million in one year after the biggest quarter was a million. It's a big stretch. And especially with five reps. So conversion rates are getting better. But with five reps and trying to do it now, avoiding like building more pipeline and avoiding like the ramp issue, assuming we can only do it with the five reps.

[00:04:23] A greater than 300K a quarter quota is a stretch. And so the few things that I would start with are 100%. Let's get rid of the amount of work that they have to do that's keeping them from selling. So the non-selling work. So things like getting ready to prep for the calls and doing the prep that makes the call like successful.

[00:04:48] So first thing that I would focus on is right at the beginning of these discovery calls, enforcing and reinforcing the playbook at the moment that they're going to do the call. So for us, for what I've always taught, if it's a 30-minute discovery call, we want to do a few minutes of rapport building but focusing on business rapport. So you've got to give them business rapport things to think about. Then active listening. So build that skill set around an active listening.

[00:05:16] So that would be like a role play scenario where you teach them how to like you're doing right now. Very good active listening. Then reiterate the problems that we're trying to solve because a lot of software companies try to get into second, third world problems that they think their software solves. I read one recently, Andrew, where they had like first world problem was this. Second problem was this. And eventually they could like launch rockets like Blue Origin or SpaceX. And I was like, I don't know how software does that.

[00:05:44] But I guess fifth level, you could do it. So again, reiterating the problems that you can actually solve and then sort of filling in the gap. So like in a normal discovery call, if you're going to do it well and increase these conversion rates from 36% to what you need about 50% to get to these numbers is reinforcing that just-in-time delivery at the moment they're going to the call.

[00:06:10] Because we know if we leave reps to prep on their own, they're just going to repeat the same things they've always done that they think work, not work on, am I going to get better? So that would be the first thing is make sure that not only like deliver the right content, deliver it in a mode that they can use it, but then record them and score them on how well did they do in the game film to know on the skills matrix where we're falling down.

[00:06:38] That easily gets us from 36 to 50 right there. And that's something that, you know, I think we've all seen a lot of, right? Sales is a funny thing in that we learn something new and very quickly we have to put it in live fire environment in front of a prospect. And sometimes, you know, the time gap isn't very long. So it's almost like, okay, well, I got a call tomorrow. You better start using this stuff that I just gave you. And what people sometimes forget is sellers are humans, right?

[00:07:07] We have to get the chance to absorb and understand and learn and use and all the rest of it. And there seems to be that disconnect between, okay, we're asking you to change how you do things, but we're going to immediately put you in a pressure-filled environment and expect you to somehow just go straight to the new way. And, you know, human nature is such that that doesn't happen. You fall back to what you already know very quickly. So you're talking about just in time, in the moment. Give me an example of what that might look like.

[00:07:37] Yeah. So it's funny, Andrew. So the NFL, college football has had to adapt to this exact same problem. 20 years ago, the NFL said we have a scoring problem in the league. And when they looked at what was wrong with it, it actually was the time it was taking for a coach to run a play into the huddle. Like I had to hand it to somebody, walk them out there. That took 40 seconds. And so what they did is they put these helmets that had speakers in them.

[00:08:04] And lo and behold, the coaches could talk to the player right before they were about to go to the line of skirmish and right before the snap. And scoring, forget scoring for a second. They've added 7,000 more offensive plays a season by just eliminating running the person back and forth. 7,000? Holy moly. Yeah. Went from 29,000 to 36,000 20 years by doing the only thing. So in college football, they held up the signs.

[00:08:33] In pro football, they talked to them as they get to the line of scrimmage. So imagine you're now a quarterback and you get the play, but they've got all this information. And you're standing there and they're telling you, look at this linebacker. Look at this cornerback. Look at these things. Right? Now, you are prepped. You have all that just-in-time information. But in sales, we're still relying on them doing the research beforehand. We're relying on them remembering it. Well, what is our natural DNA and our behavior that we're going to do? We're going to fall back to what we remember.

[00:09:03] And that doesn't work because the prospects are smarter and they're adapting based on everything they speak to. So we need to give them literal just-in-time to the point where somebody's asking the question. The days of saying, hey, Andrew, let me get back to you or let me bring a pre-sales person or let me bring my manager. Like having a nine-legged sales call or a 10-legged sales call. Those days are over.

[00:09:29] And if you want to get ghosted instantly, don't know an answer to an easy question because our prospects, they want these folks to have answers right away. So the whole concept of these co-pilots, the ability to be on the phone with them, be on the call with them, and have the ability to answer these. Tell me about something business report I can share with them. Give me the answer to what they're asking right at that moment.

[00:09:56] You know, giving the answer because the prospect can find almost everything about what we do without having to talk to us anymore, sadly. And so our job is to fill in the gaps of answers they can't get. So we have to be very smart. All right, Ron, let's get to know a little bit more about you personally. I've actually got 49 questions on my list here. The good news is, Ron, I'm not going to ask you 49.

[00:10:23] I've got this advanced and it's encrypted algorithm that's going to do a completely random pick of questions from 1 to 49. And we're going to challenge you with the questions it comes up with. So first of all, let me just spin this wheel right here. Okay. I hope they're easy. All right. The first one is number 25. Ron, how did you first make money as a kid?

[00:10:53] All right. So I was always very entrepreneurial. So as a young kid, as a paper boy, grew up in Connecticut, cold, cold weather. I was up early Sunday mornings packing newspapers, rubber band, delivered them on my bike. My most famous person I delivered to was Gilda Radner and Gene Wilder. They're living up there. They lived right behind me. And I actually, he tapped me with his car and stopped sign one time. So that was my entree to try and make money.

[00:11:22] I was a little bit older. I started a small company called Sons for Sale. We did everything that parents wanted their kids to do, but they wouldn't. And so we babysat, cleaned, did yards, did all that stuff. So I would say really entrepreneurial stuff. Sons for Sale. Now, in this day and age, that's not probably a PC way to describe what you did, right? No. We also did it by mailbox. We did flyers and mailboxes, which also wouldn't work today. But we went and stuffed mailboxes. That's awesome. All right. Next question. Let me spin the wheel.

[00:11:57] Number two. What's an embarrassing or memorable moment in your work career you want to share with us today? Yeah, I would say there's, let's see, probably two. One, there was a quarter where I had the biggest deal at the company and we were heading to SCO. And I was trying to slow roll signing the deal to announce it at kickoff. And in the time between when they agreed to sign and when we went to kickoff, they paused all projects.

[00:12:23] And so that was super embarrassing, standing up to announce to the CEO that we didn't close it. So that was probably the most embarrassing. Let's see. A memorable moment, I would say. Very first deal, I won. The guy took me to lunch and he said, I just want you to know you were the worst salesperson I worked with out of everyone. And I said, well, why are you taking me to lunch then? He said, well, I wanted to give you this personally. And he handed me the contract over lunch. And I got back to the office and I was despondent.

[00:12:53] And my CRO said, why are you so upset? And so I got this stupid contract, but I was the worst salesperson out of everybody. And he reminded me I was the worst, but the only one who got the contract. So it was a great and memorable moment for me. Yeah. Both of those funny stories. I can't imagine the first one where you think you're being quite smart to pull out the contract at the right time. Yeah. For you want to ever hear the worst story about time kills deals. That was my example of time definitely killed my deal.

[00:13:22] Oh, boy. All right. Let's spin this wheel for the last time and see what we get. All right. Number 47. What is the story behind you getting your first job in enablement or sales? Yeah. God. So enablement. I'll start with an enablement one. I didn't even know that we were doing enablement because back then it wasn't called enablement.

[00:13:52] It was just called training. But I was asked to write a sales play on how to do a discovery call. And I grimaced about it and just was absolutely miserable about it. And when I realized quickly, I did it and was like, this is no value. I'd rather just teach a class or be in deals with raps. But I learned that by writing that one play, I was actually influencing like thousands of hours of sales calls. And so I don't think it was my first moment in enablement.

[00:14:20] It was the first one I realized there was some version of a force multiplier and a way to really scale and not have me physically be in every deal, but actually get me as a part of me into every deal. So that's probably the memory of where I've said, yeah, enablement is a huge way to scale in an organization when you can't just hire people.

[00:14:45] And what's changed then in, I don't know, technology or the sales landscape that allows us now to do that as opposed to 10, 15 years ago where if you talked about, you know, in the moment stuff, people look at you cross-eyed going, I have no idea how you flash a card in front of someone's face. Yeah, well, so there's one thing you don't do, and I'm a firm believer of this. So you don't have someone in your ear like being in – I was on the radio for a few years in my earlier, earlier, earlier years.

[00:15:13] And one of the things that stopped me from doing was having the earpiece in my ear and having someone talk to me. I could not have a conversation. Like it just really steered me the wrong way because I would worry about what they were saying and not the conversation I was having. So I'm an anti-co-pilot person. I love the idea of delivering content in real time and delivering it to people. But imagine a quarterback who's on the field and they're in the play and they're about to throw and make this amazing touchdown throw and someone goes, no, don't do it.

[00:15:43] Go right long. Exactly. 83 is open. It won't work. So we don't want to do that with our reps either. If the reps already know the answer or they know what they're doing, like this is the science. So what we expect – so the CEO, Cyber Donut, what they expect is I'm going to give them a beaker. I'm going to add a few ingredients and I'm expecting a chemical reaction. That's the science of sales. And that's what we have to make sure we do.

[00:16:08] Now, the art of sales is adding in that little wiggle, the little wrinkle once the play works. Like we have a running back. We give them the ball. They run three yards. If they've got daylight, we don't tell them to take a knee so we can run the next play. We tell them to run to the end zone and score a touchdown. Same in sales. We don't often give them the outcome of who we want the play to be. So we don't know if it really works.

[00:16:32] But I think the biggest thing right now is delivering just-in-time enablement in the workflows they work in. So if I'm running a discovery call, I run it from my calendar because I'm running from call to call. I need the prep. I need the ingredients to make that chemical reaction happen. By the way, I don't want to blow my fingers off. I don't want to blow my eyebrows off. So I need to do it right. But what is that chemical reaction? And how do you get it from the CRO who knows it? Because they know what the company does.

[00:17:00] They know the answer of why they solve it. They've built the company. How do you scale that and get it to everyone? And that truly is where now these just-in-time enablement products can deliver it in their workflow. So if you're in the inbox, send the right content. If you're on a calendar running a disco call, have all the answers right at your fingertips. And then give us the ability to understand how I can get an answer in real time.

[00:17:28] So an agent that's product-related, an agent that's customer name-related, where I can just go in and ask a question. Because truly, my prospects are a prospect. They don't want content. They want answers. Reps don't want content. They want answers. And so that's really one of the big things we have to change. Let's not give them a 15-page doc that has everything in it. Let's just give them the answer when they need it, but not distracting. So let me kind of drill into that then.

[00:17:55] So the experience as a rep, I'm on the call and try to remember my best disco questions. I'm trying to remember what I was taught last week. Am I looking at something on the screen that kind of is my dashboard that says, okay, well, here's some good questions to ask given what's happened so far on the call. And then as you get the flow of the conversation, are things kind of surface? Is that what we're talking about? Yeah, exactly. Like I was telling someone this the other day, my wife said, let's go to a comedy show. And I said, I'm happy to go to a comedy show, but not improv.

[00:18:24] I don't like improv. Like it makes me nervous. Give, show me a script of a comedian that I know is going to be funny. That's done it before. They've gotten laughs from the jokes before. That's sales. Like why, why do we try to rewrite all of these things that have worked in sitcoms and comedy shows and plays? NFL coaches script their first 10 plays. There's no guessing on what they do. They know they work. It gives them information. So you mentioned discovery calls.

[00:18:51] Why not curate the best seven or eight questions that have been asked, that have gotten good responses on disco calls? Not where we had a 54%, 64% reject rate. But what did we ask people on those opportunities where we converted at 36%? What did they say? What were the answers? What was the good objection? And if I'm armed with those, I can change the trajectory of those calls really easily. Because I've got confidence in the question.

[00:19:21] I'm going to come across confident. I'm not going to make it sound like an inquisition. 100%. I'm going to make it sound like, you know, I'm interested in them solutioning. Because I know these are questions that people have answered and it's worked before. So in the workflow, being able to look at a script, a job aid that says, here's your business report. If it's a 30-minute disco call, science. Here's the five minutes of business report. Here's the 10 minutes of active listening. Here's the repeating of the questions.

[00:19:50] Seven minutes of a demo to just show the eyes what the brain heard at the beginning. Or the ears heard at the beginning. So yeah, a job aid in the workflow they work in. So that they've got that scientific equation right in front of them. And as a seller, as I'm trying to make this change and I'm thinking through what I'm listening to. How does the CEO build up the skill set so that person's thinking about the right things along the way as well?

[00:20:20] Like how do they make that change before? And you mentioned the word practice before. What's your recommendations around that? Yeah. I mean, so it's really funny because in sales, I mean, so let's talk about the two types of practices that teams have done historically. One, I'll give you a quiz. You read the playbook. You read ahead. You answer the questions. You get 60%. All of a sudden, we think you're trained. That's not what we do. If you think I'll go back to the sports analogy. They hand them the playbook. They quiz them.

[00:20:50] Then they walk it through with a position coach. Then they walk it through like running the play until they have it right. Then they simulate game. Then they bring in game fill. So first, we've got to get away from the idea that just giving them the playbook and asking them to read it is going to be the way that people learn. The second thing, Andrew, is truly role plays are an amazing idea. But all three parts of role playing are really hard for sales leaders and salespeople.

[00:21:17] The first part of creating the role play and executing it, it's just hard because how do we simulate all the scenarios of a dog barking? And somebody being upset and, you know, like I said this to someone the other day, my dog peed on the carpet and I became terrible at the role play because I was mad at the dog. All of a sudden, I was a mean seller. It was a brand new rep who didn't need a mean seller. They needed someone nice to them who was just going to do a five-minute role play. So it's really hard to simulate. Then it was hard to actually execute the role play because I had to learn it.

[00:21:47] And it's a lot of learning on what you're going to say about the products and competitors. You don't want to be too biased. But the worst part of it is I was running from call to call. It's at the very end. He said, how did I do? And I went, you did great. Keep it up. We'll talk later. Well, that's such garbage. Like what do they learn from that? You get an attaboy, right? Yeah, that was great. Exactly.

[00:22:09] So the idea of using the content, content being your competitor pages, your product pages, your calls that you've run, using those and leveraging AI like a five to run the role play. But only answer specific things. So like take the parts that you're struggling at. So let's say on this discovery call, what's driving us down to 36% is not identifying the problem or the pain or the impact of it.

[00:22:39] Let's just role play that. If that's the part, you know, like a lot of times we'll go, oh my God, you're so good at business report. But we end up role playing that 5,000 times. We never get to you stink at objection handling specifically around identifying the impact of a problem. How do we repeat that behavior? Because it's about changing their DNA to understand what the CEO knows to work. How do you convince them that this is going to have great success? That's the thing that reps reject on.

[00:23:08] If I don't know that it's a document Andrew's verified or I don't know that the playbook worked, I'm going to revert back to this is how I've always done it. So I think the two things that like would save Cyberdonut is enforcing the playbook, but reinforcing it because reps want, the reps I've worked with, they want three things out of their job. They want to make money. They're very coin operated. We all want to make appropriate money. They want to have fun, which is a cultural thing, but they want to learn.

[00:23:36] And if we're teaching them and they're learning, they will apply that learning. If not, they're going to fall back to the habits that have made them reps. And, you know, that's how you end up with 36% conversion rates. Now, one of the areas, Ron, I would imagine people listening to this, they've either maybe looked at AI role plays in the past or whatever, and they've got whatever experience they've had, right?

[00:24:00] You know, AI is the pace of innovation and getting better AI is incredible, right? So a bit of a skeptical question then. So, you know, how good truly is an AI role player these days? What's the acceptance rate, let's say, of a rep to say, you know, yeah, this is actually pretty good? Yeah. So it's getting better. Like even when I first started looking at them, and it's not about do they sound like a computer? Do they sound like a human?

[00:24:30] Those aren't the issues because who cares if you're talking to a computer, right? Like that doesn't matter. It's am I getting better as I'm doing this? So are they learning the objections? Are they learning the persona questions? And so I'll tell you a quick story. I was training a rep the other day. They were doing their first discovery call. And as we were on the call, we got a calendar update that a new person was added to the call. And as they were added to the call, we did a quick LinkedIn search. Turned out I was a CEO.

[00:24:56] And all of a sudden, this new rep was like, oh, my God, I prepped for a persona of X. How do I, within the next 45 minutes, learn to up level to a CEO? That's a great question, right? That is a very fair question. We built a role play. We very quickly just said, here's an avatar. Pick a CEO level person so we know it's going to keep it high level. They're going to be a little bit short. Their attention span is probably not going to be totally fixed. You can't ask them a billion questions.

[00:25:25] You got to get to end. You know they're in active buy mode. If they're spending time, they're coming into mode where they're buying something. And we did the role play. And frankly, the rep was terrible. First four or five times, the avatar, the AI rejected the questions. And it was just like, look, I'm a CEO. You're asking me low level questions. My team can answer that. But so we eventually got to a point where he did enough of them where he's like, wow, okay, I think I'm ready to handle that.

[00:25:53] When we got on the call, the CEO was actually impressed and said, as a new, because I told him, as a new rep, he's like, how did you get him here? I played the role plays. The first one and the last one to show how much better they've gotten. Here's the key to the role plays is you have to use real life game fill, real life scenarios to train it. So just like one of my favorite stories is that I'm not a Patriots fan, but the Patriots prepped the play where they beat the Seahawks.

[00:26:21] They'd run it a hundred times that slam play. They'd run it a hundred times. They knew exactly what was going to happen on that play. There was no surprises. Do we train our role plays to be run a hundred times or do we just run them once and then say, that's good enough? So you really have to invest in it to make it real life. And the only way to do that is to take calls, to take your battle cards, like real data.

[00:26:47] If you're rebuilding content, then rebuilding the role play, it doesn't look like that's the scenario. You're going to lose the rest. So make sure I understand that then. So what we could do is say, well, here are the last 15 CISO calls that the team had. Here's the transcript, you know, essentially from those calls. Feed that into the knowledge base for the role play engine. Now, let's imagine now we're having the 16th CISO and then 17th CISO call. Use those other ones as the basis for this. Is that what we're saying?

[00:27:16] That's exactly what we're saying. Yep. Even going backwards to that very first discovery call, how do you reinforce or enforce the right behavior? Why not before they get on the call, have them just redo a five minute role play of the section of it that they're not great at? So, hey, you're meeting with a CISO. They want to talk about these specific products. Brief yourself on them. Let's run it through. Let's hear the objections live.

[00:27:45] Let's practice it and hear the words. Just like we used to do back in the day, standing in front of the mirror, you know, trying to convince ourselves of, you know, how we would say stuff and how we would feel confident in it. Why not do it right before? Like this just in time job aid of being able to say, I'm meeting with a CISO. I know what that means. I know what their goals are. They're going to love if you come out and don't say, I like your shirt. I like your blah, blah, blah. How was your weekend? Instead, it's like, hey, I just solved this for someone else.

[00:28:14] Would you like to hear about how I solved it? Now you're their trusted advisor. Now they're going to answer your questions and you're going to get a much. And that's the thing. It's like think about how quickly we have to build rapport with so many people. It's not like a champion, multiple execs, sponsors, multiple champion, multiple people in a buyer group. We have to build a lot of rapport along the way. And we're losing that skill set because the prospects are demanding that it's business

[00:28:43] rapport, not personal rapport. You know, it's funny, right? As I hear you talk about this whole area and imagine where things were five or 10 years ago, in some ways, there's a parallel to cybersecurity where, you know, you're having to change people's minds about what's possible now that they didn't think was possible or had preconceived notions from and cyber as well. You know, a lot of these companies are bringing new ways to market to tackle all problems better in their opinion.

[00:29:08] I'm wondering what you've learned about how to go about changing that perception or changing people's minds that there might just be a better way to just listen to what we're talking about and how we're doing things. So there is because all along, like I believe, so first, I believe we've been doing enablement for a long time. The word enablement in our world today is now a function, just like customer success became a function.

[00:29:34] Do we actually believe that before we had a department called customer success that we didn't do customer success? No, everybody did, right? So who did enablement before the enablement department? I mean, everyone, the CEO, the CRO, sales leaders, even finance, would talk about how to write a good deal. And so the first thing we have to realize is that enablement is about creating a force that helps get these ideas to the reps to make them better.

[00:30:03] Win more deals, win more micro conversions, win more pipeline. It's not let's hire more people. So like in this example where we're trying to get 300K a quarter and our ASP is 120K, we need each rep to close three or four deals. And if they're only winning at a 60% rate, we need what, six deals, seven deals that they have to work on. We've got to be exacting. And so they want to do that. They want enablement.

[00:30:31] What they don't want is to just be told. So these can't be just telling events. They have to be actual selling events. Right. Yeah. It feels like that there's an element of seeing is believing as well with people. Right. They just, you know, OK, everyone promises the world. But what can you, you know, which part of which country can you actually deliver is the bit that people are kind of latched on to. Yeah. And I was so at the three things that we're seeing the big change in enablement are the,

[00:31:00] you know, giving time back to the rep. So instead of the reps having to go search for content, search for answers, they're presented with them. So that's the number one thing. Next is this whole conversion. How do we increase our conversion rates even to our micro conversion? And that's all around. So that's the segment. But the last way is, you know, these buyer groups today, like how do we get selling when we're not selling? So this whole concept of digital sales rooms.

[00:31:27] And by the way, people who've been doing fundraising have known about these digital rooms for years. It's how everybody did fundraising. Put all your data in there. We're going to look at it. We don't even have to ask you a question. We're going to come up with our own hypothesis. So what's the best way to convince our sellers that we're going to help them? It's not yet on enablement. It's a new way for them to get to people and sell when they're not selling.

[00:31:52] So a lot of the big pushes around digital sales rooms and allowing them to ask their own questions and allowing them to get their own answers. So we like to start there. It's kind of the end of the process because you wouldn't think that people would need content or answers early. They want it from the first day. After our first discovery meeting, the very first thing we do is we say, Andrew, we're going to set you up with a digital sales room and you'll be able to find answers and get your content without us.

[00:32:20] You don't need us for that. I can enable you to go do that on your own. Now, what do I want as a rep? I want insights. I want analytics. What are they looking for? What are they searching for? What answers are they getting? What answers do they need? And then I can arm my prospect with that. So my champion could be on selling while I'm not even selling, which is awesome. So that's the first thing. We just had a customer who did a contest and they had a rep close a deal in 28 days.

[00:32:49] It was a cybersecurity company, actually. The fastest deal they closed in company history. And it was all through the digital sales room. And that was what they were trying to do was drive behavior of forget about that. It's an LMS or CMS. Who cares? Those are the arrows in the quiver. How do you drive a behavior of shortening the sales cycle so you don't have to schedule a call and bring a person and do it in two weeks? Why can't they look at it today? And that's a big change.

[00:33:16] So that's the first way that you change their minds is just change the way that they interact with the old things they've been doing. So we used to send emails to people. I used to love this at the end of quarters. My manager would ask me, did you send the email? Yes. Did they look at it? I don't know. Then if he came to do send it, did they look at it? Yes. I don't ask my reps ever. Did they look at it? Did they look at the pricing page? I can actually see myself that they looked at the pricing page, how long they looked at it.

[00:33:45] And so if you give the reps something, then they're going to give you something in return. If all you're giving them is governance and compliance, they're not going to care about that. That doesn't make them money. Updating a field in Salesforce, it doesn't make them money. That's for the sales leader. Giving them an answer to a question to help them move a deal today versus waiting a week, that's what makes them more efficient and makes them more money. You mentioned other cybersecurity companies there.

[00:34:13] Have you seen anything unique about where cybersecurity vendors are getting results quickest inside GTM Buddy? Or is it the same really as everyone else? No, I think there are a couple of ways. So first, selling cybersecurity can be a very technical engagement, right? And you're selling to a CISO who's also not very trusting, right? I used to sell to finance in my career.

[00:34:38] And every time a CFO would come on the phone, we had to ask the company, are they CIF no or they CIF yes? And I think CISOs have a very similar reputation of just, I'm doubting you until, what's the very last thing we do in every deal? InfoSec, checking all your credibility, you know, all that stuff. And so imagine you can make that process faster. If you can make it more plain English.

[00:35:04] So if I could summarize a 15-page technical doc and I could tell my seller the three things in plain English they should say about it, well, now I've scaled them. Now I've made them way more educated. I don't have to hire someone who's a deep, dark technical expert and understands everything about what it's actually doing. We just have to explain what the process is and what it's going to solve. And so I think there is a big change in the fact that they're trying to hire and scale very quickly.

[00:35:32] Their businesses are growing incredibly fast. So, and you're dealing with a buyer that you really need to understand. They're a goalie, right? Like they're not, if this is a soccer match, I'll change boards. But they're a goalie and goalies aren't allowed to give up any goals. CISOs are not allowed to have any breaks, any problems. The data has to be protected. Password doesn't, like they have to be perfect. And so how do we convince them that with what we're doing, we can give them that level of perfection very hard.

[00:36:02] And so the just-in-time content, the ability to not to share content, but like worrying about their persona and building rapport with them. I think there are ways that we can build trust and we can change how fast we can get a rep ready to have these conversations. Yeah, it feels like there is some sort of break between the security operators, you know, practitioners and sales. There's even podcasts these days. Their whole premise is that relationship is broken. How do we go fix it, right?

[00:36:32] And whatever we can do as sellers to be more knowledgeable, be more relevant for people whoever we're meeting with, seems to me is there's a huge opportunity to make a difference. I'd love it. You know, think about a seller, Ron, in cyber, right? Most of the time, your entry point to an organization is middle management, director, whoever it might be, right? And then some of the time you might get to someone with an S or a V in their title.

[00:37:01] And then once in a while, through whatever networking or instructions or whatever it is, your entry point might be a CISO, right? That's pretty rare. If I've got my once every two months CISO meeting, I love it if I could set up a whole simulation about how I can do this call. And let's imagine he's in a good mood. Let's imagine he's in a bad mood. You know, let me play this out 15 times before I get on the phone with a guy and actually feel like I might know what I'm doing when I get there.

[00:37:28] And oh, by the way, let me play it out with the last 10 calls my entire team has done with CISOs or CISO, right? I don't want to just simulate it. I want to actually do it so that I'm prepped. I want to fail. I want to answer it poorly. But like, you know, people often ask me, like, how do I get into sales? And I'm like, well, tell me what you think sales is like. What do we think selling is all about?

[00:37:55] And, you know, in general, Andrew, it boils down to objection handling. Whoever the best objection handler is going to invariably get the sale. The ones who can know what the objection is before the objection even comes are the ones who are the great walls. So how do we get those objections that people can be prepared for, that they can handle themselves without sweating, without getting nervous, without saying, I'll talk to you tomorrow.

[00:38:22] Like if you get a chance with a CISO and it's a five minute conversation, you got to be good. You got to be prepared or that will be a two second conversation and it will be over. So how do we take that and get them ready? That's what content delivery is, right? It's not about content storage anymore. Everybody does content storage. And I learned this the hard way. So my wife and I downsized from a 4,000 square foot house to a 2,000 square foot condo. And my wife said, we're not getting rid of anything. So I got a storage shed.

[00:38:51] And you know what I've done three times in the last 12 months? I've unloaded it completely. Now, why we have my son's one year old flash costume, I don't know. But do I ever need to take that out? Do I? But so here's what I do. I take it all out. I find the two things I need. I put it all back. And now it's all in a different order of when I had it in the original. So if you think of storage, what's new in storage? It's nothing. But if we could organize it and I could instantly know where it was and I could get that content.

[00:39:21] Oh my God, my life would be dramatically different. That's what enablement has become for content. How do we give them that one piece of information that's going to make that one plate actually work in the moment they need it to work? So that's where we're at with enable. That's a strong position to be in, right? If we can help sellers be that good or have that at their fingertips when they're having these important conversations.

[00:39:48] Ron, we're going to have to reach the top of the hour here. We're going to have to end this probably shorter than I'd want to. I'm curious, though, as you think about all the interactions that you're involved in these days, is there one kind of non-obvious thing that you've just learned or something that goes against conventional wisdom as people kind of approach helping their salespeople get better? Is there something that you've realized that is very different to what everyone believes out there? Yeah.

[00:40:16] So I think there's this belief, and we've kind of all propagated it. I think there's this belief that AI is going to replace a lot of – AI is going to replace self. I think people have said that. There's been debates back and forth. I think there's art. There's enough art in what we do that the bots can't learn that I don't think that's going to happen. But I can't tell you how much people underestimate the amount of busy work we can take away from sellers.

[00:40:45] And frankly, I would solve that first. Like I'm learning there's about 40% of waste in the obvious things, updating the CRM, running deal reviews. So now I don't allow anyone to come to a deal review unless they've prepped and they have the answers. Like an AI is getting those answers.

[00:41:05] So that's where I would say like start with automating the redundant – like if you only have five sellers and you're trying to go from a million a quarter to two and a half million a quarter, you've got to build capacity, add capacity. Well, how do you do that? Take away crap no one wants to do, right? Like it's great to get the answers, but if you can get rid of some of the junk work, then you've created a lot more capacity.

[00:41:30] So how much time do we waste in prepping and then executing and saying the same things we always have? Let's automate the prep for it. But then let's practice. Bring in the game. So I think the biggest thing for me is just giving people back their time. Like how do we give them time to go do the things they're really good at? It feels like if you look at Cyberdonut, right? We've got what, five or six reps right now. The temptation might be, well, double that number to 10 to get the capacity.

[00:42:00] You know, when you add in new sellers, you increase the risk, right? You don't know if that person is going to work out. Even if you know them, you don't know in this environment if they're the right person. You obviously want them to and you want to help them. But until that person actually gets in the job and starts doing their magic, you just don't know. It would be much better to say let's invest in the five or six we have right now. Let's figure out that 40%. Let's take 10% away one quarter, the next 10% and increase our capacity with people that we know are already succeeding.

[00:42:29] We just need to give them more room to succeed more, right? It's a really interesting thought. Yeah. Think about it this way. Like if we'll go back to the football analogy, if you have a great wide receiver and you've just thrown the ball to them 10 times, you say, oh, that's enough. We're not going to, we're going to throw it to the person who's worse than you. No, but we do that all the time, right? And think about if we added a new person today and our normal ramp is six months, the reality is we're not getting any capacity until Q3.

[00:42:58] We're taking away valuable leads from people who could close them a higher rate. And all you have to do is eliminate the busy work. Like I did the math at 120K ASP. They've got to win three deals. If they're converting at 60%, they only have to work five deals. What if we converted higher? And where's the chance of converting higher? Training them more, getting them to a point. Now, there's obviously diminishing returns, but there are no diminishing returns of getting stuff off their calendar that's a lose, right?

[00:43:27] Like I read something the other day that if you're doing deal reviews, which is just a look back, you're wasting your time. We could summarize deal review using AI in a second. Why not do a go forward deal prep? Like that's a great use of time for a sales leader to be on a call with someone and say, here's how we're going to go win this call and let's practice it. We're not going to waste time reviewing it. And because like you've done this, how long does it take to a manager to swap into a deal? Where did the lead come from? Who was the last person you talked to?

[00:43:56] It takes 10 minutes to swap into every deal. Forget it. I already got all that stuff. Let me go forward and do the prep. And what I'm going to prep you for is how to go win that micro conversion, that section of a deal. I'm not worried about whether I win the deal. I need to win this stage of the deal. So eliminate all the nonsense, BWD40 and eliminate all the friction and the nonsense in the deal. We were on the phone yesterday with someone and they were looking at answering InfoSec at the end of a deal. They said, this is our biggest challenge.

[00:44:26] At the very end of a deal, we send stuff. It takes two to three weeks to get through InfoSec. And I was like, what's the bottleneck? They're like having it all in one place. We send it. Then they don't have all of it. They need more. We have to resend it. We don't know if they've read it. We don't know if we get it to the right person. That's an easy fix with a digital sale. In one second, you can fix that and be done. And they're like, wait, I can eliminate all that by doing one easy thing. Yep. And that's the world we're in today. You invest in the people that are there.

[00:44:53] Adding more people is not the answer anymore. It's an old way. And wisdom, the CEO is off pondering, what the heck? This could be an easy fix if I just cut my shit together and help my team in slightly different ways than I was thinking about. So thanks for joining us. If we had stock options and swag, I would send them to you as a thank you.

[00:45:22] But in the meantime, just a verbal thank you for what I can give you at the moment. But it's been fun having you on. It was awesome. Thanks for having me, Andrew. Good luck to Cyberdonut. It would mean a lot to me and to the continued growth of the show if you'd help get the word at.

[00:45:50] So how do you do that easily? There are two ways. Firstly, just simply send a link to a friend. Send a link to the show, to this episode. You can email it, text it, Slack it, whatever works for you and is easy for you. The second way is to leave a super quick rating. And sometimes that can seem complicated. So I've made it as easy for you as I can. You simply have to go to ratethispodcast.com slash cyber.

[00:46:17] That's ratethispodcast.com slash cyber. And it explains exactly how to do it. Either of these ways will take you less than 30 seconds to do. And it will mean the world to me. So thank you. Thank you.