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I Got Punched for a Living: Why Cold Calling Isn’t Scary

I Got Punched for a Living: Why Cold Calling Isn’t Scary



Cold calling terrifies most salespeople more than losing their biggest account. The rejection. The hang-ups. The voice telling you that you're bothering people who don't want to hear from you. Befor…


Published on 1 month, 2 weeks ago

Building Pipeline From Zero as a First Time Sales Hire (Ask Jeb)

Building Pipeline From Zero as a First Time Sales Hire (Ask Jeb)



Here's a question that keeps startup founders up at night: How does a first sales hire build pipeline and prospect effectively when there's zero technology, no tools, and absolutely no data resources…


Published on 1 month, 2 weeks ago

Thinking Time (Money Monday)

Thinking Time (Money Monday)



Cicero once said, "Cultivation of the mind is as necessary as food to the body." Sales is fundamentally a mental game. Your capacity for understanding your prospects at a deeper level and developing…


Published on 1 month, 3 weeks ago

How a Poor Sales Meeting Strategy Kills Win Rates

How a Poor Sales Meeting Strategy Kills Win Rates



Most salespeople lose a sales meeting before they ever open their mouth. They show up with decks of slides, lists of discovery questions, or AI-generated talking points, thinking preparation is about…


Published on 1 month, 3 weeks ago

How to Start Using AI in Sales (Ask Jeb)

How to Start Using AI in Sales (Ask Jeb)



You know AI is transforming sales, everyone's talking about it, but you're still staring at ChatGPT like it's some mysterious black box, wondering what magical question you should type in first. That…


Published on 1 month, 3 weeks ago

Welcome to Grind Season (Money Monday)

Welcome to Grind Season (Money Monday)



Welcome to Grind Season. This week, we enter the most pivotal period of your entire sales year. From now until mid-December, how you choose to invest your limited time will determine whether you end …


Published on 1 month, 4 weeks ago

How to Uncover Untapped Markets Before Your Competition Does

How to Uncover Untapped Markets Before Your Competition Does



Most salespeople waste their careers fighting over the same crowded prospects. Meanwhile, untapped markets are sitting in plain sight. These are the industries, segments, and territories your competi…


Published on 2 months ago

Sales Prospecting Sequences and ZoomInfo: Buy or Die Without Burning Bridges (Ask Jeb)

Sales Prospecting Sequences and ZoomInfo: Buy or Die Without Burning Bridges (Ask Jeb)



Here's a question that'll keep you up at night: What do you do when you believe in "buy or die" but you're terrified of ruining future opportunities with annoying prospecting sequences? That's exactl…


Published on 2 months ago

How Charlie Kirk Disagreed Is More Important Than What He Believed

How Charlie Kirk Disagreed Is More Important Than What He Believed



I had intended for this Money Monday to be something powerful, a new message that would get you fired up for this week and this season. But last week, while delivering training to an amazing group of…


Published on 2 months ago

The One-Question Revolution That Transforms Sales Discovery

The One-Question Revolution That Transforms Sales Discovery



What if one simple discovery question could close your next big deal? Here’s the one I used: “Tell me what’s going on with your team?” Then I shut up and listened. The buying committee talked, deba…


Published on 2 months, 1 week ago





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