There’s Always a Way: How Creative Influence Turned “No Value in Meeting You” Into an Eight-Figure Win

Every seller has that one story — the one meeting that felt impossible, the one gatekeeper that seemed impenetrable, the one deal that defined the entire year. For me, this is that story. And it began with the seven words no salesperson wants to hear:

“I don’t see value in meeting with you.”

Years ago, I was staring down a massive security opportunity that had the power to make or break my year. It was the deal. If we won it, we’d move markets. If we missed it, the year would fall short. The only path forward required engagement with the customer’s Chief Security Officer — someone widely respected in the industry, fiercely loyal to their existing vendors, and completely uninterested in our solutions.

The first outreach attempts failed. The usual angles fell flat. Nothing resonated. And that’s when I realized something important: if the standard playbook doesn’t work, you don’t abandon the game. You rewrite the playbook.

Understanding the Blocker

I started where all great influence starts: research.

This CSO had a significant public presence. They posted regularly on LinkedIn, spoke on podcasts, and openly positioned themselves as a security evangelist. They weren’t just a technical leader; they were a thought leader. They valued ideas, point-of-view, peer dialogue, and executive-level conversations.

And that was the unlock.

This individual was never going to entertain a seller-to-executive conversation. But they would consider a thought-leader-to-thought-leader exchange.

That meant I needed to elevate the engagement. I needed to meet them where they operated. And I needed to create value that aligned with their brand, their identity, and their motivations.

Reframing the Meeting

So I went internal and called in a favor.

I identified a senior leader within our organization — someone with the credibility, background, and presence that matched the CSO’s level of expertise. Someone who could sit across from them and speak the language of security strategy, compliance, risk, and enterprise protection like a peer.

And yes, I elevated the way I introduced them. Titles matter in these moments, not because we’re trying to embellish anything, but because the external world often requires different framing than our internal vernacular. Inside the company, we use one set of labels. Outside, sometimes the value is better understood with another.

Once I had the right person identified, I crafted a message that changed the entire trajectory of this opportunity.

I acknowledged the CSO’s platform. I recognized their influence. I positioned the meeting as a CISO-to-CISO mindshare session — a chance to connect on industry shifts, compliance roadmaps, emerging business risks, and strategic insights. I included profiles and bios of the experts who would join the conversation. I made it clear that this was not a product pitch. It was an opportunity to exchange ideas among security leaders.

And then I asked for availability over the next couple of weeks.

The Turning Point

I sent that message at 9:14 a.m.

Later that same day, I received the reply:

“Flattery can get you everywhere. I’d be happy to meet.”

That was the moment the door cracked open. From there, the relationship formed naturally. We collaborated. We listened. We built rapport. We created a shared understanding of what mattered, what needed solving, and what future-state security should look like for their organization.

Within eight months, we closed an eight-figure deal.

It became one of the most significant wins of my career, and I was honored with the biggest award in the company.

But the story isn’t about the award. It’s about what it took to earn the meeting that made the award possible.

The Lesson Behind the Story

This experience taught me several powerful truths that I’ve never forgotten:

People don’t reject you. They reject the version of you that doesn’t yet resonate with their world.

When someone says “I don’t see value in meeting,” they’re not saying value doesn’t exist. They’re saying you haven’t shown it yet.

The most important skill in sales isn’t pitching. It’s value creation.

Not generic value. Not recycled value. Not slideware value.

But highly specific, deeply personal, uniquely tailored value — the kind that resonates with the executive’s identity, challenges, priorities, and thought leadership.

And more than anything, it’s this:

There is always a way.

The door is never fully closed. The challenge is rarely insurmountable. The obstacle is only a signal that the path you attempted is not the right one.

If you can step back, learn from it, and reshape your approach, you’ll be shocked at what becomes possible.

Final Thoughts

Deals don’t materialize because of clever features or polished decks. They materialize because of relationships, influence, creative thinking, and the courage to approach things differently when the usual approaches fail.

If you’re staring at an impossible meeting right now, remember this:

There’s always an angle.
There’s always a way in.
There’s always a path forward.

You just have to find it.

Happy selling.