podcast · sales mindset · sales skills ·Jul 30, 2026

How to Stay Ahead in 2026 | Jacquelyn Goldberg

In Episode 190, Drewbie sits down with Jacquelyn Goldberg to talk about persistence, self-awareness and AI in sales.

Jacquelyn tells the story of flying to Miami knowing she'd lost the deal, then winning it back by showing up, staying curious and asking the right questions. The episode covers self-doubt and building real relationships.

They also talk about AI, why it won't replace great salespeople, and how top performers can use it to gain an edge.

If you've ever struggled with confidence, balance, or adapting to change in sales—this one's for you.

What You'll Learn

Why showing up (even after a "no") can completely change the outcome
How asking the right questions beats pitching every time
The real reason most salespeople hold themselves back
Simple practices to get out of your own head and perform better
Why sales success is more like farming than hunting
How AI is changing sales, and how to stay ahead
Why human connection will always win in sales

Key Takeaways

You have nothing to lose when a deal is already gone—so go all in
Self-awareness is your biggest advantage (or your biggest obstacle)
Journaling + coaching = clarity and growth
Balance is intentional
AI will expose bad salespeople
The best salespeople use AI as a tool

Memorable Moments

Turning a lost deal into a win by showing up in person
Cold calling at 15 years old and closing high-ticket retail sales
Realizing sales was a calling
Admitting that being your own worst critic can hold you back
Breaking down the reality of "balance" in a high-performance career
The truth about AI and why human connection still dominates

Connect with Jacquelyn

LinkedIn: Jacquelyn Goldberg
Website: https://www.unframe.ai/

Call The Damn Leads

"By sales professionals, for sales professionals — Tales of your wildest sales stories and tactics to succeed in your sales career across various industries."

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More on this: Jorge Chavez on why closing shouldn't be the goal. New here? Start with what Call The Damn Leads is.

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Frequently Asked Questions

Is it worth showing up after you've already lost the deal?

Jacquelyn flew to Miami knowing the deal was gone, and won it back. Her logic: you have nothing to lose when it's already lost, so go all in. Show up, ask better questions, be present in the room. Most people quietly disappear after a no, which is exactly why showing up anyway lands so hard.

Is AI going to replace salespeople?

No, and Jacquelyn is blunt about why. AI is good at the work around the sale: research, notes, follow-up drafts, prep. It is not good at sitting across from someone who is nervous about spending money. The reps who win are the ones using it to buy back time, then spending that time on human contact.

Why is sales more like farming than hunting?

Because the deals worth having take seasons, not afternoons. Hunting is one kill and back to zero. Farming is planting, tending, and harvesting on a cycle you trust. Her point is that consistency beats intensity, and the reps who stay in touch through the quiet months are the ones with a pipeline when everyone else is starting from scratch.