How I Closed $1B From LinkedIn: The Real Social Selling Playbook in the Age of AI

Are you building real relationships in your sales process—or just blasting “pitch slaps” into the void?

If you’re like most, you’ve noticed that the sales world has taken a dangerous detour:

Mass messaging with no relevance

False flattery that’s easy to spot

Cringe-level inauthenticity

And sometimes outright disinformation

We’ve forgotten that all selling is social.

And I’m living proof that when you go the other way—when you lead with value, relationships, and consistency—you don’t just get replies… You get multimillion-dollar deals. Like the $120M+ healthcare transformation I helped lead… starting with a single LinkedIn message.

So grateful to my friend Bill McCormick for our recent conversation where I was able to tell my story.

Nobody Cares About Your Product

I didn’t close that deal because of shiny product brochures or clever features. I closed it because I focused on:

The quality of my message

The quantity of strategic outreach

And the consistency of human connection over two years

That’s it.

No secret sauce. Just a system. A repeatable, scalable, people-first system.

From “Accidental Seller” to Social Selling Evangelist

I didn’t dream of being in sales. I stumbled into it through a friend’s aunt who landed me an interview I wasn’t even qualified for.

I thought it was a customer service job. Turned out it was a call center sales gauntlet. Twelve people started training. Only two made it out. I was one of them—because I had no plan B.

All I had were three things:

I could talk fast.I could type fast.And I listened.

That last one? It’s everything. Listening is what makes you dangerous.

Fast forward to today—I’ve helped generate over $1B in revenue, led enterprise deals through recessions and pandemics, and built the playbook that others now follow.

But the core has never changed:

Relationships.

Process.

Discipline.

The Anatomy of a $120M+ Deal (That Started on LinkedIn)

How do you go from cold outreach to a deal of that magnitude?

It started with a message…

But not just any message. I led with value—not product.

“Here are some resources your team is already entitled to…” “Here’s an insight I noticed from your CEO’s recent interview…” “This might help your team right now—no strings attached.”

That’s how you earn the right to a second date. Not by asking for time. But by giving it.

Then came the outreach…

I didn’t message 5 people. I messaged over 500 directors and above across that one organization.

That’s right. Five. Hundred. Not spam. Strategic. Every message thoughtful. Every one a chance to serve.

Then came the follow-up…

I stayed in touch through:

Executive briefings (even virtual during COVID)Sharing personalized insightsHighlighting ways to eliminate risk and drive outcomesInvolving partners, vendors, and internal experts across security, HR, and nursing

And yes, every single executive they hired during those two years? They were introduced to me and my team. Because we had become the constant—the ground zero for strategic transformation.

AI Is the Accelerator—Not the Answer

Let’s talk about AI.

I use it. Every day. But I don’t rely on it. Here’s what it can (and can’t) do for you:

3 Dangers of AI:Feels robotic and impersonal (unless you finesse it)Makes mistakes (don’t trust it blindly)Turns you into noise if you don’t add the human layer 3 Game-Changing Benefits:Instant research: find executive pain points in secondsConversation companion: real-time prompts during meetingsScale content and follow-ups that still sound like you

Example: I once fed real-time meeting notes into Copilot and got 10 strategic insights to guide the conversation—on the spot.

Would I Do It Differently Today?

With today’s tools—Sales Navigator, Copilot, ChatGPT—I could speed up the same outcome. But the heart of the approach would remain identical:

Listen deeplyKnow their legacy goalsFocus on derisking their decisionStay present for the long game

Want the truth? Most customers aren’t afraid of missing out. They’re afraid of messing up.

So I obsess over how I can be their safest bet—not their flashiest pitch.

Carson’s Selling Playbook

Lead with value, not product

Obsess over process, not quota

Relationships are earned, not assumed

Consistency beats cleverness

Use AI—but make it sound like you

Sell like a human. At scale.

For my entire career and $1B Moneyball sales engine playbook, check out “The Show Must Go On”

What’s Your Next Move?

If you’re still pitch-slapping and waiting for replies, stop. Start listening. Start serving. Start building. And you just might find yourself closing your biggest deal yet.

What’s the most surprising deal you’ve ever closed—and how did the relationship start?

Drop it in the comments.

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