We Have A Meeting Salespeople Who Swear Close 8% More Deals (Here’s Why)
Salespeople who swear on their calls close 8% more deals. Marketing teams using pink and purple instead of "Series A Blues" get more attention. Companies that avoid pissing anyone off end up exciting no one.
In this episode, we sit down with Udi Ledergor, Chief Evangelist and former CMO at Gong, to unpack the psychology behind courageous marketing, the real impact of AI on sales teams, and why being different beats being better every single time.
Udi reveals how Gong built one of the most recognizable brands in B2B by rejecting best practices, embracing controversy, and creating a culture where teams feel safe to fail. From the drooling bulldog mascot that made enterprise customers angry, to the viral research on swearing in sales calls, to the plain-text email that generated 700 event registrations in hours—this is a masterclass in standing out in a sea of sameness.
We also dive deep into AI: what it can actually do right now, what it can't, and why the creators of ChatGPT don't use ChatGPT to run their revenue teams. Spoiler: AI isn't coming for your job. But salespeople who know how to use AI are coming for the jobs of those who don't.
What You'll Learn:
Why swearing on sales calls increases win rates by 8%
The danger of "best practices" and why boring is the biggest risk in B2B marketing
How to build a brand that polarizes—without crossing the line
The two buckets of AI: what it can automate vs. what it can guide you on
Why OpenAI and Anthropic use Gong to run their revenue teams (and what that tells you about generic LLMs)
The plain-text email experiment that got 700 event sign-ups in hours
How to create psychological safety on your team so they take risks and do their best work
Why indifference is worse than hate when it comes to your messaging
From privacy policy emails that went viral, to bulldogs on login screens, to the Starburst logo that refused to fit neatly into a square, this episode will change how you think about marketing, sales, and standing out in 2026.
If your brand feels invisible, your messaging feels safe, or your team feels stuck playing by the rules everyone else is playing by, this conversation will give you permission to break free.
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About the Guest:
Udi Ledergor is Chief Evangelist and former CMO at Gong, and author of the bestselling book Courageous Marketing: How to Take the Boring Out of B2B. He's known for building bold, unconventional marketing teams and helping sales leaders understand how AI is transforming their world.
Find Udi on LinkedIn and grab his book wherever books are sold.
Chapters:
00:00 Salespeople Who Swear Close 8% More Deals: The Research That Went Viral
02:15 Who Is Udi Ledergor: From Gong CMO to Chief Evangelist
04:30 Courageous Marketing: Why Different Beats Better Every Time
08:12 The Series A Blues Problem: How Gong Chose Pink and Purple
11:45 The Drooling Bulldog: When Enterprise Customers Hated the Brand
15:20 How to Be Polarizing Without Crossing the Line
19:03 The Plain-Text Email That Got 700 Event Registrations in Hours
23:47 AI vs Automation: What's Actually New and What's Just Rebranded
28:34 The Two Buckets of AI: Automation and Guidance
32:19 Why OpenAI Uses Gong to Run Their Revenue Team
36:55 Are We Losing Critical Thinking by Outsourcing to AI?
41:28 Building Courageous Teams: Psychological Safety and Process Accountability
47:12 The Privacy Policy Email That Went Viral on Twitter
50:45 One Question to Ask Yourself: How Can You Break Away From Boring Practices?
#CourageousMarketing #UdiLedergor #Gong #SalesPsychology #AIinSales #B2BMarketing #WeHaveAMeeting