The 3 AM Test: What CISOs Say About You When You're Not in the Room

Oct 30

Your demo went great. The CISO asked smart questions. They said they'd "review internally" and get back to you. Your AE marked it as a hot opportunity.

Then the CISO posted this in a private Signal group: "Anyone worked with [Your Company]? Thoughts?"

And got... nothing. Or worse: "Never heard of them."

That silence could just kill your deal.

The Channel That Actually Closes Deals

Most cybersecurity startups obsess over:

Website and search traffic
MQL conversion rates
Email engagement metrics
Demo-to-proposal ratios

Meanwhile, your actual win rate is being determined in channels you're unlikely to watch.

Private CISO Slack workspaces. Signal groups. Regional security meetups. Conference hallway conversations.

That's where CISOs validate vendors. That's where buying decisions actually happen.

And your AI-generated marketing content? It doesn't reach these channels. Ever. At least not in a good way.

What CISOs Are Really Buying

CISOs don't buy features. They don't even buy solutions.

They buy insurance against career-ending disasters.

After every demo, they're asking themselves:

When everything breaks at 2 AM, will this vendor actually pick up the phone?
Does this sales rep understand what I'm dealing with, or are they reciting a script?
If I bet my job on this purchase and it goes sideways, will they help me fix it—or escalate me to tier-3 support hell?

But more importantly, they're asking their peers:

"Anyone worked with these guys/gals? What's the real story behind the pitch?"

The Conversation(s) You're Not In

Here's what happens after your demo is complete:

Scenario 1: The Vendor With No Reputation

CISO posts in their peer channel: "Evaluating XYZ vendor for SIEM replacement. Anyone using them?"

Responses:

"Who?"
"Never heard of them"
crickets

Result: Your deal just moved to "Long-term evaluation" (which means no). The CISO isn't betting their career on an unknown vendor when there are safer alternatives.

Scenario 2: The Vendor With Weak Word-of-Mouth

Same question. Different responses:

"We evaluated them. Sales seemed good but their implementation team ghosted us after purchase … seems they are unfamiliar with some of the technical details in our stack"
"Product is okay. Support is impossible to reach"
"They over-promised in the demo. Reality was different"

Result: Dead deal. Even if you were the best technical fit, you just got disqualified by reputation.

Scenario 3: The Vendor With Strong Word-of-Mouth

Same question. Different responses:

"We've been using them for 8 months. Their team actually knows their stuff"
"They helped us through a messy migration. Support was solid"
"Straight shooters. They told us what they couldn't do and connected us with a close contact that could help us … which I appreciated"

Result: Your deal accelerates. Budget gets prioritized. Objections get dismissed. You're suddenly the safe choice.

Your Brand Is What CISOs Say When You're Not There

AI can write content about trust. It can generate the words "trusted partner" and "proven reliability" and “demonstrated resilience.”

But AI cannot create trust. And AI definitely cannot create word-of-mouth.

Trust and reputation come from:

Actually understanding the customer's specific situation
Being there when things go wrong
Speaking honestly about what you can and can't do
Having someone on your team who knows what a 3 AM ransomware incident actually feels like
Customers having something real to tell their peers about you

When your CISO customer tells their peer: "Their team was on a call with us within 20 minutes when our logs went sideways during implementation"—that's worth more than a hundred AI-generated case studies.

When they say: "Their sales engineer actually understood our SOC workflow without us having to explain it"—you just earned credibility you can't buy with ads.

What Your Competitors Are Doing Differently

While you're optimizing for MQLs and content velocity, your competitors with higher win rates are doing this:

They're building relationships in CISO communities - Not "selling," but actually participating. Answering questions. Sharing honest perspectives. Being useful without a sales agenda.

They're creating reference customers who actively advocate - Not because they got a discount for a testimonial, but because the vendor actually delivered what they promised and helped them succeed.

They're hiring people who CISOs already trust - Former practitioners. People from the community. Subject matter experts whose opinions already carry weight in peer channels.

They're documenting real situations, not sanitized case studies - Actual conversations about what went wrong, how they handled it, and what the customer would tell other CISOs.

They're treating brand and reputation as core GTM strategy - Not as a "nice to have" marketing initiative, but as the primary competitive advantage.

These are the stories you need to hear and be part of. These are the outcomes you need to share through marketing.

These scenarios build genuine one-to-one trust. Translating that authenticity into effective marketing allows the stories to reach and resonate with a much broader audience.

The 3 AM Test

Here's how to know if your brand strategy is working:

If a CISO had a ransomware incident at 3 AM and was scrambling to figure out what to do, would your name come up in the conversation?

Would someone in their network say: "Call [Your Company]. They know what they're doing"?

If the answer is no, you don't have a lead problem or a content problem.

You have a trust problem. And you're trying to solve it with tactics that will never build trust.

Sure, it could also be an awareness problem, which is another story. Stay tuned to this blog series for more on that topic.

The Hard Question

Look at your last five lost deals. Not the ones you lost out on because of price or timing. The ones where you were technically a good fit, but they went with someone else.

How many of those deals were lost because the prospect asked their peers about you and got nothing, or got something that made them hesitate?

You probably don't know. Because that conversation happened in a channel you're not in. And it happened after the demo, when you thought things were going well.

That's the channel that matters. And your marketing probably isn't reaching it.

What To Do About It

Stop optimizing for MQLs. Start building for word-of-mouth.

Start by creating brand awareness that genuinely connects with your target market and buyers. But awareness alone isn’t enough. You need to join and contribute to the conversations that matter most to them. When you say you care and will be there for them, it has to be visible and authentic.

This means:

Ensuring every customer interaction reflects deep understanding, not generic sales scripts
Creating content from people who actually know what they're talking about, not AI-generated “thought leadership”
Building relationships in CISO communities—not to sell, but to be genuinely useful
Documenting real customer stories, not sanitized case studies
Hiring advisors or team members who already have credibility in the community
Treating brand reputation as a measurable GTM strategy, not a marketing afterthought

If you can't point to what CISOs are saying about you in peer channels, you don't have a brand. You have a website.

Coming up: The five-minute audit to determine if your marketing is helping sales close deals or leaving them flat-footed in conversations that matter.

About Studio C60: We help cybersecurity and technology startups build trust-based marketing and go-to-market strategies grounded in deep product understanding and real buyer insights. With hundreds of products brought to market and deep and meaningful connections in the CISO and tech communities, we know what security leaders actually value in vendors.

Learn more at studioc60.com

About Sean Martin: Sean Martin is a technology and cybersecurity professional with over 30 years of experience in engineering, product development, marketing, journalism, and media. A seven-time CISSP-certified professional, he has led the engineering and delivery efforts for hundreds of cybersecurity products at some of the largest organizations and startups.

Learn more at seanmartin.com.

**Related Topics:** Word-of-Mouth Marketing, CISO Buying Behavior, Brand Strategy, Peer Recommendations, Cybersecurity Sales, Customer Advocacy, B2B Trust Building, Vendor Evaluation, Market Reputation, Win Rate