Every era in sales has its defining challenge. Today’s is simple to describe but hard to master: we’re selling in an AI-everywhere world where buyers are flooded with noise, automation, and cold outreach. Products are easier to compare, competitors are faster to copy, and customers are more skeptical than ever.

So how do you stand out? You don’t lead with tech. You lead with trust, orchestration, and precision—powered by resourcefulness and relationships.

From Lone-Wolf Closer to Chief Orchestrator

Early in my career, I cut my teeth in call centers selling DSL lines and long-distance plans. It was a one-call-close environment—you had maybe 90 seconds to build rapport, create urgency, and close. Fast-forward to today: I’m orchestrating multi-year, multi-million-dollar SaaS transformations where 80 people might touch a single project.

The skill set is night and day different. Back then, it was about persuasion. Now, it’s about collaboration and choreography. You’re no longer the hero of the sale—you’re the conductor of a complex orchestra where everyone’s playing a part in the customer’s outcome.

That means learning to love internal selling, to manage 80 personalities, and to make the customer—not yourself—the star of the story.

The Three Traits That Compound Wins

If I had to reduce 25 years of lessons into three words, they’d be these: Networking. Resourcefulness. Resilience.

Networking: Your network is your net worth. Relationships beget deals. Every major win in my career traces back to a person, not a product. I’ve never once hit quota by staring at a number—I’ve hit it by obsessing over people and process.

Resourcefulness: Sometimes you’re out of budget, out of time, or out of favor. That’s when you get creative. I’ve been told “no funding available” and found a secondary sponsor line inside my company that got me a million-dollar investment approved in 24 hours.

Resilience: You’ll get punched in the mouth. Deals will collapse. Champions will leave. But like a pro athlete, you learn, you adjust, and you move forward. Each hit refines your instincts and sharpens your edge.

Earning the Right to Advise

Here’s the truth: buyers don’t care what you sell until you’ve proven you care about what they care about.

I’ve never led with product. I lead with purpose—their purpose. I want to know what their board cares about, what their KPIs are, what they want their legacy to be. Once you understand that, the sales conversation becomes a co-authored plan instead of a pitch.

Executives don’t fear missing out—they fear messing up. Your job is to de-risk their decision.

Show them a safe, credible, step-by-step path to value. Start with one high-impact use case. Deliver a win. Then scale. That’s how you create velocity.

AI: The Great Differentiator—Or the Great Equalizer

Let’s be real: AI is the buzzword of our time, but most organizations are still figuring out what it means for them. Some say they’re “not ready.” Others are all-in and overwhelmed by choice.

When I hear “we’re not ready,” I respectfully challenge it. Because usually, they are—they just don’t know where to start. I’ll ask:

What process is consuming the most time?Where are decisions bottlenecked?What information do your people need but can’t access fast enough?

Those are AI conversations. AI isn’t about replacing people; it’s about freeing them to do their best work.

And when everyone’s claiming to have “the best AI,” differentiation doesn’t come from the tech—it comes from how you de-risk, integrate, and humanize it.

My Own AI Playbook

I practice what I preach. AI helps me draft one-on-one agendas, write morning notes to my team, craft executive emails, and summarize meeting notes. It used to take me an hour to write my monthly newsletter. Now it takes five minutes.

But here’s the key: I still add my voice, my story, my authenticity. Technology should scale you, not replace you.

Building the Moneyball Engine

Over a decade ago, I built what I call my Moneyball prospecting engine. It’s fueled by one philosophy: Quality message × Quantity of outreach × Consistency of execution.

I use LinkedIn Sales Navigator religiously. I reach out to hundreds of executives across different lines of business—finance, HR, operations, marketing—because I know the first “yes” often comes from the least obvious place.

My biggest deal at Microsoft started with one cold LinkedIn message. Two years later, it became a nine-figure partnership.

That doesn’t happen by luck. It happens by disciplined repetition and personalization at scale.

Orchestrating the V-Team

A single seller can’t do this alone. In one major account, I had over 80 people touching the customer. Different incentives. Different bosses. Different noise.

I learned early that everyone’s being coached by someone else—and often to do conflicting things. The only way to align is to connect on purpose.

I created a system called Plays That Get You Paid. I’d meet with every specialist, engineer, and partner and ask, “Which conversations make you money?” Then I’d go create those conversations for them.

When you generate “Glengarry” leads that tie directly to their paycheck, collaboration becomes effortless.

The Executive Playbook

If you want to reach executives, stop waiting for permission.

Procurement might gatekeep. IT might push back. Respect them—but reach higher. Executives are desperate for insights that make them look smart and safe.

One of my biggest wins came from a CIO who initially refused to meet me. He said, “I don’t talk to vendors.” I went to the board, CFO, and CEO, learned what he really cared about, and forced a meeting. I told him, “Give me one project to prove we can help you. If I fail, you’ll never hear from me again.”

We delivered the win. He still didn’t like me—but we got the deal. Sometimes leadership means being Batman—the hero willing to be the villain to get the job done.

Control the Controllables

The best advice I ever received: Control the controllables.

You can’t control the economy, your manager, or your quota. But you can control your calendar, your cadence, and your composure.

I call it the Balcony View. Picture Superman hovering above the earth, listening for signals. You can’t respond to every cry for help. Choose the right fire to fly toward.

Pin your top priorities: your leader, your directs, your key deals. Everything else is noise.

Challenge Everything Holding You Back

When I started as an account executive, I missed my goal. Zero rewards. Insufficient results. It was humbling.

But that failure became the foundation of everything that came after. I studied what worked, stripped out what didn’t, and built systems that made me unstoppable.

I learned that small tweaks—better questions, tighter discipline, one more connection—create exponential results.

One new conversation can change your year.

The Final Lesson

The worst advice I ever got was “Go sell more of X.” Numbers don’t move people—people move numbers.

The best sellers in the world aren’t the most technical or the most talkative. They’re the ones who care the most, adapt the fastest, and never stop learning.

AI may rewrite the rules of sales, but the core remains the same: Build trust. Solve real problems. Make your customer the hero.

That’s how you win. That’s how you stay unbeatable.

Because in a world of automation, the ultimate differentiator is still you.