Everyone says they want the best security tools for their organizations. But sometimes the best tools are the ones a CISO can defend buying. The phrase “no one ever got fired for buying IBM” still rings true even if the vendors have changed. Why aren’t we more up front with this kind of motivation?

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, the producer of CISO Series, and Howard Holton, CEO, GigaOm. Joining is Tyler King, senior director – threat operations and response, Sinclair.

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Huge thanks to our sponsor, Material Security

Full Transcript

Intro 

0:00.000 

[David Spark] Vendors believe the features and value of their product is what’s going to make a sale, but a recent study of CISO buying patterns shows that’s not the reality. CISOs buy for reasons of risk to their company and, more importantly, for themselves.

[Voiceover] You’re listening to Defense in Depth. 

[David Spark] Welcome to Defense in Depth. My name is David Spark, I’m the producer of the CISO Series and joining me as a guest co-host and one of our absolute favorites, it’s Howard Holton, the CEO of GigaOm. Howard, thank you so much for joining us.

[Howard Holton] Thanks for having me, David. It’s always a great pleasure of mine to be here. 

[David Spark] We love having you on. Now, for those of you who don’t know Howard, he truly is one of our favorites. So you are in luck to be listening to this episode. By the way, if you have not checked out our other programming, go check it out over at CISOseries.com.

Our sponsor for today’s episode is Material Security. Detection and response for the cloud workspace is here. Specifically, I’m talking to those people who are working in Google Workspace and Microsoft 365. If you are in that space, you are definitely going to want to hear what we have to say about Material Security a little bit later in the show.

Howard, you shared a post on LinkedIn that most CISOs make vendor decisions based on their own personal risk mitigation rather than product features. The old “no one got fired for buying IBM” instincts, if you will. Now, you spoke of a company that lost out to another vendor, even though they had better tech and were 30% cheaper.

Why wouldn’t a company like that win out? What was the situation here? What’s motivating CISOs that many vendors don’t seem to get? 

[Howard Holton] So, the reality is every single product I put in place leans on the trust the company has in me. So in order for me to actually buy something, I have to trust that not only can they do what they say they’re going to do, but they make me look better, don’t make me look worse.

And that can just be they’re dead silent and never cause a problem. That’s fine, I don’t mind. Right? I’m not looking to wear a cape. I’m not looking for an S on my chest, but it absolutely makes a huge difference in whether I’m going to buy if I have confidence that you can actually carry the water that you said you can.

[David Spark] And that has a lot to do with whether you’re willing to make the purchase. All right. We’re going to talk about this in great detail because, by the way, your post blew up and lots and lots of great insight from the community. And somebody who’s going to join us in this very conversation, thrilled that he’s here.

I met him another conference call, and we’ve actually had his boss on the show before, too. It is the senior director of threat operations and response from Sinclair, none other than Tyler King. Tyler, thank you so much for joining us. 

[Tyler King] Thanks, David. So happy to be here. 

This is not just a security issue. 

2:57.249 

[David Spark] Kunel Patel said, “You’re not selling a product. You’re selling trust under pressure.” I love that line. “I’ve been on both sides, buying security products and watching vendors pitch them. We aren’t risk averse. We’re risk aware. We know who carries the blame, and it’s never the vendor.

Here’s what works. A, show me who’s used it successfully. Where’s the pain, adoption, and roadmap? B, give me customers who deployed without breaking anything. Let me speak to them. C, tell me the real timeline, lift, and people I’ll need. Keep it honest.

D, help me explain this to my CEO, board, and CFO in plain language. E, be honest about your roadmap and what you don’t do yet. F, prove your customer support. Be so good, it’s hard not to choose you. G, make demos relevant to my pain points. But here’s what kills deals – back channeling, going around me because I said no, or asked for more time.

That’s not sales. That’s undermining trust. Every CISO remembers which vendors did that, and that list gets shared. We’re buying career insurance. The vendors who win understand that.” Now, that was a long quote but wow, that was a good one. 

One more here from Ty Nelson of Google, “After years running security, I’ve learned every security purchase is a personal risk decision masquerading as a tech evaluation. The product is secondary to trust, proof, and survivability. I don’t buy tools.

I buy cover – cover for my team, my board conversation, my reputation, and my career. If a vendor can’t illustrate a clean track record, a speedy path to value, and a deployment story that won’t torch my ops, they might not make it to the first demo.

The ones who make my success defendable, not just measurable. The hard truth is features don’t close deals. Credibility does.” These two quotes kind of nail it. Yes, Howard? 

[Howard Holton] Yeah, I mean, again, the reality is I’m buying trust. So the more you do to remove that trust, the worse you are. And let’s be really clear. I don’t have to buy anything. I’m not going to get fired because I didn’t buy whatever the thing is, ever.

[David Spark] People don’t consider that. You have your direct competitors, and one competitor is do nothing. [Laughter] 

[Howard Holton] Correct. That is actually the competitor I pay the most amount of money to. The do-nothing competitor, right? The reality is until you get to the point where you give me a yes, I’m looking for the door, I’m looking for the exit. As the CISO, I’m triple-booked.

You get 15 minutes of every hour. So if I give you an hour meeting, if I can in the first 15 minutes, I just got 45 minutes back. That 45 minutes is glorious. I get to go to the bathroom and have a coffee, right? So really, I’m not looking for the opportunity to say yes.

I’m looking for the opportunity to say no. And the fastest way I say no is by you showing me that you can’t trust me, and my favorite way for you to do that because I will lifetime ban you, is when you attempt to go around me. 

[David Spark] Yeah. Nobody likes that. 

[Howard Holton] Well, not just doesn’t like it. Lifetime ban. There are vendors I will never buy from because their salespeople and their sales leadership went around a no, and in one case, reached out to my CEO through a board member to which I responded, “Not only will I not buy you, but I will never buy you as long as you work at this company.” 

[David Spark] All right. So Howard has put his foot down on this one. Tyler, you feel the same way. And also Kunel puts forth something we’ve heard a lot. If you want me to buy your product, you have to help me sell it internally. And a lot of vendors don’t understand the need to be able to sell internally, which I mean, I’m sure you’ve had this experience.

Yes? 

[Tyler King] Oh, for sure. I mean, we have so many vendors that we do so much work with, and I put them into two buckets for the ones that are here. We have vendors that they have their products. We use their product. It’s a great product. And as we said earlier, it just sits in the background.

It does its thing and it’s good. Right? Then I have my partners, right? Those are the vendors that I’m going to spend a lot of time with. They are part of my critical path forward on whatever that initiative is, and I’m putting a lot of my trust and credibility in the success of that tool or function or vendor, whatever they perform.

When we get to that level, right, I expect that credibility is table stakes, right? Part of that is not having salespeople reach out for additional licensing to my boss or his boss or going to the back channels of whomever. 

The other part of that as well is we just have so much that we have to focus on all the time, and when we have to then go evaluate for the 15th time that extra module because someone heard about the buzzword, right, that just is causing us to take away from the main mission, right?

And the credibility piece of that ties into that sales pitch piece so much. Kunel put it perfectly. We have so much that’s on the line when we look at different vendors, different companies, and we have so much criteria we have to look at because ultimately, it’s our name and our program that is on the line.

It’s not the vendor that will be reviewed at the board meeting, right? It’ll be us. It’ll be the specific program that that vendor sits in. So we have to be mindful of that and make decisions that take that risk and ensure we don’t have issues in the future because we didn’t look at something properly, they sold us something that didn’t work, you name it.

[Howard Holton] Yeah, I’ll also say looking at the response that you read, Kunel, was it? 

[David Spark] Yeah. 

[Howard Holton] One of the things I want, don’t set me up with one of your customers that’s going to tell me how everything was rosy. Set me up with someone that tells me how it failed and how you stood by them and fixed it. You want to knock it out of the park?

That’s how you knock it out of the park. It’s never perfect. I don’t expect it to be perfect. Show me someone that showed me how you were a partner and not just lucky. 

What’s the optimal approach? 

8:59.002 

[David Spark] Craig Garrod of ScienceLogic said, “The product/whatever has to work, but it’s the personal and professional risk in making the decision that makes the difference. My analogy is if the customer is in the trenches, will the vendor team be with you after you call them?” And Jason Little of ThoughtSpot said, and he’s quoting from a mentor, “People don’t buy the best software.

They buy software from people they trust. So many of the items you laid out are about trust. Trust in the software, trust in the viability in your industry, trust in ROI, trust in the implementation plan.” So Tyler, a lot of what both Craig and Jason are saying here echo what Howard just said at the closing of that last segment.

Yes?

[Tyler King] Yeah, I love, Howard, you put it perfectly. We have, again, we have partners that are vendors that are in the trenches with us. They understand what we’re going through. They’ve lived through the security issues that we’re facing in this day and age.

And they’re with us, right? They’re not sitting there in the background and hoping that we figure it out and then buy their additional module or license or what have you to get the job done. The second one from Jason, I think, is a big point that once you see them in the trenches, you can start to trust in what they’re doing, the ROI, the implementation, and I always feel like when they’re in the trenches, that’s the time to verify that they are someone that can be trusted to be there for the long run.

And again, that’s one of the designations, at least for me, that makes someone from a vendor to a partner, right? They’re there with us and they have a proven track record, not really on the tech side, right? Tech can be solved, but they’re there to help solve it with us and for us, right?

It’s not just about providing a software. It’s about all the things around that software that make it successful, that establishes and maintains that trust with that vendor. 

[Howard Holton] Well, a partner, by definition, must be as interested in my success as they are in their own. So if they’re just there to sell me and then parachute out, that’s a transaction. They’re not a partner in any way, shape, or form. And the number of vendors that do that…

I mean, my favorite LinkedIn outreach is, “I’m curious about how we can partner with GigaOm.” It’s like, “Cool, can you define partner for me?” “Well, we do this thing.” “So you mean just sell to me?” Because that’s not a partner. That’s not you caring about my success in any way.

[David Spark] I don’t ever like that as an opening line, and I’ve gotten that a lot. I mean, to me, it sounds like, “Hello, I’d like to sleep with you.”

[Laughter] 

[David Spark] It’s a little too much too soon. Yes, Tyler? 

[Tyler King] Yeah. I mean, again, I don’t know you, I’ve never heard of you. We haven’t spent any time on this together, right? Let’s see if it’s the right fit before we go into the next step of anything, POC, a demo. I don’t even want to spend time on those if I don’t even understand what you do or how you’re going to help me, right?

Have you done your research on your side? Have you figured out all the different pieces of that? If you’re not going to do the research on that side, before you talk, I’ve already lost faith we’re going to be in trust state in the long run. 

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12:14.631 0:00.000 

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What needs to be considered? 

13:35.748 

[David Spark] Dwayne Rendell of Rapid7 said, “When you say, ‘Ignore the CTO,’ maybe it’s local, but I find people are always trying to get to the highest person, ignoring the people at the coalface who were actually going to use the product. My theory would be reverse in many cases.

If you have a happy enabled team, they keep the place running, which equals happy CXOs.” I’ve heard this philosophy. I’m strong on that. And Ed Mohr of Seceon said, “When I hear that a product needs to be defensible, I think of companies that advertise on CNBC or the like, creating a perception that it’s carried onto the board.

I have spoken with CISOs about known gaps in these ‘defensible’ products, and they literally don’t care because the name is defensible. Yet many of these companies, if not all, have had substantial incidents, both self-inflicted and from bad actors, and they remain defensible.” Well, I can think CrowdStrike does mainstream advertising, but they had a horrible incident that brought down the airline [Laughter] industry, didn’t it?

So Howard, I’m sure the point of this sort of mainstream advertising is to get the name out as a brand name to “trust.” Yes? 

[Howard Holton] Yeah, without a doubt. The problem that I had with that entire response chain is, well, it’s fundamentally broken. The first part, work up through the organization, assumes that the vendor is arming a champion who’s never spoken with me and doesn’t understand what I care about to come sell the product to me, and then they wonder why it takes 18 months to get anything done.

It takes 18 months to get something done because an engineer has no clue what I care about, does not speak my language, and so they just lob crap to, “We need to buy this thing.” Okay, cool. Where does it fit in the budget? How does it work? What does it do?

What is the business value we’re going to get, and how does it enable the business to achieve its goals? Well, they don’t know because they’ve never thought about those things. Okay, cool. So did the sales team arm you to have a conversation with the CISO at all?

No? Okay, cool. So we’re starting from zero then. It’s not really going to help you to start from the bottom up. 

At the same time, if you come [Laughter] into my office, I’m not signing on it either. I’m going to ask you the questions I care about, decide whether the gate is open or closed, and then send you to work with my technical team so they can validate the technical bits.

On the second bit, which is the advertisement for someone like CrowdStrike and making them a household name, the fact that they advertise on CNBC doesn’t mean that they’re not good. Also, really easy to throw stones at the largest vendor in the space when you’re the smallest.

[David Spark] Oh, yeah, that’s punching up. Yes.

[Howard Holton] For sure. I hate punching up. At the same time, did CrowdStrike make a mistake? It was massive. It was huge. It was completely and totally preventable. It was a failure of process on their part after they argued with the entire industry to trust them.

We all should have considered that. Remember, they pushed auto updates because they convinced us at the board level that they were better at making that decision than we were. And then they pushed an update that destroyed everything. So it goes right back to trust and doesn’t go any further, but the fact that CrowdStrike did this, they’re the biggest player in that particular space, doesn’t negate the fact that the vendor that hasn’t yet just simply isn’t large enough to have had their turn at the wheel.

[David Spark] I want to throw this to you, Tyler. I want to go with the first thing that Howard was talking about is people from the bottom up, selling it internally. I totally hear your argument, Howard, but I think there’s an argument the other way.

Do you believe the argument the other way or are you on the same side as Howard here, Tyler? 

[Tyler King] I think that, again, every company and every vendor will at some point make a mistake, right? It’s going to happen. How big or small it is, hopefully it’s as small as it can be, but the answer is you’re going to have the CrowdStrikes, the SolarWinds 123 password for FTP that caused all the fun there.

Those companies in their response and reactions are what to watch. How did they come out of this incident? And how do I feel from a trust perspective? Did they tell me all the information? Did they realize what happened and made amends in that way, whether that be contractual and cost changes to how things work and the platform overall?

Those types of factors are the thing that make the defensible question, frankly, defensible. [Laughter] If you have a vendor that’s willing to show, “Hey, we messed up and here’s what happened and here’s what we’re going to do better,” you’re going to have a better time with that vendor.

The longer question that happens is after an incident such as the CrowdStrike one, again, that’s going to be the most stable EDR for one to two years after that incident happened, and we’re getting very close to that timeline I just said expiring. So where I’m at on that is how are they going to do now that they’re beyond the, “We have to be perfect on this for a little bit because we had such impact”?

That’s where you’re going to see the rubber hit the road for them and other companies that have had issues like that. And that’s where you can really get into the name brand and we’re going to stand by them, right? If they continue on that journey.

So that’s where I think it’s interesting on the CrowdStrike one as that kind of has unfurled is how are they going to be as the clock runs up on that timeline, and the investment that their board is giving for better technology, better program management, better development starts to be moved away or thought through as a cost center rather than we have to do this to remain in business.

I think it’ll be an interesting time to see that and that’s where I think this defensible piece will come into play is if they do move away from that, right, it’ll be a bad time for them, right? They only get one of these huge ones like they had. And after that, they’ve got to be as good as they can be forever.

It’s just a question of will they? [Laughter] 

Can anything be done? 

19:44.128 

[David Spark] Kraig Kraning of Flossy said, “We all do this naturally in our daily lives. Checking product reviews before a purchase online, sticking with brand loyalty even though the competitor is actually running promotions, or you’re avoiding a restaurant or brand because of ‘that bad experience we had at that one time,’ only taking risks when necessary and doing our best to not disrupt the apple cart of our lives.

But when a seller is up against quotas and deadlines, a lot of the common sense goes out the window. None of us would have friendships if we only ever talked about ourselves, never took an interest in anyone else, and simply pushed our agenda, and yet a lot of go-to-market motions feel exactly that way.

How different the buyer journey/experience would be if sellers showed up truly interested in the buyer instead of simply attempting to make their product sound interesting enough to buy.” So, Tyler, I’ll start with you. I’ve seen this. I’ve seen the dog-and-pony show, “Listen to our demo,” and I’ve seen the opposite where they just sit there and they talk to you about your business, which I think is smart because they’re gathering information about where your pain points are, which seems like a smart way to go about doing sales.

Yes? 

[Tyler King] For sure. I mean, I love the vendor that’s going to tell me out of the 10 problems that I have, they’re not going to solve all of them. No vendor will solve all of my problems, but a lot of the sales pitches that you go into, it’s the gold-plated key that will solve everything, right?

That’s definitely a go-to-market strategy that seems to be pretty prevalent out there, and it just immediately makes my eyes glaze over. I just don’t think that there’s any platform or vendor or solution or company that can solve every cybersecurity problem unless they have spent a lot of time building things specifically for that company.

And by the way, those problems are not going to translate to the next company. They’re going to have different issues. 

So, I think there’s a large requirement for vendors to come in with a bit more of an open mind and just talk through, “Hey, here’s some problems that we can solve. What are your problems? What do you got going on?” Right? And how do we take that and mold it together to maybe come up with a story that will then influence the rest of that interaction, right?

The demo should be tailored to the problems that we have. The licenses that you’re trying to pitch should be tailored to the problems I’m trying to solve. The end of quarter, “We want to get you more involved with this and we’ll give you this amount of discount” should be tailored to the fact that maybe the thing that they’re trying to get is not worth it for us to go buy.

It’s not a problem that we need to solve. So, I think that there’s definitely a better strategy there. 

And a lot of the vendors and partners I work with, I try to not get past their welcome slide on purpose. I don’t want to see the stories that you’ve talked through with 15 other customers today. I want to see the story that you’ve taken the time and built for us, and you understand our problems enough to be able to talk through it, and you’ve actually built the connective tissue inside of your environment to maybe bring an engineer or a pre-sales engineer, whatever you need to help get through any specific technical questions that come up.

But before I ask, right, you should know what the company is and what they’re looking for, right? And go from there. Not come in with your already prebuilt PowerPoint and presentation and, “How do we go forward?” And then back to the other point, obviously, “Oh, I didn’t get them.

I got to go get the CISO involved or his boss involved.” You name it. 

[David Spark] Howard, your take on this about the general approach? 

[Howard Holton] No more than five slides. First slide is who you are. Second slide is what you do. Third slide is who you’re right for. Fourth slide is who you’re wrong for. Fifth slide is just a big question mark. And period. End statement. If it takes you longer than five minutes to get through that, you’re burning time you don’t have.

The more I talk, the more you know about me. The more I talk, the more every human that talks about themselves feels, “Oh, my God, they really care. They’re really listening.” 

I’ve also just given away the keys to the kingdom in 30 minutes of talking. I’ve told you about me, what problems I have, what I’m paying attention to, what I’m not paying attention to, what I care about, what I don’t care about, all of it. All you have to do is ask questions and I’ll tell you everything.

The second you click Next on a slide, we’re done with that. Get through your slides really quick and let me talk. Use all of that to come back to the M2, to the second meeting, and go, “I heard everything that you said.” Cool. Now I’m listening to have you parrot back the things that I said, and you tell me how you can solve each one of them.

You said this was a problem, right? Okay, so when we look at customers that are in this space, really important thing, you tell me you have other customers that look like me, which means you have the ability to help me understand what I’m doing wrong, not just pandering to what I said I want to do.

Now you’re in something. Now I’ve got the sunk cost fallacy working. Now you’ve shown that you listen really well. You’re doing all of the things that make me want to continue this process. Far more likely to get a yes, far more likely to get a fast yes because now we’re getting into how do you matter for me?

What do you do for me? And what are the boundaries? What do you not do? It’s really important to understand that. And if you come in and go, “Oh, and we make coffee too,” I’m done. I have no space in my world for hyperbolic statements. Give it to me straight.

Talk just about what I care about. If at the end we can agree, you can solve the problem I care about. You can do it in the way that I need to. You can do it within today’s budget or tomorrow’s budget or make it worth it for me to go ask for more money.

Great. Then you can tell me all the other things that you do. But if I haven’t asked if you make coffee, don’t say you make coffee. 

[Tyler King] I’ll just add on to that, Howard. I mean, the biggest thing is we’re talking go to market. I see this all the time in QBRs, quarterly business reviews with vendors, where it’s one slide of what we’re doing with you today and 15 slides of, “Hey, this is the new licenses that we have, and this is what you could do if you pay us more and get these other features.” When some of those features, we will never, ever need, right?

We need that to be whittled down to the, hey, what are we doing today? What can we do today with you better? And what does the partnership and strategic value look like if we went into this other direction with other modules or whatever they’re trying to sell, right?

It expands beyond the go to market. It also expands into how they handle the continuation of the sales throughout that relationship. 

And back to my point, my partners, that QBR deck, 5 to 7 slides, my vendors, 30 slides with 2 of them being okay metrics and the rest being a sales pitch. The whole go-to-market strategy also flows into the rest of the relationship is what I found. So definitely something to be mindful of.

Go to market and QBRs, I feel like, are where I get those sales pitches and where we start to get eyes glazing over. And if you get the wrong people with their eyes glazing over at the wrong moment, right, because you brought someone in to look at the value.

That’s immediately back to the trust that we were talking about. You just lost a lot of trust as a vendor or partner because you didn’t cater that message better to what we need during those calls and meetings. 

[Howard Holton] It’s kind of fun. If you are showing a transaction and the CISO’s in the room, that’s what you are. You’re a transactional sale. Guess what? I’m not buying, I’m just not buying. Additionally, if someone who works for me brings me a transaction, they don’t bring me a strategic sale or a partner, that goes into a hat.

And then once in a while, I play revenue roulette and I stick my hand in the box of garbage that somebody would really like to have. And I pull out a name, and I go, “Well, it looks like this is what we’re buying now,” because you’ve showed me no differentiation on why you deserve more of my budget than anyone else.

You’ve shown you’re just a transaction. 

[David Spark] All right. 

Closing 

28:05.489 

[David Spark] This brings us to the portion of the show where I’m going to start with you, Tyler, and I’m going to ask which of these quotes – which there’s a lot of good ones here – which of these quotes was your favorite and why? 

[Tyler King] I’d have to go with Kunel’s. 

[David Spark] That’s the opening one. Yeah. 

[Tyler King] It’s a big one, and I think it hits on every single thing that we’ve seen to be reasons to either go with a vendor or reasons to move away from one, whether that be from a sales pitch or an incumbent that’s already there today. So I think, again, how does it work?

Be honest. Help me be able to explain it. What’s the real lift, the real timeline? Again, it might be a cheap product, but then if I need 15 people to sit there all day building it, right, that’s a whole different type of investment. So, I think that, again, there’s just so much there to unpack and they’re all great points and all the things there are questions to begin the pitch or the review with that vendor, not, “Here’s what we do,” right?

Show me why I should trust you with this thing. I don’t really care about the tech until you can show that you’re trustworthy and I can verify that with other customers, I can see the vision and the journey. You can show me how this is relevant to my pain points, you name it.

So that one really resonated with me for sure.

[David Spark] All right, Howard, your favorite quote and why? 

[Howard Holton] I’m going to go with the same one, but it’s only because it was a horrible cheat.

[Tyler King] [Laughter] 

[Howard Holton] His quote was really long, really detailed, and really nicely staged, so it kind of has to win. 

[David Spark] [Laughter] Well, that’s not always the reason we get winners just because they’re long and well-staged, but it was a great quote. I’ll agree with you. Well, huge thanks to our sponsor and that would be Material Security. Remember, detection and response for the cloud workspace is here.

If you’re in Google Workspace, if you’re in Microsoft 365, you need to check out what they’re doing over at Material Security. Simple to find, material.security. Go there and when you check them out, let them know that you heard about them from the CISO Series.

Huge thanks to you, Howard. Thank you so much for joining us. And also, thank you as well to Tyler for coming in and being on the microphone. We greatly appreciate it. And I want to say to our audience as well, we greatly appreciate your contributions, especially to Howard’s posts.

Do more of that. If you’re not following both Howard and Tyler, well, we’ll have links to both of their LinkedIn profiles on our show, and you can do just that. Please do that. Thank you for your contributions and listening to Defense in Depth.

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