Vendors need to reach out to CISOs, but what does a successful approach look like? Too often vendors spray and pray with outreach, rather than doing the bare minimum of research. What should vendors do to try to create meaningful outreach to CISOs?
Check out this post for the discussion that is the basis of our conversation on this week’s episode co-hosted by me, David Spark (@dspark), the producer of CISO Series, and Steve Zalewski. Joining us is our guest, Adam Glick, CISO, PSG.
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Full Transcript
[David Spark] Vendors need to reach out to CISOs. But what does a successful approach look like? Too often, vendors spray and pray with outreach rather than doing a bare minimum of research. So, what else can vendors do to try to create meaningful connections to CISOs?
[Voiceover] You’re listening to Defense in Depth.
[David Spark] Welcome to Defense in Depth. My name is David Spark. I am the producer of the CISO Series. And joining me for this very episode, you know him, you love him, he’s one of our most quotable hosts, it’s Steve Zalewski.
[Steve Zalewski] Hello, audience.
[David Spark] In fact, I would say all our hosts are pretty darn quotable. I believe so. Our sponsor for today’s episode is Praetorian. They are your offensive security partner. Yes, they are going to help you by building a security program with you by testing your defenses early on in the development of your security program.
Great philosophy. I think you’re going to like it. A little bit more later in the show. But first, Steve, let’s get to our topic at hand. It seems like doing your homework on a CISO you want to sell to is the last thing most vendors want to do. This was essentially the complaint by Ira Winkler, who is the field CISO at CYE.
Now, he recently noted that out of over 300 vendor messages he received only 2 did the research to even mention books he published. Ira has published many books. Now, this extends to salespeople not being active in the overall cyber security community and only interacting for a sale.
So, Steve, overall, how do you like security sales professionals to build a relationship with you?
[Steve Zalewski] What I would say is to appreciate that you’re not selling speakers. That what you’re selling is a trust relationship, because we’re in essence working together to stop a common enemy that’s attacking all of our businesses. So, that mindset shift from one of consumer grade selling to enterprise and then enterprise security, I think, is part of the transition that we’re in.
[David Spark] That’s a very, very good setup for today’s discussion. I do also want to mention that I’m… This was an interesting discussion that Ira started. Most of the comments were extraordinarily negative against vendors. We are going to, along with our guest who I’m going to introduce in a second…we’re going to try to keep this as positive as possible.
But keep in mind, I’m going to be reading some very negative comments about vendors. Please don’t take this as personal attacks from me to you. The people I’m quoting, feel free to send them the hate mail if you would like to. I’m not actually inviting that.
[Steve Zalewski] I was going to say.
[Laughter]
[David Spark] But I will just say that I am quoting people. Don’t shoot the messenger is what I’m saying. Really is what I’m getting down to. But we’re going to try to keep this positive, to look for positive angles on this. And the person that’s going to help me with this, and help you with it, and help all of us with this is somebody who’s very tuned into the vendor community.
In fact, we had discussions about this at RSA. He’s been on our show before, and we asked him to come back again. He is the CISO over at PSG Equity, Adam Glick. Adam, thank you so much for joining us.
[Adam Glick] David, Steve, thanks for having me. Looking forward to this discussion.
What are the complaints?
3:22.779
[David Spark] Joseph Samson over at Cross River said, “Part of me thinks that they,” being the vendors, “might not actually care if one person buys or not. They just spam these out, hoping enough people do bite so they can get their quota.” Now, this comes to another issue that I have about the whole quota thing, and we can get into that.
Alan Porten of DXC Technology said, “I’ve seen a recent proliferation of multimedia lead generation companies that send LinkedIn requests. And if you fall prey, they instantly are spamming you. These companies are the problem. They need to be eliminated.
I must swat five to six of these a day.” So, there is definitely a high complaint on spamming, Steve, here. People don’t like it. It’s the spray and pray, which a lot do.
[Steve Zalewski] And to your point earlier, which is… But this is part of more of a systemic maturation problem. Here’s the challenge. We were just talking about this. There are about 4,000 security companies out there trying to sell product, which means they need 4,000 sales teams, and in-house, and channels.
That’s a lot of people. And so what they’re doing is they’re reaching across to sales folks in other industries and bringing them across. And so therefore they’re applying sales techniques that may work, like I said, for selling speakers but will not work for what we’re doing, which results in what we’re seeing – a lot of spam.
It creates a very negative feedback loop.
[David Spark] Adam, I think a lot of this problem has to do with essentially the pressures that are being put on salespeople. I bubble this up to the top of if you are measuring people by certain quotas… And the quotas are often the number of meetings you get, the number of messages you send out, the number of responses, not necessarily sales.
And if they’re being measured by this, spray and pray is the way to go, don’t you think?
[Adam Glick] Yeah. Guys, I’m torn, because if this didn’t work they wouldn’t be doing it. If spam messages didn’t work, there wouldn’t be spam messages. Someone out there is clicking. Someone out there is engaging. They are developing tangible leads that they can pass on to their sales team.
I don’t think that this is a thing where they’re doing something out of futility. There has to be some end that they’re getting a fruitful product from that the spamming is…they’re finding a return on it. So, when we think about it, it’s there. It’s prevalent.
They wouldn’t be doing it if it wasn’t useful.
[David Spark] But then there becomes the issue of, “Okay, I get 1 in 1,000 respond, and that could actually turn into a sale, and that’s totally worth it. If I send out 10,000 messages, and 10 responses…” I mean, of course I would keep doing that all day.
[Adam Glick] It costs you nothing. If I want to send 200 emails, I can make an Excel mail merge, and I can blast them out there, and it takes me 30 seconds. The downside or where there are the ramifications, I think, is the impact from your value or your perception as a vendor.
Is that you can start getting a bad name. There are companies out there that have the bad name, and we talk about them, and we make jokes about them because they’re notorious for these type of techniques.
[David Spark] Okay, so, Steve, I want to cut to you. How damaging can that be, or is there a balance?
[Steve Zalewski] You get to the so what, now what. Which is, yes, you can fill the top of the funnel with a whole lot of leads, but they truly are not qualified leads. They’re warm bodies. So, we’re getting into the used car salesman mentality of we’re then going to find you, and we’re going to hammer you try to put you under pressure to buy something and make it important.
That fails. That’s where we’re seeing now the damage being done to the ecosystem, which is it happened. Top of funnel is happening. Everybody feels good, but nothing is coming out the bottom of the funnel. It’s not 1 in 100. It’s 1 in 1,000. And so now everybody is being frustrated because it’s not working, but it’s the only way they know how to do business.
[Adam Glick] And to be clear, we’re just talking right now, Steve, about the generic nonsense spam. We’re not talking about the tailored things and other aspects about we’ll get to. We’re just talking about the noxious, annoying nonsense that comes through in our LinkedIn inboxes.
I can’t check my LinkedIn inbox. I’ve given up on it.
[Steve Zalewski] Right. It’s what we call inside sales. Cold sales, inside sales. What you’re basically doing is you’re dialing for dollars so to speak. That’s just it, which was for this industry, we have very little tolerance for that now because of what we’re trying to do, from a security perspective of managing attacks.
It’s rebounding on itself, and so it’s becoming ten times worse twice as fast.
What are they doing wrong?
8:37.068
[David Spark] Larry Whiteside Jr., CISO over at RegScale, said, “It’s gotten so much worse. I get people reaching out for my nonprofit. I ask them if they even know what my organization does. It’s a volume game at this point for them. But I will not respond.
I’ve tried to educate people, and some had the nerve to get offended, so I stopped. Not worth my energy anymore.” I’ve had that happen before. David Moore of Internet Safety Group said, “I’ve tested other sites like Facebook, social media, dating, etc., and I’m convinced that they are crawling with spam bots.
They never even look at your profile to see what you’re all about before they send out their pitch.” So, we’re going to spin this a little bit positive. We agree that this is happening. I think what happens is it gives a bad rap to those who are trying to perform well.
I always say it’s hard to be an injury attorney or an ethical used car salesman. They are given such bad raps generally. So, how do you sort of elevate yourself above a crowd that’s behaving poorly, Adam?
[Adam Glick] Yeah. And I think quick point on Larry’s comment there – it’s gotten so much worse? I don’t think it has. I’ve been doing this for 15, some odd years at this point. It has been a pretty steady baseline for a level. I don’t think it’s gotten worse in the relative years.
I don’t think it was better a long time ago. I think it’s been at this level for a long time. And, David, to your question there, Steve had hit the nail on the head right off the bat. This is a relationship game. Everything we do is based on the relationships of who you know, how well you know them, and how you can accomplish business together.
For me, that’s the key to success. It’s establishing these meaningful business relationships. You’re probably not going to be at that vendor forever. You’re probably going to be at that technology forever. I’m probably not going to be at my company forever.
Having these relationships we can lean on throughout a long career is where you’re going to find the success. So, establishing that relationship, building that rapport, and just driving to mutual benefit at that point.
[David Spark] That’s a very good point. And let me just ask you a quick follow up on that – do you have salespeople you’ve worked with at multiple companies?
[Adam Glick] Oh, yeah. Numerous of them. They might be at different companies, but I’m bringing them along. I want to see their tech. They have a respect for me. I have a respect for them. We’re mutually in this together. They can’t succeed without me, and I can’t succeed without them.
So, when we see these annoying span messages, when we see CISOs complaining, you’re just hurting the ecosystem.
[David Spark] Good point. Steve.
[Steve Zalewski] I’m going to go back to what we just said, too, which is… Adam said this hasn’t changed. It’s been like this for ten years. But what’s changed is ten years ago, we had 1,000 companies, many of which were practicing bad behavior for how they were doing sales leads.
But now we have 4,000. And so the volume of bad behavior has dramatically increased. I think that’s also added a lot to the challenge at this point is just the sheer number of people that are practicing bad behavior.
[David Spark] And they’re going after a very small audience, too.
[Steve Zalewski] They’re going after a small audience. This gets back to you hear us saying, “Well, then you’ve got to commit to the relationship.” Which is you have to do some homework. But many of these inside salespeople, they don’t understand security.
They don’t want to take the two or three months it takes to understand what it is that they’re actually trying to sale. Again, so the result is give me some talking points, let me dial for dollars. What we’re really doing is just creating more noise in the system, and we’re checking out more and more.
We’re doing less and less, and we do have trusted sales folks that we know. I would say sales folks that we know put the best interest of the company in myself first. They will never sell me something that’s in their best interest because they understand what we’re trying to do.
But that took years of times for them to invest in as well, and it’s very hard to expect these young kids or ones that are breaking or just being brought across to fill a seat to be able to have made that investment. And so another way to look at it is they’re basically being put through bootcamp and then being put on the frontlines.
We all know how well that works.
[Adam Glick] Yeah. Just to pile onto what Steve said, that happens. I’ll have a vendor who I’ve known for a long time. I’ll bring them in, and they’ll just say, “Hey, Adam, it’s not a good fit. It’s not going to work out.” And I respect them, and I appreciate that.
that is really, really powerful to me. When they say, “Hey, probably not going to be a good fit here. Probably not going to fit in the budget. We don’t work with that tech deck,” whatever it might be. I respect the hell out of them when they do that.
[David Spark] I hear that all the time, in fact, that the one biggest way to build trust, correct me if I’m wrong here, is tell me what you do and immediately tell me what you can’t do. Because the ones that say… You go, “Well, I need this, this, and this,” and he goes… The ones who keep saying, “Yes, yes, yes.
We can do it all,” thinking the way to close the deal is to say yes to everything and figure it out later actually has the reserve effect. Correct, Steve?
[Steve Zalewski] Yes. And what you find…and I agree…is people that have spent time in the industry, they know us. They see what it’s like through our eyes. And so to their point, they’ll go, “Look, let me just put it out there for you. I don’t think it’s a fit.
But let me just double check and give me some feedback.” Because it’s just a good opportunity to check in, spend 20 minutes together, give me some feedback, make sure you know what it is, and it builds the relationship. That works really, really well.
But there is just too little of that, and we understand why. We can’t expect the industry at this point, given the size and given the unreasonable demands many of them have based on VCs and having to generate an awful lot of revenue that they’re becoming desperate.
And in desperation, logic tends to go out the window.
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15:03.415
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What would a successful engagement look like?
16:29.157
[David Spark] Divya T. over at HackNotice said, “Sales teams often forget the importance of forming relationships. Meeting quotas shouldn’t be the defining trait of a good salesperson, especially in an industry where there are tons of vendors.” We reference this.
You guys gave perfect examples – same salesperson, many companies. Chris Zell over at Dell Technology said, “We keep getting the same question from salespeople over and over – how should we approach you. Why do I have to tell you how to do your job? You would think that part of their interview process might be something like, ‘So, tell how you would successfully pitch to a CISO,’ but evidently not.” By the way, that is a good question for a salesperson coming on.
Justin Perron over at 13 Layers said, “Blame middle sales management. They bring nothing to the table except telling people to smile and dial. They prevent a lot of quality connections between vendors and buyers.” Well, they do the smile and dial because, like you said, it works, and it’s cheap.
I mean, right, Adam? This is why these annoying things exist is because they work evidently. I don’t have the numbers, but they evidently do, right, Adam?
[Adam Glick] Yeah, they definitely do. And on your point there, I like that, how would you pitch to a CISO. The backdoor reference call, I have gotten that so many times where people have called me and said, “Hey, I saw you work with this technology or are looped into that person,” whatever it might be, “on LinkedIn.
How are they as a salesperson? What are they doing? What do they have?” That reference call is one of my favorite reference calls to take, just to be honest and truthful about my experience with a sales rep and how it’s been.
[David Spark] Steve, I want to get to Chris Zell’s comment of, “I think this a good question to ask a salesperson during an interview process – tell me how you would sale to a CISO.” I mean, that’s what they want to know, isn’t it? I mean, they’re hiring you to do that, isn’t it?
[Steve Zalewski] They’re hiring you to do that, but many of the people that are doing the hiring don’t understand what it’s like to be a CISO, and so therefore they don’t know what the right answer is either because they haven’t spent time in [Inaudible 00:18:43]
[David Spark] They’re looking for some creative brainstorming is what they’re looking for.
[Steve Zalewski] Right, exactly. So, they’re looking to hire somebody who has that answer because they’re technologists, and they’re proud of the technology. They don’t really understand how the technology has to be used and abused and validated for a CISO to be able to make the business case for it.
[Adam Glick] I think there’s a sales cycle, and how do you do that initial sales point. How do you break the ice? How do I get into that organization? That’s tough. I think the way to do it and where I’ve really appreciate it is the network. It’s not the first time I’ve done it where, “Hey, I saw a technology I really like.
Hey, let me introduce you to two or three CISOs that also have a similar problem. I’d love to connect you with them.” That’s the way to break it. It’s the, “Hey, Adam, I saw you’re connected with Steve. Could you connect me to Steve? I’d love to chat with him about what we’re doing and how we’re doing it.” That, to me, is the best way to sell the CISOs.
If you can get somebody to vouch for you, a fellow CISO in the industry, that’s worth its weight in gold as opposed to a cold call, a steak dinner, whatever we’ve got going on.
[David Spark] Agreed. And we hear that all the time as well.
[Steve Zalewski] I also will say I’m trying to be positive here, which is what we’re starting to tell everybody is you’ve got to invest time in the relationship. So, anticipate it’s going to take three to six months before you start to be affective, but that’s just way too long because nobody is willing to do that.
Because how often do you see the sales teams just churned through? “You guys were on. You didn’t do it. We’re bringing in somebody else.” Well, they’re not bringing in qualified candidates, they’re just bringing in different candidates. And so we’re starting to tell people, “Go work with local ISACA, or ISSA, or any of the local security get togethers.”
Where we’re simply saying educating yourself a little bit more, take the time. But if the company that’s hired you is not going to give you that time or give the investment in you to do that, that’s what we’re seeing. I can’t tell you the number of times that the security sales teams that I see or I talk to are folks that are being brought in from outside because it’s a churn and burn mentality, again, because people don’t understand what it’s really like to sell into this.
And so I hate to say it, but if you think about it, it’s like trying to sell into doctors. Okay? And so I’m a cardiologist…
[David Spark] Wouldn’t a field CISO who works for a vendor really have the insight? Because most field CISOs that I know were formerly a CISO somewhere else that was not a vendor. Adam, you’re shaking your head. What do you think?
[Adam Glick] Yeah, I think most of them have, and they have an understanding of that. The problem we’re facing here is this is… We’re talking about very [Inaudible 00:21:35] approaches. We’re talking about the best way, which is rapport, relationships, field CISO.
The solution to the spam, and outreach, and blasting, I don’t know. I don’t know how to do that. I don’t know how to resolve that issue. But to your point, David, yes, the field CISOs, they’ve been there. They’ve done that. They know what it’s like. Lean on them for it.
I worked for a sales organization. I can count on my hand the amount of times salespeople came to me as the CISO and said, “Hey, Adam, how do I sell to you?” That relationship doesn’t seem to be there as much as it should be.
[Steve Zalewski] And at the end of the day, you have to fill a pipeline because you’re obligated to follow the sales process that says fill a pipeline. And so you want to fill it with quality, but at the end of the day you opt for quantity because it’s the only process you know.
It’s kind of what we talked about. And so therefore you get to are you a strong enough CISO or a strong enough team that can push back to go, “You know something? I’m not going to accept pipeline for pipeline sake.”
But most people, most founders, can’t do that because they’re working with VCs. They have set expectations. And so the process just constantly then reinforces bad behavior, and we’ve got to break that cycle. And so I don’t have a good answer for that.
I understand what’s going on, which is why I don’t want to place blame anywhere. But as a security community, all of us, we kind of got to look at each other here and say look at what the consequence is. So, how do we hold each other accountable where we all want to buy product?
We want everybody to success, but we got to rationalize here somehow.
Who’s losing out there?
23:19.010
[David Spark] Bob G. over at Stargena said, “I aggressively block people on LinkedIn. I think it helps. But even as I do, I feel for the sales folks who have to do this.” Do the work of selling to CISOs. “They are hungry and seem to have no other way to try.” Karisse Hendrick of Chargelytics Consulting said, “Lazy sales reps create an opportunity for those that are different to stand out in unique ways when they listen to those of us who know this space.” All right, I want to lean on that last quote right there.
And one of the things we talked…
We did a whole episode about hiring not too long ago, and one quote that we read was, “Hack the process.” Not hack the individuals but look at the process, and how can I hack it to stand out. Now, I’ve seen “examples” of this of little tricks that salespeople have figured out like holding up a photo or a video of them with a sign that says, “Hi, Steve,” on it.
And then once one person does it then there’s a flood of them doing it. But that is one example of a way of hacking the process, but it’s just sort of like it’s a fly by night option. So, let me ask you, both of you, what are ways that you have seen salespeople “hack” the process that you have seen affective?
Maybe only affective once, not multiple times. Adam, I’ll start with you.
[Adam Glick] Yeah, it’s a fine line for me. Unfortunately I’ve seen the creepy ones. I’ve seen the, “Hey, Adam, I went through every detail of your LinkedIn profile, and I saw you went to this college. I saw you did this thing. I saw you’re part of that group.” And they throw the gamut at me.
To me, it’s a little off putting. It makes me feel a little creeped out, like an invasion of my privacy. So, I think there’s a fine line. I agree, David, you have to hack the process a little bit to get ahead. Customization, personalization, those are really nice touches to me, and they might get a read.
Unfortunately, the who’s losing out here is everyone. There is just such a sea of noise out there. How you separate yourself, to me, customization, personalization without going too far into the creepy land of, “I saw you went to this college. I bought you a sandwich from a deli around the corner from that college, and I mailed it to your personal house.”
[David Spark] [Laughs]
[Adam Glick] That’s the line for me. So, just be careful. Take a little bit, add some personalization. Just don’t go too far please.
[David Spark] That’s a good point to make, because one of the things I always say is your goal is a response. A positive response. And not of, “Hey, let’s bet on the Super Bowl,” kind of a thing, and, “I’ll send you a jersey of your favorite team.” But just what’s a way I can engage with you, Steve, that you would actually want to respond to me?
What do you think of that?
[Steve Zalewski] What I say is be respectful. The joking and, “Oh, this is my third time, so either the dog ate your computer…”
[David Spark] Yes, I know.
[Steve Zalewski] That’s when I get back to security is not a fun thing. It’s a rewarding thing, but it’s not funny.
[David Spark] But also if I don’t know you, it’s not… I shouldn’t be making jokes if I don’t know you.
[Steve Zalewski] And that kind of stuff, which is be respectful. Definitely show that you’ve at least tried to understand. You know what I mean? That there’s something there. That sets you up, and then you just got to hope this is your lucky day where I read that, and I either have five minutes and say, “All right, hearts and minds, one at time.
I kind of liked your approach. Let me at least give you a response because I’m trying to do the best I can. It’s only going to be one a day, and maybe it was your lucky day.” So, you have to set yourself up to be lucky, and that’s the best I can offer.
[Adam Glick] I would add, be a human. Don’t be the class clown. Don’t be this incessant nag. I’ve seen it before, “Oh, the third email, the fourth email, you must be on an island somewhere. Blink twice if…” I’ve seen it. Just be a human. Talk to me like a human.
If there’s something there, if there’s a relationship opportunity to build or to come in and check out the technology, I want to do it. But I’m not going to do it if you’re just not going to recognize me on the humanity level.
Closing
27:49.599
[David Spark] Essentially all relationships, they just begin without essentially jumping into bed. Sometimes people do want to jump quickly, but at least there’s something happening before that. Well, that brings us to the end of the show. I want to ask both of you your favorite quote and why.
I’m going to start with you, Adam. I know we tilted very negative with a lot of these quotes, so it’s okay if you pull a negative quote because that’s the lot in which you have to choose from. But tell me your favorite quote and why.
[Adam Glick] I think for me the favorite quote was, “The sales teams often forget the importance of forming relationships. Meeting quotas shouldn’t be the defining trait of a good salesperson, especially in an industry where there are tons of vendors.” I can’t stress that enough.
We are in a relationship business. How we operate is based on mutually beneficial business relationships. If you don’t have any sort of business relationship with me, I’m probably not buying your tech. There’s a bunch out there. There is probably someone I have a good relationship with.
I’m more likely to do business if I trust that person, if I know them, if I’ve seen them before, if I’ve talked to them. I can’t stress it enough – build that relationship. Work on strengthening that, and then everything else will just come.
[David Spark] That’s from Divya T. over at HackNotice. All right, Steve, your favorite quote and why.
[Steve Zalewski] Some good ones today. I going to go with Chris Zell at Dell Technologies, which is, “So, you would think that as part of the interview process you might be asked a question like, ‘So, tell me how you would successfully pitch to a CISO.’” Which I think gets back to doing your homework and looking at the industry, and somebody saying, “That should be a question.” If you don’t know how to sell a CISO, if you don’t know what a CISO is, it’s kind of probably a red flag that you’re not doing right by the industry and either find somebody else or don’t do it.
[David Spark] Very good point. Well, that brings us to the close of this show. I want to thank our guest, Adam Glick, who is the CISO over at PSJ Equity. Thank you very much, Adam, for joining us again. If you have any last comments on this, or you’re hiring, please let us know.
But first, I do want to also thank our sponsor, Praetorian. Remember, their web address is praetorian.com. That’s praetorian.com. Please go check out what they’re doing on their site because they can help you build a better security program with their offensive first security program to test your defenses at the beginning of your program, not an after the fact, not a compliance led, driven thing.
No. Build a better security program. Take a look at what they’re doing at Praetorian. Steve, thank you, as always. Adam, any last thoughts? Hiring, anything like that you want to tell us?
[Adam Glick] Yeah, careers.psgequity.com. We’ve got a ton of open spots. We’re looking for some security analysts. We’ve got a bunch of portfolio companies looking for talented security people. Please check us out.
[Steve Zalewski] That is awesome to hear. Thank you very much. Thank you, Steve. Thank you to our audience. We greatly appreciate your contributions and for listening to Defense in Depth.
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