They’re Not Buying Your Product.

(Estimated reading time: 10-11 minutes.)

They’re Buying Protection from blame, from friction, from regret.

Over the last 10+ years, I’ve had direct conversations with more than 5,000 prospects, many of them founders, C-levels, or VPs making critical purchasing decisions.

What I thought they cared about (ROI, feature sets, integrations) wasn’t what moved them.

What actually made them buy?
Fear. Risk. Status. Trust.
Not always in that order.

In this newsletter, I’m going to show you the 3 mental triggers that guide most executive-level purchasing decisions and how early-stage founders can build positioning that sells upstream.

This is especially critical if:

• You’re selling B2B, and deals are slowing down

• You’re talking to champions who love your product, but can’t sell it internally

• You want to stop being a "maybe later" and start being a "we need this now"

Let’s dive in.

Mental Trigger 1: "What’s the Cost If I Ignore This?"

Most execs don’t get promoted for saying yes to vendors.

They get promoted for choosing what not to care about.

When they see your cold email, your LinkedIn DM, or your pitch, here’s what runs through their mind:

• Is this a pain I’m willing to defend on next quarter’s roadmap?

• If I ignore this for 6 months, will anything break?

• Is this a strategic risk or just a productivity itch?

If your positioning doesn’t make the risk of inaction feel expensive, it gets buried under a pile of other priorities.

Bad positioning sounds like:

We help teams collaborate better.

Okay, but what happens if I don’t collaborate better? Nothing? Then I’ll ignore it.

Strong positioning sounds like:

Sales teams using [your tool] recover 10 to 15 percent of pipeline lost to misaligned follow-ups and rep handoffs.

Now you’re talking about revenue loss. Not just collaboration. That’s strategic.

Make this shift:

Stop positioning around what your product does.
Start positioning around what breaks if they ignore you.

Mental Trigger 2: "Will This Create Second-Order Work?"

Even if your product is amazing, the exec is asking:

• Who’s going to own this?

• Will this get stuck in legal, security, or IT?

• Will my team quietly hate me for adding another tool to their workflow?

They’re not just buying functionality.
They’re buying the internal story they’ll have to defend if it creates friction.

This is where early-stage founders often lose deals.

Your product may save them time. But if it takes three Slack threads, a security review, a new onboarding doc, and a team Zoom to implement, you’ve created more work than value.

Even worse: if it’s unclear who owns it, no one does.

Positioning Tip:
Bake in zero-friction narratives:

• It works out-of-the-box with your current CRM.

• We’ve built secure-by-default workflows for mid-size GTM teams.

• Onboarding takes under 30 minutes and includes async videos.

• We do the setup for you with one 20-minute call.

You’re not just solving a problem.
You’re neutralizing future objections before they surface.

Mental Trigger 3: "Will This Make Me Look Smart or Exposed?"

Nobody wants to champion a tool that flames out.

Especially not when headcount is tight, budgets are under scrutiny, and every vendor feels like a bet.

Executives ask:

• If this works, who notices?

• If it doesn’t, who blames me?

• Will this age well if we grow, go up-market, or raise?

They don’t just want results.
They want reputation insurance.

If saying yes to your tool feels like a career risk, they’ll stall. Or ghost you. Or kick the can.

But if it feels like a strategic move they can defend, they’ll fight for it internally.

Positioning Tip:
Add social proof that matches their context:

• We’re working with three other Series A SaaS teams with similar funnels.

• We replaced [well-known competitor] at [peer company] and shortened time-to-close by 30 percent.

• Your competitor [X] just rebuilt a similar process in-house. We’ve packaged it for you.

Remember: execs aren’t just buying results.
They’re buying confidence in the future.

Reframing the Role of Positioning

When most founders think about positioning, they think:
How do I sound impressive?

That’s the wrong lens.

The right lens is:
How do I make the buyer feel like saying "no" is the risky move?

That’s when your product goes from interesting to inevitable.

You stop being a tool.
You start being a strategy.

Steal This Cold Email: Positioning That Works on Executives

Here’s a cold email I’ve used (and coached founders to use) that consistently gets real replies and booked calls, not just polite interest.

“Subject: Idea for ProspectCompany – quick question

Hi ,

While exploring ProspectCompany's site, I noticed personalized_findings. (Hope you don’t mind me pointing this out!)

I’m YourName, the founder of YourCompany. We specialize in {one-liner – e.g. "helping B2B software firms improve their sign-up conversion rates"}.

Based on what I saw, I actually have a couple of ideas that might {benefit to prospect – e.g. "increase your trial signups" or "fix that issue easily"}. I even recorded a 3-minute Loom video walking through it – happy to send it over if you’re interested.

Either way, I really admire what you’re building at ProspectCompany. If you’d be open to it, I’d love to hop on a 15-minute call to share those ideas and learn more about your goals.

Thanks, and have a great day!
Your Name
Founder, YourCompany” 

Why It Works:

• Specific, personal hook (not fake-flattery)

• You offer value first (not pitch language)

• You make saying "yes" feel easy

• You remove pressure, but still guide toward a call

Want to make it even softer? Ask for feedback:

Even if we’re not a fit, I’d love to hear your take on what we’re building.

That tells an exec: this person listens, not just pitches.

Final Word: Make Saying "No" Feel Riskier Than Saying "Yes"

Founders love building product.
But buyers don’t fall in love with features.

They fall in love with clarity, certainty, and safety.

Your job isn’t to sound brilliant.
It’s to sound like the safest bet on the table.

So next time you write a headline, design a pitch, or send a cold message, don’t ask:
Does this explain what we do?

Ask:
Does this make ignoring us feel like a risk?

That’s when you stop selling.
And start winning.

Stay sharp. Stay strategic.
- Guillaume