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20 Years in Sales: What’s Changed—and What Hasn’t

2025 marks my 20th year in the sales and sales training industry—a milestone that’s made me reflect on how far the profession has come. Over two decades, I’ve seen sales transform in dramatic ways, shaped by technology, shifting buyer behavior, and evolving business models. And yet, despite all the change, some fundamentals remain exactly the same.

I started my career in field sales. Outbound was the name of the game, and customer data lived on handwritten index cards, carefully filed in a bulky plastic box. My first job as a sales engineer? I had a Nokia 3310, a notepad, and a pen. That was it. No CRM, no automation tools, no AI—just conversations, hustle, and handwritten notes.

As my career evolved, so did the industry. I moved into inside sales just as inbound strategies gained momentum. The rise of digital tools changed everything—from how we communicate with prospects to how we track, manage, and close deals. And now, as AI becomes an integral part of the sales stack, we’re entering yet another new chapter.

But here’s what hasn’t changed—and likely never will:

  • Sales still boils down to three core skills: building a pipeline, converting it, and driving revenue. Average reps are good at one. Good reps master two. Great reps nail all three.

  • Pipeline beats everything. Salespeople who consistently generate opportunities outperform even the best closers. No pipeline, no deals—no matter how smooth your pitch is.

  • Leadership mentality matters. The best salespeople lead the conversation. They create momentum, guide the buyer, and shape outcomes. Sales is leadership in action.

Two decades in, I’m more convinced than ever: tools change, tactics evolve, but the essence of sales remains. What other timeless fundamentals would you add to the list?