Cybersecurity sales lives and dies on trust. So why do so many vendors burn bridges just to get a foot in the door?

Check out this post by Rinki Sethi, CISO, Upwind Security, 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 Geoff Belknap. Joining us is Octavia Howell, vp and CISO, Equifax Canada.

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Huge thanks to our sponsor, ThreatLocker

Full Transcript

Intro

0:00.000

[David Spark] Cybersecurity sales lives and dies on trust. So why do so many vendors burn bridges just to get a foot in the door?

[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 as my co-host for this very episode, one of your favorites, it’s Geoff Belknap. Geoff, say hello to the audience.

[Geoff Belknap] Hey everybody, it’s me, Geoff Belknap, and definitely not an AI replacement.

[David Spark] No, not an AI replacement, the real Geoff Belknap. I have seen him, he speaks to me, and he is not AI. I, on the other hand, may be AI. Our sponsor today is ThreatLocker. Allow what you need, block everything else by default, including ransomware and rogue code.

That would be ThreatLocker, our fantastic sponsor, and we’re going to be talking more about that a little bit later in the show. But first, let’s talk about the topic at hand, Geoff, and that is something that Rinki Sethi, who’s the CISO at Upwind Security, brought up.

And she echoes what we’ve heard from CISOs many times, and that is bluffing by a vendor is the fastest way to lose trust. Now, comments on her recent LinkedIn post about lying salespeople were replete with horror stories of vendors acting badly. Why do we keep seeing salespeople willing to damage their brand long term with this kind of false bravado?

And let me ask, have you seen this happen before?

[Geoff Belknap] Have I seen it in my entire career? Absolutely. Have I seen it recently? No.

[David Spark] So, that’s good. Something’s happening positively.

[Geoff Belknap] I don’t think this is commonplace. I do think, like, look, it’s sales. There are new people that come to sales, and there are people that are going to last a long time and build relationships, and there are people that are going to lie to close a deal.

Those people are not going to last, and that is a career-impacting choice that they are making.

[David Spark] Very, very good point. Well, there seems to be a lot of these issues still hanging on, and the “lying” has sort of, I will say, varying degrees, if we will, and we’re going to sort of unpack what that is. Joining us for this very discussion is the VP and CISO over at Equifax Canada, Octavia Howell.

Octavia, thank you so much for joining us.

[Octavia Howell] Oh, thank you so much for having me. I’m really looking forward to this discussion.

What would a successful engagement look like?

2:26.999

[David Spark] Michael Whiting of Hack the Box said, “Pushing a deal on a team which is not a good fit is something we’ve been told to never do in our team. It’s a practice which screws your long-term business goals, not just unethical, but damaging for your own reputation,” like what you said, “And for your entire organization’s.

Now, if a salesperson is telling you that their solution might not be the right fit or the right time for you and offers alternatives, even if they’re competitors, that’s the sign of a salesperson who is trying to help. Thankfully, the better sales teams these days are moving towards trying to consult rather than flog for their quota.” That’s impressive, and pretty much echoes what you just said at the opening in saying it’s not happening as much.

Mike Cushing of Patagonia said, “I don’t trust companies that reach out to me and say, ‘Our threat intel team found highly sensitive information about your company, and we want to share it with you,’ and then ask, ‘What’s your availability next week to meet with us?’ If it is so important, then provide me the information now.

It shouldn’t be held as ransom for a sales meeting.” Now, that example we have heard a lot of, so I’ll start with that one. Geoff, have you seen that, where they’re trying to say, “Hey, we’ll give you the information if you give us a meeting”?

[Geoff Belknap] Yeah, I have. That’s a really unfortunate one. My answer to that is usually the same thing. If you have something to report, here is my bug bounty and where you can report that, and I will absolutely action it. And if it turns out you were just being a nice guy when we get around to verifying it, I’m happy to have a conversation about it.

If you are one of the teams whose marketing or lead generation team has decided that dangling this scary email out is a good way to build revenue, I’ll tell you it’s a great way to destroy relationships before you ever have one.

[David Spark] Good point, all right. I’m going to throw this one to you, Octavia. Same thing. In both examples with Michael and Mike here, actually, one says some people tell you, “Hey, we’re not the right fit for you,” so they are really trying to help and be a consultant, and the second is the case of, “Hey, we found something, have a meeting, and we’ll tell you.” Have you had, let’s say, both of these experiences or one?

[Octavia Howell] I’ve had both, right, and so one of the things that I’ve always said is there’s a difference between a salesperson and a partner. In the first example, it’s really about partnership. It’s a long term, you actually are trying to make sure that you’re in it for us.

You’re trying to make sure that we have everything that we need, and you’re also partnering with other vendors that you know can actually help us. That’s really a partner, not a vendor.

The second one, I would not even consider that a vendor. In sales terms, they have this term called the rabbit, where that person is always kind of hopping around, trying to find a fit, trying to figure out where it can go. Those people to me seem like more rabbits.

Most of the time, whatever I’ve seen, when they say, “Hey, we found something we want to share with you,” it’s stuff that they haven’t even found. It’s stuff that it’s not a situation where, at least in my experience, we go validate, “Hey, let’s go check to see if they possibly did find this.

Let’s go see if we actually have an opening,” and most of the time, it’s not. It’s just a scare tactic, as Geoff said, to actually get a conversation. I’m not going to go for that. I don’t have time to deal with that. We have real work to do, and so if you have something that’s that important, please go to bug bounty, go report it.

Let’s fix it, but that doesn’t mean I’m going to have a conversation with you.

[David Spark] Back to you, Geoff, just very briefly. In the case of the second example, Mike Cushing said there with, “I want to share this information with you.” Have you had the more positive experience, like, “I want to share it, I have it, like where do I send that?” and that you’re just sort of guiding them down the path, and then that’s it?

[Geoff Belknap] Yeah, absolutely. I mean, look, if you are a real security company, forgive the connotation there, you would go that path first. If you’re really just trying to make sure I’m safe and protected, just report the information. We can talk later about, look, if that was super valuable, and I otherwise wouldn’t have had it, I will absolutely be interested in where you got that, and if there’s more of it, and how we can do business to connect that to what I’m doing.

But let’s be honest. The people that are using this tactic know that that information is not valuable. They know what they’re doing.

[David Spark] I think we all do.

What are the complaints?

8:04.660

[David Spark] Anatoly Chikanov of HealthEquity said, “One thing I would recommend to add is be up front of what you can’t do,” and I’m going to, by the way, echo this 12 times over. This we’ve heard a lot. Anatoly goes on to say, “I’ve seen far too many examples of where the product can’t really do something, yet it’s spun in such a fashion that isn’t really that big a deal, and we will address it some other way, which doesn’t end up working.

So, if you are honest about what you can and can’t do, that’s a solid foundation to build on.” I will just say I hear again and again, that is the biggest way to build trust. And Bradley Schagrin of ObserveID says, “Every CISO I’ve worked with would rather hear a hard truth than a polished bluff.

Vendors forget that when they spin, they don’t just lose a deal, they lose credibility. In this space, trust is currency, and once it’s gone, it doesn’t come back.” Bradley makes a very good point there. So, let’s just talk about the ugly truths that you have heard, Octavia, and has that turned into a solid relationship?

[Octavia Howell] I’ve had situations where we’ve looked for something, a vendor’s actually gone and found it for us because maybe they didn’t have the right fit. I also currently in dealing with salespeople where they’ve given me information or given me a product that does not fit my needs, even when I went and gave them my requirements.

So, as I said before, we kind of look for really true partnerships. So, I’ve seen both, and I really think that for me, my salespeople are partners with me, not just with the company, but also, they’ve developed friendships. And so, no matter where I am, no matter where I go, I may be able to recommend them to something else, another company that could actually be looking for something that they might have as well, but it’s really about those relationships.

[David Spark] Let me ask you a question. How can a vendor early on demonstrate that they will actually act like a partner and not just a transactional relationship?

[Octavia Howell] I would say they would take my requirements, they would try to figure out what we need. Anytime I get a 15-minute call, the first thing I tell them, “I do not care what other company is using you. I do not care what your market share is.

It’s just I don’t care about all of the first five slides in your deck. I want to know what your product does, and I want to know if it can help me.” The first thing, instead of showing me the product deck and who you already sell to, if a vendor comes to me and they said, “Hey, we just want to listen to what you need.

We just want to listen to what your environment is, what problems you have,” and then they don’t try to sell me anything on that first call. They say, “Let’s take it away, and we’ll come back.”

To me, that’s actually developing trust, and I’ve had a couple of vendors who do that. If I give them my requirements, and then they go in and they say, “Oh. Well, we can’t do this, but let me show you this, and maybe this can help.” That, to me, isn’t showing me that you were listening.

You weren’t listening to my needs. You weren’t listening to what I wanted. You were just trying to make a sale. That’s what I see, and that’s what actually builds trust with me early on.

[David Spark] All right, Geoff, I’m going to ask you the same question I asked Octavia, which is, what is the best way to demonstrate partnership, anything beyond what Octavia just said?

[Geoff Belknap] First of all, I’ll just say, Octavia hit the nail on the head. Like, look, if you’re sitting in the room with somebody like Octavia or I, you’ve already done the first step. Like, you’ve earned the trust. We don’t need to be proven that you’re worthwhile talking to.

Like, we’ve made that first step. Now what you have to do is show us that you meet our needs, right? And I think the first step of that is listening and hearing what our problems are and what we’re trying to do. And I think when we go through the meeting, it sort of starts that way.

I’m going to explain what my problem is because I want you to tailor the conversation to that. I’m going to listen to what you’re telling me about your product, and then I’m probably going to echo it back to you and go, “Oh, this is really interesting.

Do you do X? Do you do Y? Because I need to solve Z. And if you don’t, now is the time to tell me.” Or if, frankly, if you do it, but you’re like, “You know what? I do that, but I don’t know if it’s going to be perfect for your problem.” If you are just engaging with me even at that first step, I might be bouncing an idea off of versus somebody selling me a used car, that is a really good beginning to the relationship.

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11:11.295

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Why does it matter?

12:59.344

[David Spark] Tony Edwards of Silverfort said, “Saying we do all things for all people is setting everyone up for failure. Stop saying we cover all blind spots everywhere all the time. No, we don’t, guess what? Neither does the competition. What happened to under-promise and over-deliver?” Good point.

And Stanley Ogbu said, “In security, trust is the currency. Most CISOs would rather hear an honest ‘not yet’ than be sold a feature that doesn’t exist. Transparency not only builds credibility, it’s often the reason a vendor gets a second meeting or even a long-term partnership.”

And Aleksandr Kursov of Clarity said, “I see the fallout from competitors or other vendors over-promising and bluffing. By the time I show up, there’s already a layer of skepticism. People assume I might be the same. It makes me wonder how fair this is, but I also get it.

Once trust is broken, every new conversation carries the weight of someone else’s missteps.” And that’s a big one right there. I want to double down on that, Geoff. It’s kind of like the used car salesmen. There are completely ethical car salesmen, but we have this sort of vision in our mind of how that person should react.

It’s not right for us to prejudge, but I’m sure it happens. Yes, Geoff?

[Geoff Belknap] There are a lot of great salespeople out there, make no mistake, but I think everybody has run into one that wasn’t great or wasn’t their favorite. And I think it gives the whole profession a bad name, and I’m sure the great salespeople hate it because when you’re a great salesperson, you live and breathe and you know all of this intrinsically.

I think just going through a couple of these comments, if you are pitching a salesperson on a security product, they already know it will absolutely not work 100% of the time. That’s just part of the deal. They’re not expecting it to. If you tell them it does and you can prove it, like, absolutely.

You’ve got a customer for life, that sounds phenomenal. You don’t have to spread this sort of institutionalized trauma of trying to lie about your product and making me figure out where the lie is and where the actual truth is.

Let’s be honest about the fact that security is not a game where you can never be 100% sure. You know you’re always just making progress against the risk and the problem set. I know that, you know that. Let’s just be honest about it and figure out if your product helps me solve that problem versus trying to sell me on a fantasy.

Because when you do that, you’re really making the entire industry worse for everybody.

[David Spark] Yeah, Octavia, we have heard this before. Actually, the most popular article on our site is entitled Things That Salespeople Say That Set Off a CISO’s BS Detector. And one of them was claiming absolutes, claiming 100% of something, or “We catch all things.” And by the way, over the years, we’ve had various sponsors claim that on their site, and I send them a polite message and say, “You know what?

You’ve got this on your site. You may want to tone it down because it does not land well with us.” And I’m sure you’ve heard this too, Octavia. And I like the way you brought it up, Geoff, because don’t make me guess what’s the truth and what’s not the truth.

You don’t want to play that game, do you, Octavia?

[Octavia Howell] No, no, not at all. I actually think Geoff may be a little more gracious to salespeople than I am, possibly.

[David Spark] [Laughter] Well, you’re going back to my early comment. You’re prejudging that, yes?

[Octavia Howell] It’s not that I’m prejudging, no. I truly believe that salespeople have a job and they have a role to do. But I also know that there are sales engineers that actually may know a little bit more technical detail than the salesperson actually knows, and I feel like they need to come in a tandem.

When they come, at least when they come talk to me, I don’t want to only talk to the salesperson. I know that I have to build that relationship. They are the account exec. I understand that 100%. But when it comes to answering questions, I am not a policy/governance/business CISO.

Like, I do work with the business and I understand that. But my thing is I’m a little more technical. So, I need to really understand if it’s really going to work in our environment and if it’s going to solve my problems. I’m asking questions where it’s going to solve my problem.

And I feel like when I was promoted to CISO, I feel like I lost that when it came to talking to salespeople and sales engineers. Whereas I feel like when I was a engineer, I was able to get roadmap conversations. I was able to find out from the salespeople exactly what was going on.

[David Spark] So, you think they treat you differently with the CISO title?

[Octavia Howell] They do.

[David Spark] Really?

[Octavia Howell] 100%, 100%. And I’ve only been a CISO for four years. So, I remember [Laughter] what it used to be like.

[David Spark] Geoff, can you corroborate that? Do you think you were treated differently prior to being a CISO by salespeople?

[Geoff Belknap] Well, yeah, absolutely. I think at a bare minimum, salespeople and sales teams and regional vice presidents and CMOs or whoever get really excited when they’ve got the C-level executive engaged in the conversation. And frankly, that’s a mistake.

[Laughter] Especially if I’m engaged early, probably not a good sign. It means you’ve not properly vetted this conversation because if you’re starting with me, I don’t really know the problem that needs to be solved. Like I know it at a high-level altitude, but I’m not living it day to day.

I’m not going to be the best judge of what that is. And if you think meeting with me means the deal’s a lock just because I’m excited about the deck, you are misreading the conversation. I’m a nerd. I like talking about technology. I might get excited about it.

That has no bearing whatsoever on whether we’re actually going to do this deal.

[David Spark] Octavia, just echoing what he just said, were you living it more as an engineer than you are as a CISO?

[Octavia Howell] Oh, absolutely. Absolutely. As an engineer, I was given your roadmaps. They gave me roadmaps. So, the conversations were, “We don’t have this right now, but here’s what we’re building. Here’s our three- to five-year roadmap. Here’s what we’re going to have next year.” When now I have the conversations is, “We are absolute.

We solve all of your data problems.” Like, what does that even mean? Right?

[David Spark] [Laughter]

[Geoff Belknap] Yeah. I don’t even know what my data problems are.

[David Spark] But they’re going to solve them.

[Geoff Belknap] You tell me, that’d be great.

[Octavia Howell] They’re going to solve them. They’re like, “Oh, we’re a data security company.” I was like, “I don’t really understand what that means at all.” Like, yeah, we secure data. Sure. I don’t know what that means. Can you expound on that a little bit more?

Again, the conversations were completely different.

Who’s making money here?

19:38.272

[David Spark] Connor Anderson of Acuvity said, “I think vendors could sell significantly more if they went to each step in their sales process and asked themselves how they can be less risky for CISO/security teams. Limiting a POC to a tiny portion of the platform, risky.

Forcing every purchase to be bundled, risky. Vague answers when it comes [Laughter] to supporter implementation timelines, risky. It’s why the channel is so crucial to the security community. They help suss out the fluff. All right. So, I start with you.

I like this. They could do a better job addressing the risk at each step of the sales process. Have you had a vendor do that with you, Octavia?

[Octavia Howell] I don’t think I’ve had a vendor up front tell us what the risks were. We have had situations that we’ve had to reach out to the vendor and ask the questions.

[David Spark] But I think this is really forward thinking of what Connor is saying here.

[Octavia Howell] Yeah, I think so.

[David Spark] I mean, would you welcome this kind of conversation upfront?

[Octavia Howell] Oh, absolutely. We can actually put compensations in place if we knew well ahead of time, right? If we made a decision this is what we’re going to do, and we know what things we need to build out on our own or what integrations we need to do to cover us.

I would much rather that than to find out why we’re trying to implement.

[David Spark] All right, Geoff, I throw this to you. Connor puts forth a very interesting take on sales of identifying risk at each step. Have you had the conversation upfront, further down the line, at any time? What do you think?

[Geoff Belknap] To some extent, I have to say, this is the sign that whatever you’re trying to buy is maybe overcomplicated. It’s always really difficult. There are definitely some infrastructure things you need to do for security that are very difficult to just taste test and figure out if it’s going to work for you at scale.

But just naturally, that’s going to take longer anyway. Like if I run a massive telecom infrastructure or a cloud infrastructure provider or something like that, it is going to be very difficult to figure out how to get your solution in, exactly how we’re going to measure that it works.

But I think you have to, especially as the vendor, have to accept that look, it’s going to take a long time to even get to the point where we might be discussing buying this. This is just going to be a long sale.

And I think in this case, what Connor’s saying is brilliant, but it’s also the only way that it’s going to work. You’re not going to do a pilot and then immediately go, “Yes, I would like a million licenses or whatever for this.” Look, if you’re selling a security product, you really have to be honest about is this something that’s going to be simple to try?

Or is this something where, you know, my customers have very complicated environments and very complicated, differentiated needs. And if that’s the case, you have to approach this as a long-term relationship because it’s just not going to work any other way.

[Octavia Howell] I would also say that it’s up to us to be honest as well with our environment. Sometimes it is the salespeople that’s selling a bill of goods, but at the same time, a lot of times it’s us not being upfront with our environment and our infrastructure and wanting things to actually work.

Like we can’t put a square peg in a round hole. In some cases, I’ve had vendors come and they’ve had brilliant products and it just won’t work for us. And so, we just have to be honest.

[Geoff Belknap] I think it’s a great point. You have to be realistic, especially if you’re chasing a new vendor in the space. Their product might be phenomenal, but it might only be for somebody who’s a cloud-native SaaS platform. And if that’s just not you, if you’ve got any kind of technical debt or legacy in your environment, it might not work the same way it works for everybody else.

[David Spark] I want to stress, and I would love to close on this and just get confirmation, that is still a valuable meeting for a vendor because as we’ve heard again and again and again, CISOs talk to other CISOs about who you’ve spoken to that can solve problem X.

So, even if you don’t sell, that you’ve convinced another CISO that you’re valuable for someone is a value to the community. Yes, Octavia?

[Octavia Howell] 100%, and I said it earlier, right? Get on a call, you have a great product. If you’re actually upfront with us and you’re honest about, hey, this won’t work for you, but we’re love to stay in contact, that means that I may be able to actually, one of my friends may have the same problem or may have a problem and they have a different environment.

I’m going to recommend, “Hey, I’d talk to this person. I’d talk to this company. They may be able to help you.” And I’ve done that several times.

[David Spark] Geoff?

[Geoff Belknap] Yeah, 100%, myself as well. If it’s a great relationship, even if I’m not buying, I will go sing your praises to my friends.

[David Spark] Good point.

Closing

24:17.072

[David Spark] All right, now we are at the point of the conversation where I’m going to ask you, Octavia, which quote was your favorite and why?

[Octavia Howell] I think the quote by Anatoly was my favorite when he actually said he recommended to be upfront with what you can and cannot do. I think that was the one that resonated with me most because it is very much true. As I said before, we can actually have the relationships, we can actually work with each other or not, but if you’re upfront, that can set us up for a long-term relationship.

[Geoff Belknap] All right. Geoff, same question to you. Which quote was your favorite?

[Geoff Belknap] I really like Anatoly’s and I just have to share a personal anecdote here because I learned this the hard way, or at least a way that has stuck with me for decades now, or I just mean a couple years. Let’s pretend I’m not that old. I was working for a telecom provider, and we had one of everything, and I remember telling the CIO of the healthcare company, “Look, we can do anything for you.” He’s like, “Geoff, I know you can do anything.

You can sell me one of anything, but you cannot be good at all of it.” And that’s always stuck with me. It’s like, yeah, even if I’ve got one product that does everything, there’s only some of those that are any good for me. And I think that is really important for vendors to remember, and I think it’s even important for you buying stuff to remember.

But I think the other really important thing here is what Mike Cushing from Patagonia said, “I don’t trust companies that reach out to me and say, ‘Our threat intel team found…'” blah, blah, blah, blah, blah. Look, if the threat intel team found something, let me show you where to share that, or you can just email it to me directly.

And if it’s great, I will reach out to you and have a conversation but don’t use this as a way to scare people into conversations.

[David Spark] Very, very good point. Were you about to say something, Octavia?

[Octavia Howell] There is one more, we didn’t talk about it, but I actually have had where salespeople would actually reach out and they will say something that they know that you’re actually tied to. So, for me as a Black woman in security and a CISO, they will say, “Supporting Black women security,” and I’m like, “Mmm, that sounds very cringe.” So, I think one of the things that we kind of need to look at is kind of along the same lines of the, “Hey, we found something we want to share,” is really try to get to know what the needs are.

Don’t try to connect on something that you think is important or some type of label.

[Geoff Belknap] You can connect with somebody on a personal level after you built the relationship.

[Octavia Howell] 100%.

[Geoff Belknap] Don’t try to do it upfront.

[David Spark] This, by the way, takes many different forms. It also takes the, “Hey, why don’t we bet on the Super Bowl?” type version of that.

[Octavia Howell] Yeah.

[David Spark] We’ve gotten that version many times.

[Geoff Belknap] Hey, why don’t we violate company policy together?

[Laughter]

[Geoff Belknap] Would you like me to help you get fired? That would be great. Thank you. Perhaps I can help you take a kickback. Would that be great?

[David Spark] These are great, awesome ideas.

[Geoff Belknap] Thank you.

[Octavia Howell] Absolutely.

[David Spark] Bad advice from Octavia and [Laughter] Geoff.

[Geoff Belknap] From Octavia and Geoff. Tune in next time.

[David Spark] There you go. But no, I’m sorry. This whole show is filled with great advice. Thank you both so much. And I also want to thank our sponsor and that’d be ThreatLocker. Allow what you need. Block everything else by default, including ransomware and rogue code.

Remember, go to their website, threatlocker.com/CISO. Add that /CISO, easy way to let them know you heard about them from us at the CISO Series. Octavia, thank you so much. You were fantastic on the show. We loved having you on. Come back again! Geoff, you’re going to have to come back again whether you like it or not.

Hate to break it to you.

[Geoff Belknap] Oh.

[David Spark] And thank you to our audience. We really, really appreciate your contributions and for listening to Defense In Depth.

[Voiceover] We’ve reached the end of Defense in Depth. Make sure to subscribe so you don’t miss yet another hot topic in cybersecurity. This show thrives on your contributions. Please write a review, leave a comment on LinkedIn or on our site CISOseries.com where you’ll also see plenty of ways to participate, including recording a question or a comment for the show.

If you’re interested in sponsoring the podcast, contact David Spark directly at David@CISOseries.com. Thank you for listening to Defense in Depth.