Turning “No” Into “Yes”

Greg shared some incredible stories about turning lost deals into long-term wins. One example involved a client who had already rejected his proposal and chosen a competitor.

“The board had decided to go with another vendor,” Greg told me. “But I asked one simple question: Why don’t you test our product on your new cloud platform?”

That pilot eventually became a 25-year partnership.

Another time, Greg met with a client who told him they’d thrown his proposal in the bin. Instead of walking away, he asked questions to understand their real objections.

“It wasn’t about the technology—they liked it. The issue was price,”

he explained. By offering a low-cost pilot, he turned the rejection into a rollout spanning 80 properties and a partnership lasting two decades.

What I learned here is the importance of diagnosing the real issue. Often, the objections we hear—like pricing or features—mask deeper concerns. Greg’s ability to ask the right questions unlocked opportunities that others might have missed.

Competing as the Underdog

XN Global often competes against massive companies with bigger budgets and resources. Greg admitted,

“We’re almost always the underdog. But being smaller has advantages—we’re faster, more flexible, and can customize solutions in ways larger companies can’t.”

For example, he described a project where his company was building a system for a student housing provider. They went from 17th place in the first round of an RFP to winning the deal.

“We focused on what the client really needed, and we showed them how we could deliver quickly—even though parts of the system didn’t exist yet,” he said.

As someone running a smaller agency, this resonated with me deeply. Being the underdog isn’t a disadvantage if you know how to position your strengths. Speed, adaptability, and personal attention can be real differentiators.

Focus Beats Numbers

One piece of Greg’s advice that I’ve already started applying is the power of focus.

“I’ve never believed in the idea that sales is a numbers game,” he said.

“Early in my career, I’d have a hundred quotes out and close none of them. When I shifted my approach to focus on one deal at a time, everything changed.”

Greg compared it to a lion hunting a zebra:

“The lion that catches its prey doesn’t chase the whole herd. It focuses on one zebra and commits everything to catching it.”

This approach makes so much sense. In sales, spreading yourself too thin leads to shallow efforts. By committing fully to one deal, you can dig deeper, ask better questions, and show the client you genuinely understand their needs.

Modern Marketing vs. Personal Selling

Greg was candid about his views on modern marketing tactics.

“I delete most of the emails I get—click campaigns, SEO efforts, all of it. They don’t work for me,” he said.

Instead, his success comes from personal connections.

One story stood out: Greg was having tea with someone in China when he casually asked about their challenges. That conversation led to a $500,000 deal.

“People-to-people selling is what works. It’s about listening, asking good questions, and building trust,” he said.

I couldn’t agree more. Modern marketing is great for building awareness, but in enterprise sales, nothing beats real conversations. People buy from people, not just products.

Advice for Scaling Sales

When I asked Greg about scaling sales beyond the founder, his advice was clear:

1. Learn by Doing: “Enterprise sales is an apprenticeship. You learn by watching experienced salespeople in action and practicing until you get it right.”

2. Know the Product: “You can’t sell what you don’t understand. You need to know not just what the product does but how it solves real problems.”

3. Understand the Client: “Classify your clients into types—whether they’ve outgrown their current solution, are stuck in a bad system, or are chasing a dream solution. Once you know their pain points, you can address them effectively.”

He also emphasized the importance of honesty.

“If you don’t have a feature, say so. But explain how you’d approach delivering it. Clients appreciate honesty and creativity over empty promises.”

Final Thoughts

What struck me most about Greg’s approach is how personal it is. He doesn’t rely on flashy presentations or generic pitches. Instead, he listens, diagnoses, and builds trust.

For those of us running businesses, Greg’s lessons are powerful reminders that being small doesn’t mean you’re at a disadvantage. If anything, it allows you to be faster, more adaptable, and more focused.

If you’re navigating tough sales challenges, take a page from Greg’s playbook:

• Dig into the client’s real pain points.

• Focus your energy on closing one deal at a time.

• Build relationships that go beyond the transaction.

And, as Greg says, never count yourself out. Even when it feels like the deal is lost, there’s often a way forward if you’re willing to ask the right questions.

I’d love to hear your thoughts. Have you had any “impossible” sales moments?

What’s worked for you? email me at artur@scale-wise.com