Posts by

Koby Jackson

Founder & CEO Calldrip

Why Replacing Humans with AI Bots Might Hurt Your Business

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Koby Jackson

When it comes to customer engagement, nothing says “we care about you” quite like… replacing every human interaction with an AI bot.

Imagine…..

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Sales Is a Contact Sport: Why Conversations Still Win in the Age of AI

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Koby Jackson

Let’s just say it.

Emails? Basically dead.

SMS? Hanging on by a thread.

And yet… we’re still treating them like the lifeline of modern sales.

Why?

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The $100 Million Lesson: Why AI is Succeeding in Sales (and What We Should Learn From It)

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Koby Jackson

AI doesn’t succeed because it’s smarter than us—it succeeds because it does what we should have been doing all along.

In a recent milestone out of Portugal, an AI sales assistant in a real estate brokerage helped close over $100 million in transactions. Not because it’s flashy. Not because it’s futuristic. But because it followed a few simple, timeless principles that human salespeople often overlook.

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Why Every Sales Pro Needs a Personal Landing Page (and a Human Connection Strategy)

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Koby Jackson

In today’s hyper-connected world, your digital presence speaks before you do. And if you’re in sales—or frankly, any customer-facing role—that presence can make or break your credibility.

So here’s a question worth asking: What’s the first thing a prospect sees when they look you up?

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The Biggest Risk Is Life Itself... So Why Not Go All In?

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Koby Jackson

We don’t like to talk about it much, but let’s be honest:

The biggest risk you’ll ever take is life itself.

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From Sleepless Nights to “Overnight Success”: The Truth They Don’t Tell You

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Koby Jackson

You’ve heard the phrase, “It only took ten years to become an overnight success.” It sounds like a joke, but it’s the lived experience of nearly every entrepreneur I know—including myself.

Before Calldrip gained traction, before people called our approach “innovative,” I was drowning in deadlines, and stress-induced sleepless nights. I was calculating cash flow in my head at 2 a.m. and praying that clients paid before payroll hit. There’s no TED Talk for that part.

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Why We Still Believe in Bootstrapping

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Koby Jackson

There’s nothing quite like the energy of the startup. 

When you’re bootstrapping, every decision matters. Every win feels massive. And every person on the team is rowing in the same direction, not because they were told to—but because they believe in where the boat is going.

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The Disease: Waiting to Follow Up

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Koby Jackson

Across industries, agility and speed are often touted as the keys to success. Yet, a pervasive ailment silently undermines many organizations: the failure to promptly follow up with leads. This "disease"—characterized by hesitation and delayed responses—can be fatal, leading to missed opportunities and, ultimately, business failure. Understanding and addressing this issue is crucial for any business aiming to thrive in a competitive landscape.

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We're Not For Sale

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Koby Jackson

At least once a week, someone reaches out to “see if we’re open to selling.”

We’re not for sale.

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How to use AI within your dealership effectively

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Koby Jackson

In the fast-paced world of automotive retail, one thing is clear—your service department doesn’t sound like your sales department, and your parts team sure doesn’t have the same goals as finance. 

Here's the reality: what gets measured gets improved. But if you’re not measuring the right things for each department, you’re missing the mark - and missing opportunities to coach, optimize, and grow.

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