Why Your Sales Team Sounds Like a Robot Having a Stroke (And How One CMO Fixed It By Actually Listening)

Snap out of it: Your sales pitch probably sucks.

And I know this because last week I sat down with Sebastian Pistritto—a four-time CMO who's scaled more SaaS companies than you've had awkward Zoom calls—and he basically told me that 90% of B2B companies are out here selling like it's 1997.

Here's what's happening: Your sales team is walking into conversations with healthcare executives, dropping feature bombs like they're at a tech demo, completely oblivious to the fact that the person across from them doesn't give a single shaet about your "proprietary algorithm" or your "seamless integration capabilities."

They care about one thing: Does this solve my actual problem?

The $122K Mistake Everyone's Making

Sebastien told me about a company that was trying to pivot from one vertical to another. Classic move, right? They had this killer platform that delivered operational efficiencies and compliance benefits.

So they walked into a new industry and started preaching the gospel of operational efficiency.

Crickets.

Turns out? This new industry didn't see it as an operational efficiency problem. They saw it as a "holy shaet we have too many people on payroll and it's destroying our margins" problem.

Same technology. Completely different language.

Once they figured this out and stopped talking about their product like a spec sheet from Best Buy?

• Sales cycle: 9 months → 4 months

• Average deal size: $28K → $150K

Yeah. You read that right. They 5x'd their deal size by simply speaking human.

The Psychology You're Ignoring (At Your Own Expense)

Here's the thing that blew my mind: Sebastien breaks down organizations into three tiers—the C-suite, the directors, and the workers. And guess what? They all see the problem completely differently.

• CEO: "I want market share. Show me ROI and I'll spend."

• Director: "I have a fixed budget and it's already gone. Come back never."

• Worker: "My 8-hour shift is now 12 hours and I'm drowning."

Same company. Same problem. Three totally different conversations.

And your sales team is probably using the exact same pitch for all three.

That's not a strategy. That's laziness dressed up as efficiency.

The Magic Word That Changes Everything

Want to know Sebastien's secret weapon? It's not a fancy CRM. It's not AI. It's not even a slick deck.

It's the word "why."

That's it. That's the tweet.

"Why are you looking for this solution?" "Why are you doing it this way today?" "Why now?"

Here's what happens when you actually ask these questions instead of vomiting features:

1. You stop being a vendor. You become a trusted advisor.

2. They stop defending their budget. They start problem-solving with you.

3. You build actual trust. Not the LinkedIn "let's connect" kind. Real trust.

Sebastien calls it meeting people where they are. I call it not being a tone-deaf robot who memorized a script.

The Reflection Move That Seals the Deal

After you've done your discovery (you know, actually listened), here's the play:

"Karl, let me make sure I understand: You want to reduce costs, you've got too many people working on this, your old process is broken, and if you don't fix it soon it's going to impact the business. Did I get that right?"

Boom.

Now they feel understood. Now they feel validated. Now you're not just another vendor trying to hit quota—you're a human being who actually gets their pain.

And THEN—only then—do you talk about your solution. But here's the kicker: You only talk about the specific features that address their specific problems.

Not every bell and whistle. Not your full product roadmap. Just the stuff that matters to them, right now, in this moment.

Why This Matters for Your Scaling Nightmare

If you're in health tech, medtech, or SaaS right now, you know the game has changed. Budgets are tighter. Decision cycles are longer. Your prospects are more skeptical than ever.

You can't brute-force your way to growth anymore.

The companies winning right now? They're the ones building authentic client connections. They're humanizing business relationships in a world that's increasingly transactional and AI-automated.

They're doing H2H (human-to-human) instead of pretending B2B is somehow exempt from basic human psychology.

The Bottom Line

Sebastien's approach isn't rocket science. It's just forgotten science.

Ask why. Listen. Reflect. Present solutions that actually match their problems. And for the love of all that is holy, stop leading with your product's technical specs.

Your prospects aren't buying technology. They're buying outcomes. They're buying solutions to problems that are keeping them up at night. They're buying the feeling of being understood.

And if you can deliver that? You'll cut your sales cycle in half and multiply your deal size while everyone else is still wondering why their conversion rates look like a sad PowerPoint chart.

Want to hear the full conversation? Check out Episode 45 of The Human Connection Podcast where Sebastian breaks down exactly how to transform your customer acquisition process—without sounding like a robot having a stroke.

P.S. If your sales team is still opening calls with "Let me tell you about our platform's capabilities," I'm begging you: send them this episode. Your CFO will thank you. Your prospects will thank you. Hell, even your sales team will thank you once they stop getting ghosted after demo calls. The only relationships that matter in business are human ones—even if your buyer is an "enterprise decision-maker" with a fancy title. They're still just a person trying not to screw up their next move. Treat them like one.

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H, human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.