Gems From "Jerry" The Mentor

Before we begin: Welcome (again) to new subscribers & thank you to the OGs for sticking with me during this rebrand. To attract the more new subs, I am writing new content based off my experience and lessons learned through the years. I’ll slowly copy/paste some of my best performing articles from the previous newsletter as well.

How Jerry Became a Consistent $2M+ YoY Sales Machine

I want to tell you about Jerry.

He’s the guy every sales rep dreams of having:

• Consistent President's Club winner.

• A 10x biller - always billing $2M+ when I worked with him.

• He makes everyone around him better (both recruiting and sales) just like a great quarterback or point guard.

But what makes Jerry exceptional isn’t just the accolades. It’s how he works.

While others are throwing sh*t at the wall and hoping it sticks, Jerry’s running a system—a proven playbook that keeps him outperforming the competition year after year.

Here’s what I learned from shadowing Jerry and breaking down his $2M success:

1. Be a Relationship Builder, Not a Transactional Closer

Jerry doesn’t “sell.” He solves problems.

He doesn’t walk into meetings armed with a pitch deck; he walks in with questions. His superpower? Listening—like, really listening.

I had the privilege of sitting next to him when I started my career, and one of his favorite lines to both current & new clients:

By the time he’s done, his clients don’t just see Jerry as a vendor—they see him as a partner. A true extension of their hiring team looking out for their best interest.

That’s why they call him back for more business.

Jerry’s Rule #1:
If you’re focused on the sale, you’ll win once.
If you’re focused on the relationship, you’ll win for life.

2. Lead Generation Is an Art (Not a Grind)

Ever wonder why Jerry never looks frazzled, even when the quarter’s ending?

It’s because Jerry doesn’t chase leads—he attracts them.

• He spends 20 minutes a day researching high-potential prospects.

• His outreach? Custom. Personal. No cookie-cutter templates.

• And he knows how to find “warm doors” by leveraging introductions from his existing network.

• He leads with the number 1 indisputable value prop: the MPC

Most reps are stuck in “spray and pray” mode. Not Jerry. He’s precise, a sniper, and it shows.

3. The Science of Closing Without Pressure

Jerry’s secret weapon in negotiations?

Empathy.

When you negotiate like Jerry, you don’t push. You guide.

Here’s his mindset shift:

By the time Jerry presents a deal, the client’s already sold on the idea. They’re just ironing out the details.

That’s why Jerry’s close rate is absurdly high.

4. Master Your Calendar Like Your Income Depends On It (Because It Does)

Jerry blocks his time ruthlessly.

• Mornings? Lead generation and high-value outreach.

• Afternoons? Client follow-ups and relationship-building.

• Evenings? Time to reflect and fine-tune his process.

• Follow Ups? He’s doing it when you’re taking a break, before the day starts, during lunch, and after hours when clients are more likely to be available.

And he’s the king of delegation. If it doesn’t directly impact his revenue, someone else handles it.

Takeaway:
Every minute Jerry spends on low-priority tasks is a minute he’s not making money.

5. Resilience = The Ultimate X Factor

Jerry wasn’t born a sales phenom. Early in his career, he missed quotas. Faced rejection. Burned out.

This may potentially dox the person I’m talking about, but he’s had to rebuild his book of business three separate times.

His first client, had I believe 40-50 billables, went belly under during the financial crisis of 08/09. His second client, for compliance reasons, kicked him off the vendor list (had over 100 billables). He left our company for personal reasons, always had 80+ billables. And at his most recent company, he hit 120+ at his peak.

But here’s the thing: He learned from every single misstep.

When others got discouraged, Jerry asked himself,
“What can I do better next time?”

That mindset—the ability to adapt and grow—is what separates the good from the great.

Why Jerry Wins (And You Can, Too)

Jerry’s not a unicorn. He’s just a guy with a system.

The relationship-first mindset.
The precision in lead gen.
The empathy in negotiations.
The calendar discipline.
The resilience to keep going when it’s hard.

You can build these habits, too.

Start by asking yourself:

• Am I prioritizing relationships or transactions?

• Is my outreach thoughtful—or robotic?

• Do I own my calendar—or does it own me?

The road to $2.4M in billings doesn’t happen overnight. But if you take it one step at a time, you might just find yourself on stage at the next President’s Club dinner.

Let’s make it happen.