Unlocking Business Value In Cybersecurity From a 25+ Year Cyber Sales Veteran

[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 company's ideas and trends shaping cybersecurity and its submarkets, 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.

[00:00:27] Recent articles I'd like include 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.

[00:00:57] Check it out at strategyofsecurity.com. Now, on with this episode.

[00:01:33] If things start flashing at me, I'm just going to start clicking them and hopefully it's going to fix whatever problems we have. If it feels like this is done by a beginner, it is done by a beginner. So give us a little bit of grace about it as we get through this. We're recording this on Friday, the 16th of May. If you're having to listen to the recording, it's a bright, sunny day here in Colorado. And as always, Cyber Donut needs some help. It needs some guidance.

[00:01:59] We're trying to get to that $10 million ARR by the end of the year. And it's time that we got the professionals in. We found someone who understands sales culture, who knows how to execute a sales go-to-market motion, knows about big deals, knows about selling value, collaborating internally, and is a thoughtful and insightful sales leader.

[00:02:22] Which is why I'm pleased to be joined today by Robert Amesqua, the SVP of Worldwide Sales at Forescat. Rob, welcome to the podcast. Thanks for having me. It sounds like a lot of pressure that's building on us here, but I'm glad all the buttons are on your side. So you've got more of the pressure than I do. Yeah, I don't know. I must be able to transfer them over, though. Delegate. That's what I need to do. Delegate some responsibility. That's over to you.

[00:02:52] Back up the question, how can Cyber Donut get to $10 million in ARR by the end of 2025? Firstly, I've got to thank Evan Dornbusch, who is a multi-time founder. He listens to the podcast. I met with him at RSA, and he said, you've got to do a live session. You've got to do one of these live things at some time. So I appreciate the encouragement from Evan to get this done. And also to Danny Wolf, who's the co-founder at Cyber Synapse, for putting me on to the software restream, which we're using to run this service.

[00:03:22] So thanks, Evan, and thanks, Danny, for the support and the tool to get this all done. But enough about me and the podcast. Let's go to Rob. Rob, let's learn a little bit more about you. As always, I have 49 questions here, believe it or not. And what we're going to do is actually spin the magic wheel.

[00:03:45] And this wheel uses advanced random number generators, which the algorithm is protected by ozempic encryption. It's not the full stuff. It's slightly lighter than usual. And there's no way it can be hacked. So whatever numbers come out, we're going to read the questions that these numbers correspond to. You ready to go? Let's give it a spin.

[00:04:13] Right there. OK, we've got number six, Rob. How did you make money as a kid? How did I make money as a kid? Oh, boy. Well, every which way possible. You know, I think I had quite a few lemonade stands. I think, you know, peddled some baseball cards, you know, mowed some lawns. Probably was the top seller at every single garage sale that we had in the neighborhood. And, you know, I was always looking for a deal.

[00:04:39] So that was pretty much my my early stage youth and probably my early days of learning to be a seller. And do you think about doing that as a career, starting a whole big business around Texas to do this? No, I walked around actually with that experience and realized that I didn't want to become a seller. I wanted to be a doctor instead.

[00:05:01] But thankful Baylor University weeded me out early and they robbed the world of a hell of a doctor, but gave a mediocre sales guy instead. So there you go. Yeah, you're a doctor of selling. That's what you became. All right. Let's go with number two. Number 38. What's an embarrassing or memorable moment in your sales career?

[00:05:27] Well, every loss I've ever taken, I can assure you, was an embarrassing moment for them. And there's quite a few of them. But, you know, and if you don't count my recent stay in a Chicago hotel where the drapes didn't quite close as far as I wanted. And there was a gym right across the street that could see through my windows. And you don't count that as an embarrassing moment.

[00:05:49] Then I would say that, you know, most of my embarrassing moments, thankfully, have been treated with grace and forgiveness. And most people have a short memory with respect to them. So I've been able to survive most all of them. You know, there's a story that's actually true. Denver Airport, I live in Denver. There's a Western Hotel at the Denver Airport. And this pilot stayed overnight, got up the next morning, getting dressed in his room.

[00:06:17] Didn't realize that the whatever it was, the neck curtains, not the floor or whatever. He actually got arrested. Someone complained that he was flashing from the window or something. He's standing there getting dressed. And it was actually a curtain, but not the full one. And it was all in the papers and everything here. So you got to be careful with these things. Someone will take offense to anything these days, it seems. Yeah. You know, when I had that episode in Chicago, I had flowers and bottles of wine delivered to my door afterwards. So I don't know what people saw, but I think they treated me a little differently.

[00:06:46] Was it the blind school up across the road or something? Is that what it was? I think it was. Yeah, it was. It was something like that. All right. Third question. Number 28. What is the story behind you getting into your first job in cybersecurity? Oh, great question.

[00:07:08] Well, I started out as a door-to-door telecom sales guy, which after about three months of doing that in a suit and tie in the sweltering Texas heat, I quickly realized that, number one, I was not very good at it. Number two, I wasn't very passionate about selling long distance door-to-door back then. And number three, my fingers were quite sore from getting all the doors slammed on them.

[00:07:37] And there was this little company called Network Associates that was starting up a Dallas-based office. And I'm still very thankful to this day for Tom Judd and Vince Kearns taking a chance on a young guy like me and basically giving me an opportunity when I went over there. And we went into this random building and these mass interviews. And I walked in there, and I had a pulse and a warm temperature and some shoes on my feet. And they basically said, you know what? Can you answer a phone? I said, yes, I can.

[00:08:05] And they said, do you know what a fax machine is? I said, no, but I can learn. And they said, well, OK. Well, do you know how to pick up POs? And I was like, I can learn that too. And they said, well, you're hired. And that's how I got into cybersecurity. I was blessed and fortunate and still thank those guys every single day for giving me a chance. And I've never left the business and will probably never, probably never will. Yeah. And I think cyber has done better than long distance phone lines over the years, right? Much better. Much better.

[00:08:33] I worked for WorldCom, if that tells you anything. And, you know, I don't think they're even around these days. For good reason, apparently. For a good reason. Yeah. For a good reason. Well, actually, it's interesting. You mentioned Network Associates days. We're going to go back to those days. You know, for those that are listening who their career doesn't go back 25 years like Robinized does. There was a company called Network Associates. It was different business lines in there.

[00:09:02] There was an AV1 called McAfee. There was a security business line called PGP. And we had a bunch of things in there. And then there was a network management called Sniffer and a help desk called Magic. And you and I were both in the PGP security business unit literally 25 years ago this month. But something interesting happened. We had a bunch of products in our division, one of which was something called PGP command line, which is basically a command line encryption tool. And it was exactly what it says in the tin, right?

[00:09:32] You'd go to a command line. You'd type some commands. You'd encrypt things and decrypt them and things like that, all from a command line. You know, the least user-friendly thing you could imagine. And we used to sell it for, I think, like $100 or $200 a license. And if you're lucky, you sold two or three licenses, right? This was not a high-ticket item. However, despite all that, Rob, I think you were the one that kind of figured out, actually, we might be able to sell this for a little bit more because you could have understood how people were using it.

[00:09:59] And so began a journey that lasted a few years about selling the PGP command line for more. Take us back to that moment. What was the realization you realized there was some value here beyond just something called an encryption command line tool? Yeah. No, man, those are good days. And by the way, kudos to you for remembering all those different moving parts of what Network Associates was. And I mean, I don't know if you did some research before that or if you actually just remembered, but that's fantastic. That's fantastic.

[00:10:28] You know, there's two parts to that, really. And one part's quite funny because you never know as a sales leader how powerful, potentially demeaning, or in some cases, and in this case, motivating your words can be. You know, we had a sales leader at the time, I'll keep him nameless, who found out that I was selling this PGP command line, you know, sort of product. And, you know, came over to my desk one day and said, you know, hey, you know, you're the guy that sells this PGP command line or whatever. And I said, yes.

[00:10:58] And he said, man, you have got to have the most difficult and worst job in this company because, you know, PGP command line, you know, exactly like you just described. I mean, it's you're selling code, you know, you're selling like this one line of code. I mean, there is no UI. There's nothing sexy about it. You know, it's just basic line code for encryption, you know, which is like the least sexiest thing on the planet. And, you know, I could have taken that statement or that interaction with him one of two ways. You know, I took it as a motivator.

[00:11:28] And, you know, I was like, well, I'm going to show this guy that, you know, I may not have the worst job at this company, but I'm going to make the most of it. And you're right. You know, I then started to really kind of dig into, well, you know, what do people do with this? You know, and what is kind of the value behind this? And, you know, I started talking to my customers rather than just making it a transaction. You know, I made it an interaction, you know, with respect to, you know, can you help me understand what you guys do with this?

[00:11:56] And then I learned that, you know, a lot of the banking entities that we were selling this thing to were, you know, batching up these high value transactions. And they were, you know, running it on these big mainframes or these, you know, other middleware systems. And they were doing these big transfers every night.

[00:12:13] And then I started asking about the nature of the transfers and the value of the transfers and come to find out, you know, they're transferring, you know, millions of dollars worth of, you know, EDI transactions, commerce transactions back in the early days, you know, when everything was batch encrypted and all that good stuff. And, you know, I just started thinking about it. I'm like, golly, there's a lot more than a couple hundred bucks worth of value here, you know, based on what these guys are using this for and what's at stake.

[00:12:37] And, you know, then I just started, you know, this is back in the days when you could sell above list price, I guess, on the price list. I don't know how many organizations that probably allow that stuff anymore. But, you know, truth be told, I was doing that. And I just started trying some of those value points. You know, I was like, can I get can I get a thousand bucks for this thing? And people gladly paid. And could I get fifteen hundred bucks for it? And people gladly pay. And next thing you know is, can I get twenty four hundred bucks for this?

[00:13:01] And strangely, as you can imagine, I realized my quota actually went by way faster, you know, the higher the price point was. And these people were kind of lining up, you know, because they had to have this thing. They needed this thing. And there was a lot of value unlocked there. So and then, you know, to your point, I was thankful or I mean, I was gracious enough, I should say, to share that with my other peer sellers who also started doing the same. And next thing you know, it became a bigger business than I think anybody ever imagined. For sure.

[00:13:29] And in fact, I remember you ran that business. Yeah. Well, we both both kind of ran it for. You can thank me for that. Four or five years. Right. And we kind of built it up from two hundred bucks a license to a fifty million dollar business in just two or three years, which was a lot of fun. And remember this story, I think it was the RD up in the Northeast. And he was saying that one of his reps got a bluebird for this stuff. And I was thinking, you know, a bluebird for this, I don't know, maybe 10K, 15K, something like that.

[00:13:59] Right. No, her bluebird was like seven hundred and fifty thousand dollars or something like that. You know, someone, I think it was Verizon Business, called up and said, I've got this PO. Where do I, how do I post it with you guys? And she said, how much is it for? She said it was seven hundred and fifty thousand dollars. I was like, what? So it took something that, well, you took something that was, you know, just very, very low dollars into something that people would spend a lot of money on because of what it was used for. I remember going to a bank up in the North Central somewhere and the CIO showed up. I thought, well, that's weird. That's not normal. Right. In the meeting.

[00:14:29] And, you know, he said like 10 minutes in, he kind of started, you realize what we use this for. And I was like, what's that? He goes, well, we process about $40 million a day of transactions using your encryption tool. I was like, oh, wow. We should probably keep selling this stuff. Yeah. I remember it was crazy and, you know, it didn't require a ton of development. You know, I think we, you know, ported it to a couple of different platforms when we, you know, as the transaction and commerce landscape started to change.

[00:14:59] But tons of value in that. But just understanding and asking that question, I mean, how do we not ask those sorts of questions? First of all, it wouldn't have ever been a big business. You know, second of all, you know, no telling where the world would have been today. And, you know, quite frankly, you know, that value exchange, you know, was worth way more than we ever anticipated. It was just with a couple lines of code and a cardboard box. Yeah. I don't even know if there was anything in that box, but I remember I had one of the boxes on my desk, you know,

[00:15:27] just to display the fact that, you know, there was something of value there. And I don't know if I ever reminded that VP of sales that, you know, how much money I made on that business and all that good stuff. But those were good days. For sure. For sure. So let's talk about value, though, in cybersecurity. You know, I've kind of been working on this for a while. I know you have as well.

[00:15:50] Often the feeling is that, you know, if you look at direct value, it's much more about departmental or getting the team working better or, you know, shorter time to IOC to get better productivity. But how do you think about it, Rob, in terms of value, business value of what we sell and what it would mean for a company? Yeah. I mean, I think it's, well, I think it's a binary equation. You know, you either get it or you don't in a lot of cases.

[00:16:15] And I think, you know, look, just I think the best way to kind of expose, you know, and understand that is, you know, this is where the scoreboard matters. You know, I think if you're not producing a scoreboard with respect to, you know, where your customer is today, you know, the exchange of the transaction, you know, the promises, the expectations, you know, the outcomes that you're seeking, the use cases that you're driving and then tracking and measuring kind of, you know, what changes as a result.

[00:16:43] You know, that really is the value equation. And it should be demonstrable. You know, I think it certainly makes everybody's lives easier when it is. But really just trying to understand it. You know, I think I think we all get caught in this scenario where we think we know what the value is. But, you know, the world's a dynamic place. You know, environments are dynamic. Businesses are dynamic. Networks are dynamic. Infrastructure is dynamic.

[00:17:10] You know, so while we might see or know or understand a value equation in one place, you know, we might see it redefined readily in another. But if we're not open to that, if we're not, you know, looking at that, if we're not thinking about that, if we're not asking about it, then you might not know otherwise. And, you know, we might be selling ourselves a little bit short.

[00:17:30] So I think it's I think it's just part of the open conversation, the open dialogue and, you know, being willing to listen to how people actually derive value from your platform versus you wanting to to know how they derive from it. And what I've seen a lot, Rob, is is people who have the sellers have the desire to, you know, grow bigger deals and all the rest of it. But when they get in the heat of the moment on a on a sales call, they go back to talking about features and capabilities and letting the conversation just stay there.

[00:17:58] How do you think about what a rep should be doing to get out of that zone and thinking more about value? Well, I think it comes down to knowing how people buy. Right. Right. I think that's a big part of it. And, you know, oftentimes we get caught up, you know, feature benefits are for technicians. You know, the feature benefit statements are typically for, you know, the company. The feature benefits are typically for the competition. Right. In terms of how are you attempting to potentially differentiate yourself.

[00:18:25] But, you know, where people tend to see most value in a transaction or, you know, especially in the idea of a bigger deal, they want to know what they're getting for themselves, you know, in return. You know, are they taking a risk or is there a significant benefit statement in the risk that they're going to take? Is there some sort of benefit statement with respect to their career, their standing, their stature, you know, associated with you and the opportunity that you're providing them?

[00:18:51] And I think in a lot of cases comes down to the personal nature of it. Right. And not just the professional nature of it. I mean, think about that PGP command line conversation we were having. There was no feature or benefit in that conversation. Right. It was just about the business. And the enablement of that. And, you know, the guy that was on the hook, you know, to your point with the $40 million worth of transactions, that guy needed those things to go successfully. And he needed to make sure that there wasn't a hacker that was going to go out there and intercept those things. Right. That's all that guy cared about.

[00:19:20] And if he did that, you know, every single day and that 40 million grew to 80 million, grew to 120 million and 160 million and beyond, that guy was going to be made to look like a hero. Right. Because he was helping to enable the business to grow. So, you know, if you went to him and said, well, this deal, you know, is $10,000 a license or $100,000 a license, as long as he could connect the dots to that trajectory, you know, for him, there would be significant value in that. So, you know, I think it just got to broaden the scope a little bit, you know.

[00:19:50] Yeah. I think I talked to sellers about how, you know, with the power of all the gongs and the choruses and the co-pilots these days, you can listen to these call recordings. You can see the point in the conversation where you could take it down one path, which is what you talked about, or you take down another one, which is, well, tell me about your process and tell me which tools you're using and tell me how often you use them and what you're happy with and things like that. No, that's a bad conversation, but you're not having a value conversation at that point, right? You intentionally say, I want to take it over here.

[00:20:20] Otherwise, he might never get back to that spot. Yeah. And I think, you know, it's not always about, you know, what you do. It's about, you know, what happens if they don't, you know, have some of the things and the attributes and everything else. And, you know, that's where you get a chance to shift the conversation. You know, everybody always wants, I mean, look, people have this inherent nature. If I sense you've got a problem, I want to race to go solve it. But I may not fully understand your challenge, right?

[00:20:45] And your surface level problem might not be the same as your deep level problem. And, you know, the value unlock, you know, the people that do transaction versus do, you know, larger deals, you know, the people that do deals versus build long-term partnerships. It lies deeply than, you know, more deeply than the surface, right? So you got to really kind of dig down and cover that. Yeah, I remember back in those Network Associates days when we had all those products.

[00:21:12] I used to default, unfortunately, I think many did what I call buzzword selling. You'd ask a few questions, you'd be listening intently. And then suddenly they'd say something like, oh, I do that. Let me tell you all about it, right? Rather than hitting the brakes and going, let me just understand why you're bringing this up and what else it means and things like that. It's you got to slow down or speed up sometimes, I guess. Yeah. Well, you and I used to have these conversations, you know, back when we were talking about, you know, training and enablement and all this stuff. And I'm sure you probably still do have these conversations a lot.

[00:21:39] You know, the fine art of curiosity, right? Most people listen with the intent to respond, right? Amazing sellers listen with the intent to question, right? And, you know, that practice of curiosity that, you know, they make a statement leads you to your next question. You know, they give you an answer leads you to your next level of curiosity.

[00:22:05] And you just find that point, you know, now you do that insatiably, you know, it gets annoying. But, you know, you do that to a point where you really uncover kind of the root of it, where the real challenge lies, you know, where the real solve, where the real value unlock is. You just got to get a little deeper. And that practice of curiosity, you know, makes a big difference. Otherwise, you're just being that passive listener with the intent to just respond as quickly as you can. And like you said, that's where the buzzwords come in.

[00:22:35] You know, the moment they say this, I'm saying this, and I'm going into my whole pitch. But you might miss most of the message in the process of doing that. Yeah, for sure. Let's change gears here a little bit, Rob. We're going to talk about comp plans. We're going to get controversial now. All right, good. Last week, I guess the Catholic Church, the Vatican elected a pope. And I made the comment that why does it seem like it's easier and more transparent to elect a pope than it is to get the comp plan out to the sales team every year?

[00:23:05] What is it? You know, you're being in the guts of behind the scenes about creating, you know, refining, aligning comp plans. And, you know, you and I have been in situations where we've not got our comp plan until like April, May sometimes of the calendar sales year, which is nuts. So what goes on behind the scenes that we're sellers not aware of that means that, you know, it takes so long to get these things out? Oh, man, what goes on behind the scenes a lot?

[00:23:30] I can tell you that, you know, these conversations typically start in the planning process, which for most organizations is about October, November. And to your point, Andrew, some cases last all the way into April and May. But I'll say, you know, I'll give both sides of it. You know, I would say from a sales leadership perspective and everything else, what happens along this a lot behind the scenes is a whole lot of advocacy on the part of the sales organization. Right. You know, I mean, we as sales leaders hope everybody understands.

[00:24:00] And I know I speak for my fellow sales leader community. We want everybody to make money. Sometimes everybody always questions. Well, I don't know if your comp plan is a reflection of your desire to allow me to make money. Well, every sales leader out there, you know, certainly wants you to make money. So, you know, there's a lot of advocacy that goes on, you know, with respect to that. I think what often people lose sight of is that compensation is a budgeted expense. Right. You know, everybody thinks, well, compensation certainly it certainly is a part of the budget or whatever, but it is.

[00:24:30] And, you know, most organizations, you know, have this idea of what they're going to spend with respect to compensation. And you've got to go work a model that kind of benefits the company and benefits the sellers and fine tune that stuff in between. You know, I think what really bogs these conversations down is the organization not understanding its true north. Right. Because if you think about it, speaking of buzzwords, by the way, let's just play compensation buzzword bingo real fast.

[00:24:57] Like, in fact, why don't you actually play along here, Andrew? Why don't you throw out some buzzwords associated with the compensation plan that you often hear? All right. PCR is one. Accelerators, SPFs, attainment, quota credit. What you get paid on is different to quota credit sometimes. Yeah. Yeah. All these lots of different factors in there.

[00:25:21] Yeah. PCR, BCR, ACR, you know, all the CRs, right? You know, all the commissions. Net and gross. Yeah. Net, gross. You've got ACV, you've got TCV, you've got ARR, right? All the ways in which you can count dollars and everything else. And what you don't, what I think most people don't understand is that is the construct of the plan can't be built to contradict the company goals and vice versa.

[00:25:47] Right. So, you know, a seller might be sitting on a on an ACV, TCV sort of compensation plan. But if the goal of the company is to actually grow recurring revenue growth and the compensation plan of the seller is actually in contrast to the actual, you know, company goals. So got to make sure all those things align. So if the company doesn't have a true north with respect to how they want the revenue to fall, then then the sellers, you know, quite frankly, might be operating at a bit of a point of friction of the company goal.

[00:26:17] And I think so most of the stuff that happens behind the scenes with respect to how do you create one of those things and how do you get it approved and how does everybody get excited about it? It's just about alignment. Right. And, you know, got to got to pick what the true north is. If the true north is recurring revenue, then you go create a recurring revenue compensation plan, you know, and you just don't, you know, emphasize or pay the same on non-recurring items. If your compensation plan is around, you know, ACV or TCV, then you pay people for duration.

[00:26:46] You, you know, do other things, but you just got to make sure you know what you're playing for. Any favorite comp plan terms or compensation elements that you've seen over the years that you think are at least eyebrow raising? Well, I mean, I don't know terms, but concepts, you know, I mean, you know, you introduce the concept of caps. I can assure you you're going to raise some eyebrows. You know, you introduce the concept of no caps. You're going to raise some eyebrows.

[00:27:10] You know, so, you know, I think I think if you asked any seller out there or anybody that's ever made any money, at least significant money on a compensation plan, you know, it comes down to cap or no cap. I don't know how controversial that is, but I mean, that's that's really what it comes down to. And then, you know, those rate structures. But the other thing I think everybody needs to understand is that, you know, it's all math based, you know, right.

[00:27:35] It's those rate structures are all a function of your variable compensation, you know, in relation to your quota. And, you know, if you want to go out there and, you know, everybody always wants to negotiate a compensation plan. If you want to be in a position to negotiate your compensation plan, you better know what you're negotiating on because you don't negotiate on the rate. Right. What you do is you negotiate on the variable comp and or the quota. Like just don't go and negotiate the rate because everything is math based. Right.

[00:28:01] So there's a little bit of behind the scenes wisdom. And I don't want any of my organization to be listening to this and come back and negotiate all their quotas and compensation. Right. So. Well, however you roll out your comp plan, I remember, oh boy, 20 years ago we were at a company and a new sales leader came in. What you don't do is what this sales leader did. Right. Rehash the comp plan. And basically the big change was we were getting paid rather than grossing up on channel deals. It was all going to be net. Right.

[00:28:31] And rather than just come out and tell us what the differences were and all the rest of it, initially you can, you know, you can pay on net rather than gross. The headline that the sales leader did rolling out was I'm increasing your PCR. And, you know, everyone's like, oh, this is great. This is getting paid more on deals. This is all going to be awesome. Right. And I remember being in a room with a bunch of salespeople as we're kind of listening. And we're also looking at the comp plan. And the first person goes, you see the third paragraph down on the second page? And she's like, no, and everyone starts looking.

[00:29:00] And that's when we realized that actually we're going to get paid less because of what are we getting paid on net, not gross. Right. And rather than just coming out and being honest and saying what it was, he tried to kind of hide it behind some big, you know, headline saying, I'm paying you more in deals. And it was actually really embarrassing because there's people coming on the call going, oh, this is awesome. I'm so glad you're doing this. And, you know, what a great leader. He was like, you know, listening to, you know, North Korea, you know, this is just awesome. And everyone else is going, have you not read page three yet? Yeah. Yeah.

[00:29:30] One of those moments. Yeah. Were you one of the guys that was excited about it or were you one of the guys that read the fine print? I mean, which guy were you? I think I was probably like the third person in the room to get to the fine print and go, wait a minute here. But no one, no one went on off mute and said, excuse me, I have a question. No one had the guts to do that. I will tell you, you know, it's funny you say that because I do remember that moment. And I was never a read the fine print guy.

[00:29:55] You know, thankfully, I had guys like you that were read the fine print and, you know, would send a little email or group message or whatever and notify everybody of like paragraph three. But I will tell you, you know, there's a lot of people out there that do read the fine print. And in my experience, you know, it's always better to basically expose the fine print than it is to get somebody to read it. Because you're right. That that conversation went from good to bad hurry. It's trust, right? I mean, yeah, I think he sent himself back actually with the sales team for months and quarters on that. Yeah.

[00:30:24] It was like there's the guy to try to pull the wool over our eyes. Exactly. Yeah. And when once you lose the I mean, salespeople, you know, this as well as I do, you know, we're all skeptics to begin with. Right. You know, and but if you do anything to go feel that skepticism, then, boy, you really got your hands full at that point. Yeah, for sure. Let's move on to hiring. There was a post on LinkedIn from Jason Lemkin in the last week. Jason doesn't know he heads up Saster, founder of CEO of Saster.

[00:30:52] They've been actually going on this week, actually, in San Francisco. He's a prolific poster on LinkedIn, some of which is spot on, some of which maybe not so much, I think. But here's a post that he did. He says, judge me if you will. But I would never hire a sales exec that is slow to follow up during the interview process. And a whole bunch of people chimed in with, you know, comments on the rest of it, some of which were, you know, how you do the little things is how you do the big things. Right. Supporting his idea.

[00:31:20] Another one said, quick follow-ups show care and drive. Speed builds trust and closes deals. Another person said, this is a no-brainer disqualifier of that salesperson in the hiring process. And then someone, well-known person on LinkedIn said, it's the worst. So, Rob, is it really the worst if a salesperson is a little bit slow to respond and follow up in the hiring process? Which one of those comments was yours? None of them. You didn't comment on that? I mean, come on.

[00:31:49] I'll tell you my comment in a second. Everybody knows that you're like one of the best. And if everybody doesn't know this already, anybody that might be listening or see this later, I hope they start following your commentary because you're one of the greatest LinkedIn commenters. I know. Like, I love your comments. Is it the worst? You know, I try not to never say never. And, you know, I don't like this idea of the worst or the last or the whatever else. I mean, look, it's situational, maybe.

[00:32:17] You know, look, now you're talking to one of the guys who's probably the world's worst follow-uppers because, you know, it's just like you don't have a lot of time on your hands to be able to do all that. And the world comes at you fast, personally and professionally. I think situationally, you know, you got a guy that, you know, wants a job and you need a guy and everything else. You know, I would expect a fairly quick follow-up. But, you know, like I try and operate with a little forgiveness and grace. And, you know, there's probably a reason for just about everything. And, you know.

[00:32:46] What red flags do you look for in your hiring role? Well, when you got guys like us that have been in and around the business for a long time, red flag number one is if I don't know anybody that knows you. You know, we've been in this business way longer than we look, I would imagine. Right.

[00:33:04] So, you know, despite our youthful appearance, you know, we've been around this block a couple of times that we've been blessed to work with people throughout this industry that, you know, lead companies, lead the industry, you know, are involved in all aspects of it. And if I can't go draw, you know, an indirect line or a direct line to you, then something might be wrong, especially if you're looking to go lead something, you know, in and around here.

[00:33:28] But I look at the human, you know, I look at, you know, are people going to be motivated by you? Are people going to be inspired by you? Are people going to be, are you going to be able to attract? Are you going to be able to retain? Are you going to be able to grow our talent? You know, all the important things. You know, are you going to be a servant to our people? Because that's what we're here for as leaders.

[00:33:53] You know, are you into that cause, you know, or is there a selfishness about you, you know, with respect to your mode of operation? So I might be willing to forgive somebody not having an immediate follow-up, but I'm not going to forgive you for not being an amazing human. I actually remember this. You probably don't, but somewhere along the way, we were involved in a hiring process somewhere.

[00:34:16] And you were pretty adamant about not hiring someone because in your mind, you didn't think the candidate was being honest about why they wanted to join the company or why they wanted the job. They were giving you the standard, well, it's such an exciting role and can't wait to, you know, list their stuff. And you're, you kind of rubbed between the lines that there's something else going on. And if that person had just said, look, here's my deal, here's what I'm trying to achieve, you probably would have quite liked the person. Yeah, yeah. I actually experienced this quite a lot.

[00:34:43] I mean, I just experienced this not too long ago, actually. We had somebody in and, you know, team really liked them and everybody really liked them. And quite frankly, I wanted to like them badly, but, you know, I kind of felt like the conversation was a little bit practiced and way too rehearsed. And I was hearing what I wanted to hear, but instinctively not what I needed to hear.

[00:35:02] And, and yeah, you know, I think people just need to be people and, and, you know, for us that have been around people long enough and everything else, you know, you kind of, you see a little bit through that and you don't want your spider senses tingling in the wrong direction. All I want to know is that it's in your heart, it's in your head and, and every bit of your waking moments and the desire and the energy that you want to put forth is for the good of, you know, our business and our people and everything else.

[00:35:30] But I don't need the narrative or the rhetoric or all the stuff in between anymore. So back to your original question. What did, what was my response to Jason Lemkin's thing about slower rep response? Here's my answer. I said, it's funny. I had never worked for a company that was slow to follow up with me during the interview process or ghosted me or made promises about the process that weren't real or had people interview me who weren't prepared or asked me lame ass questions or gave me an offer lower than we talked about.

[00:35:57] And yet this is all far more common and worse than a sales rep being slow to follow up. See, there you go. And you wonder why we love your commentary. That's genius. And I just, I'll tell you what, I don't know why. It just pisses me off. It's kind of, you know, holier than now. You know, if this rep doesn't follow up in half an hour, what sort of rep are they? And yet the companies are the worst people at just terrible hiring processes.

[00:36:18] And the way that I actually put it more positively is, you know, if you want to attract A players, you have to have an A player mentality about how you attract them and not sit back there and somehow think that these guys are going to flood to you because they won't. Right. And kind of the wider question after you is thinking like, what does it take to attract A players? Like what, you know, when you're thinking about there's people that you want to go after at different companies you've heard about or things like that. What kicks in in the Amesquil world to say that's someone we need to figure out how we get?

[00:36:46] Yeah, I think, I think transparency means a lot. You know, I think to people, I mean, to your point, I mean, you know, you, you get on these platforms and you see what everybody wants you to see and you hear what everybody wants you to hear. And, you know, everything looks amazing and everything else. And look, at the end of the day, a lot of what we do every day is a grind. Right.

[00:37:11] You know, people want to be around other great people and doesn't matter who you or, you know, what you do and where you do it, you know, as long as you're doing. But what does matter is who you do it with and who you do it for, you know, whether it's at home or in the workplace. And, you know, we all know that greatness wants to be surrounded by other greatness and, you know, mediocrity drives everybody away. And so, you know, I think, I think operating with the mode of transparency, I don't try and talk anybody into being wherever I am.

[00:37:38] You know, what I do is just tell them how it is and tell them what we need and tell them that we're going to do everything that we can to love them and appreciate them and grow them and support them. And like we talked about earlier, pay them, you know, in ways that are commensurate with their effort. And what we tend to find is that, you know, the good people are attracted to that narrative like moths to a flame. Right. What the good people don't want to be is sold on something. Right.

[00:38:08] Just like your customers. You know, strangely, everybody wants to be led to buy and people that want to buy into your company and your vision and your narrative and your direction, you know, want to be led to go. They don't want to be a part of that. They don't want to be told what they need to be a part of. Right. So I like to handle it. And, you know, and I've been blessed every bit of my career to be surrounded by amazing people. No doubt. No doubt. Let's let's move on to slightly different tone here, Rob. It's time for a section that I call visionary or high.

[00:38:38] I'm going to throw out some bold predictions about the future of sales and cybersecurity sales. And you tell me, am I a deep thinking, insightful visionary or did I wake and bake with some fine Colorado glue this morning before I got to my desk? That was easy for me to say. And for those that don't know Colorado Gorilla Glue, look up in chat GPT. Apparently, it's one of the more popular strains in Colorado. So am I a visionary? Do not do that on your corporate device, though. Yeah.

[00:39:08] Do it only on your personal device. Any force cut people listening, do not do it on your corporate laptop. So am I a visionary or am I Colorado high? Are you ready to go, Rob? I'm ready to go. By 2030, so what's that, five years, 80% of cybersecurity purchases under 100K will happen without a human seller or a human buyer, just AI agents buying and selling. Visionary or very high?

[00:39:37] Very high. Tell me more. I hope you're very high. I hope you're very high. Yeah. You know, I'm old school, man. You know, I still believe that, you know, people and people is what the buying and selling process should look like. And boy, if it gets to bot selling, you know, a bot seller selling bot buyers for everything under 100K, then I hope you and I are just doing this every single day talking about what the good old days were like. That's for sure.

[00:40:08] You're teaching the bots. Yeah, teaching the bots. Would you put the 100K might not be where it is. Where would you put the bar? Like 20K? 50K? 2K? Can I put the bar at no K? You can. You can. Not okay. Do you want this? Do you want this for the industry? I don't want it, but at some level. It's like saying, for my line, it's like saying, you know, back in the day, people would never buy anything on the internet, right?

[00:40:34] Because there's all sorts of reasons why you wouldn't put your credit card into a website and things like this, right? It kind of happens. And people buy cars and houses on websites now, it seems. Yeah. Right? So people would never get in a car without a driver. How's that? Right? And yet, what did we see last week or week before? So I don't know. I feel like to say never is, I don't think it's real, right? Because people buy stuff online right now. But 100K is a lot. That's really high, right? So I don't know. You'd be lower end of that somewhere.

[00:41:03] Yeah, the lower end of that, for sure. I mean, you know, I'm not going to lie. Chat GPT is quite a good friend of mine, you know, with respect to personal things. And, you know, I don't use it a ton in the workplace. But, you know, I did just ask it to plan me a trip the other day. And if it could have sold me the trip in the same process, I might have bought it from it. All right. Next one. In five years' time, more CISOs will report to CFOs than to CIOs and CEOs. And sales will shift to being a finance-first discussion.

[00:41:33] Visionary or high? Somewhere in between? Like a hands-on? Yeah. You know, maybe. I don't know what's in between. But maybe it's the mushrooms or something. I don't know. But I think this is already happening to some degree. You know, I think I haven't seen a huge trend in terms of the reporting lines.

[00:41:55] But I think we are seeing some trends with the support of the decisioning, you know, where security is becoming a larger line item for spent, you know, is the reality. You know, it used to be, you know, all the buckets were very separate. You know, now security is no longer a vertical bucket. It's more of a horizontal line across all budgets. You think about just in the development process. You think about in the infrastructure. You think about the network, the connectivity, you know, the devices themselves, the endpoints.

[00:42:24] And, you know, it just kind of goes across every bit of the line. I think it's becoming a bigger part of the overall financial equation, you know. And I think you tend to see it become, you know, not just about need, not just about compliance, not just about regulatory, not just about best practice. But you see it becoming very financial. And so I think a little bit of a mix of both. But those reporting lines, not super sure. What do you think? It seems like it's more financial in the last three or four years for sure.

[00:42:54] Everyone's feeling that right now is, you know, pretty healthy questions such as why would we do this in six months? We've got something else that's 70% good enough. You know, these impassionate kind of questions are being asked. To say a report to the CFO I think is a bit of a stretch maybe. But some people might, depending on the culture in their organization, view that as a positive compared to what they're reporting right now. Right? They may be wishing that they reported to the CFO. But I think in general it's a stretch to say that.

[00:43:22] But I think the scrutiny is probably here to stay from now on. All right. Two more questions. Last two. In 10 years' time, both the RSA Conference and Black Hat will be dead. Completely gone. Is that visionary or am I high as a kite? I think you're high. I think those things have stood the test of time. You know, I mean, you were at RSA.

[00:43:48] I was at RSA, you know, I would say it's still a very vibrant security community. I think like just about anything else, I think they'll morph a little bit. I think they'll modernize. I think they'll find ways to be relevant. But again, like we talked about before, I mean, you know, people love being around other people. Like this industry, and one of the reasons why, you know, guys like you and I have stayed in this so long, I would imagine, is it feels like family. You know, like I go back to RSA and it kind of feels like I'm going to a family reunion.

[00:44:17] You know, you walk down the street, you see people you haven't seen, you see people that you interacted, you see people who you grew up with in this career. You know, you know their families, your friends. I don't think, you know, and I think that goes well beyond us. I think that goes for the practitioners too. You know, I think in a lot of ways they show up not for the show and the circus and the circumstance, but they show up to be with one another and to engage with one another.

[00:44:43] And I think that networking aspect of it, that, I don't want to say misery because, you know, I don't think our industry is filled with misery, but that challenge that we all have that we share, you know, loves company. And I think they're great. You know, I think I love going there and showing up and seeing all the friendly faces from the past. Yeah, I don't feel it's going to go away, but I think it's going to change a little bit because it's, as someone said to me at RSA, you know, I've been coming here for 20 years and it's pretty much the same Congress as it was 20 years ago.

[00:45:13] I'm sure there are differences, but it seemed like this person anyway, it was very much the same place. Yeah, I think what does need to change a little bit, this might be slightly controversial, is, you know, what it's got to change is on the vendor side of things, right? With respect to, I mean, it really is actually a cybersecurity circus now. I mean, you go on the floor and, you know, it's some guy's got snow in their booth and somebody's got a robot or somebody's got a space alien or somebody's got a whatever.

[00:45:41] Like, I mean, it's like sensory overload. And, you know, I think we got to dial it down a bit. You know, everybody's like, you know, we got to stop starving for attention and really get back to the value oriented nature where that conference really started. Because I think a lot of the value stuff occurs in small rooms and small constructs and off the show floor and things like that. And I think the cost equation of it for the vendor community actually is starting to get a little out of control, too.

[00:46:10] Like, it's a very expensive endeavor for all of us, right? Yeah, I'm telling you, add in the booth and the setup and the people and the travel and the dinners and the hotel rooms and whatever, it's a multiple $100,000 gig for most companies. Oh, yeah. But I bet it's quite a moneymaker for San Francisco. And for Crosspoint Ventures, right, Rob? So, last question for you. Recently, Google acquired or announced they're acquiring Wiz and some hacks in the industry called the Combo G Wiz.

[00:46:39] So, prediction for you. Within 12 months, and this is for Ash if he's still on the call as well. So, within 12 months, Island, the enterprise browser company, will acquire the cyber hard platform from Dow's Technologies and rename the company Love Island. Am I visionary or am I high as a kite? I hope you're a visionary because that's a hell of a marketing message. But, yeah, I don't know. That sounds like a trick question to me. Oh, you think so?

[00:47:08] No, I think it's meant to be. It's one of these, you know… It is meant to be, yeah. It's a perfect marriage. Talking about love, right? It is the perfect marriage. Love Island. There's a TV show in the UK called Love Island, which is popular. I don't know if it's over here or not, but… Yeah, I think it is. I don't… Let me go check my… Let me go ask my wife. She's probably watched it a couple times, yeah. You're telling me you don't watch Love Island, Rob? I don't believe you're home, man. No, I don't. Well, on that note, Rob Ameskowitz, thanks so much for joining us today. Any final thoughts or comments before we sign off? Man, I love being here with you.

[00:47:38] I really appreciate it. Thanks for all the challenging questions. Thanks for your insights. Keep your commentary rolling on LinkedIn because that's really one of my favorite parts of logging on every day is see what Andrew has commented on and what's going to come next. I think you could actually just make a content career out of your commentary, but keep up the good work. Well, thanks, man. I appreciate the comments. Look forward to bumping into you probably at Black Hat or somewhere else and maybe do this one more time somewhere. I'm sure we'll see you soon.

[00:48:08] Yeah, absolutely. We should get Ash and some others on here too. I like that. It would mean a lot to me and to the continued growth of the show if you'd help get the word at. So how do you do that easily? There are two ways.

[00:48:33] 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. That's ratethispodcast.com slash cyber and explains exactly how to do it.

[00:49:03] Either of these ways will take you less than 30 seconds to do and it will mean the world to me. So thank you.