Five Tests That Reveal Why Your Deals Aren't Closing

Nov 5

You're generating leads. Sales is having conversations. Demos are happening. But deals stall at the same stage, every single time.

Is it your product? Your pricing? Your competition? Or is it something else entirely?

The Pattern You're Not Seeing

Most cybersecurity startups blame deal stalls on:

"They don't have budget"
"The timing wasn't right"
"We lost to a competitor"
"They went with an incumbent"

But here's what's actually happening: Your deals are stalling because prospects don't trust you yet.

Not because your product doesn't work. Not because your pricing is wrong. But because nothing in your marketing or sales process built the foundation of trust needed to close.

The Five-Minute Trust Audit

Run these five tests right now. Each one reveals a specific trust gap in your go-to-market approach.

Test 1: The Reference Question

Ask your sales team: "When prospects ask for references, what do they actually want to know?"

What you'll hear:

"Do you have customers like us?"
"Will you actually be there when things break?"
"What do other CISOs say about you?"

What this reveals: If your marketing doesn't proactively address these questions, you're making every prospect ask them individually. That's friction. Friction kills deals.

The trust gap: Your marketing focuses on features and benefits. Prospects want proof you'll show up.

Test 2: The Competitor Test

Ask: "When we lose deals, what does the winner have that we don't?"

If the answer is: "Better features" or "Lower price" → You're probably wrong. That's just what the prospect told you.

Dig deeper: "Do customers ever mention the competitor's brand or reputation when they choose them?"

What this reveals: Most cybersecurity deals go to the vendor the CISO already trusts or has heard good things about. If you're losing to name recognition, your trust problem is a brand problem.

The trust gap: You're competing on product when the decision is being made on reputation.

Test 3: The Language Test

Pull up three pieces of your marketing content (website, case study, sales deck).

Ask: "Could our competitor have written this exact same content by changing the logo and company name?"

If yes: Your content isn't building trust. It's generic. CISOs read it and think "I've seen this before from ten other vendors."

What this reveals: Trust comes from demonstrating you understand their specific situation. Generic content doesn't do that.

The trust gap: You're creating content that scales (AI-generated, templated) instead of content that builds credibility (specific, expert-driven).

Test 4: The Sales Adoption Test

Ask your sales team: "What marketing materials do you actually use in conversations with prospects?"

What you'll often hear:

"I use my own deck"
"The case studies don't demonstrate value"
"The website doesn't help me"

What this reveals: If sales isn't using your marketing materials, it's not because they're difficult. It's because the materials don't address what prospects actually care about.

The trust gap: Marketing is creating what they think should work. Sales knows what actually works. And nobody's connecting those dots.

Test 5: The Timeline Test

Track your last 10 closed deals:

How long from first touch to closed deal?
Where did deals slow down?
What questions came up repeatedly?

What you'll often find: Deals slow when prospects need to validate you with their peers, get internal buy-in, or understand if you're credible.

What this reveals: Delay can represent a trust gap. If deals consistently slow at "we need to review internally," that's code for "we need to validate you're legitimate."

The trust gap: You haven't proactively built the credibility needed to move fast.

What These Tests Reveal

If you failed multiple tests, here's what's happening:

Your marketing is optimized for volume, not trust.

You're generating leads, but not building the foundation prospects need to buy. Every prospect has to independently validate you, which slows everything down.

Your sales and marketing aren't aligned on what actually closes deals.

Sales knows what prospects care about (references, reputation, proof). Marketing is creating content about features and benefits.

You're competing in the wrong arena.

You're trying to win on product differentiation. Your prospects are buying based on trust and word-of-mouth.

What Your Competitors Are Doing Differently

While you're focused on lead volume, your competitors are:

Building systematic trust at scale: Their content answers the validation questions before prospects ask. Their case studies focus on relationships, not just results.

Creating customers who refer: Not through referral programs, but by delivering experiences worth talking about.

Showing up where trust gets built: CISO peer groups, regional conferences, community contributions. Not to sell, but to be known.

Making it easy for prospects to validate them: Public customer stories, accessible expertise, visible reputation in the market.

The Hard Question

Are you measuring leads generated? Or trust built?

Because in cybersecurity, you need both. But if you're only measuring the first, you'll keep wondering why your close rates stay flat.

What to Do About It

Fix Test 1 failures: Document the real questions prospects ask. Answer them in your marketing before they have to ask.

Fix Test 2 failures: Stop competing on features. Start building brand and reputation that CISOs hear about.

Fix Test 3 failures: Create content that demonstrates specific expertise. Let subject matter experts lead, not AI tools.

Fix Test 4 failures: Sit with sales. Find out what actually works in conversations. Make more of that.

Fix Test 5 failures: Map where deals slow. Proactively address those validation points earlier in the process.

The Bottom Line

Your deals aren't stalling because prospects don't understand your product.

They're stalling because they don't trust you yet.

And trust can't be generated by AI, automated in a workflow, or optimized through A/B testing.

Trust gets built through:

Demonstrating real expertise
Creating customer experiences worth talking about
Showing up consistently where your market pays attention
Making it easy for prospects to validate you

Run these five tests. Find your trust gaps. Then fix them.

Coming up: Your sales calls are your best marketing (and you're wasting them). How to extract insights from conversations and build scalable systems from what's actually working.

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:** Sales Process Audit, Deal Velocity, Trust Building, B2B Sales, Marketing-Sales Alignment, Competitive Analysis, Sales Enablement, Trust Gaps, Sales Diagnostics, Deal Stalling