How to Stay Ahead in 2026 | Jacquelyn Goldberg

In Episode 190, Drewbie sits down with Jacquelyn Goldberg to unpack the power of persistence, self-awareness, and the evolving role of AI in sales.

Jacquelyn shares a powerful story of flying to Miami knowing she lost the deal—only to win it back through presence, curiosity, and strategic questioning. From navigating self-doubt to building authentic relationships, this episode is packed with real-world insights for sales professionals at every level.

They also dive deep into AI's impact on the industry, why it won't replace great salespeople, and how top performers can leverage 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 the game—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 isn't perfect—it's intentional

• AI won't replace salespeople—but it will expose bad ones

• The best salespeople use AI as a tool, not a crutch

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 wasn't a choice—it 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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