Podcast Summary: The Dave Gerhardt Show – “How to Stand Out in B2B with Udi Ledergor, Chief Evangelist at Gong”

Host: Dave Gerhardt (Exit Five)
Guest: Udi Ledergor (Chief Evangelist, Gong)
Date: December 18, 2025

Episode Overview

This episode features a lively and in-depth conversation between Dave Gerhardt and Udi Ledergor about building iconic, human-centric B2B brands that break the mold of traditional, “boring” marketing. Drawing from Udi’s journey from the first marketer at Gong to CMO and now Chief Evangelist, they explore lessons from Gong’s explosive growth, the importance of courageous marketing, highlights from Udi’s new book Courageous Marketing, and actionable advice for marketers who want to challenge the status quo. The conversation is authentic and energetic, with both speakers emphasizing why bold, differentiated marketing is more important than ever.

Key Themes & Takeaways

1. Udi’s Backstory & Lessons From Gong

• Udi’s Career Journey
  • Grew up in Tel Aviv, initially did not see himself in tech; army service gave him resilience and adaptability.
  • Moved from product management to marketing after recognizing a greater passion for customer engagement.
  • Developed his first VP Marketing role by pitching it internally—lesson in carving your own career path.
• Building Gong
  • Joined as marketer #1; Gong stuck remarkably to its 2015 roadmap, a rare feat in tech.
  • Three reasons Udi chose Gong:
    1. Trust in CEO Amit Bendov’s leadership and vision.
    2. Early raving fan customers (“you don’t usually see that in really early stage companies” [15:25]).
    3. Market fit—loved selling to sales and marketing personas.

“Gong is one of those rare companies … we have not diverted left or right from the 2015 roadmap, and the company’s doing pretty well.” – Udi [14:28]

2. Courageous Marketing: Why B2B Doesn’t Have to Be Boring

The Problem: Defaulting to Consensus

• Many marketers fail because they gravitate toward consensus and safe, “best practice” marketing.
• Playing it safe is actually the riskiest strategy in crowded markets.

“Playing safe is the riskiest strategy of all because you don’t get into trouble immediately for playing it safe ... but you will never cut through the noise.” – Udi [18:19]

The Solution: Be Bold, Be Different

• Example: Gong’s purple/fuchsia brand and bulldog mascot deliberately broke away from B2B’s blue-and-white monotony.
• Visual identity as “lipstick” for a deeper brand personality—start by defining who you are, not just your look.

“We went with fuchsia, pink and purple because I wanted to stand out.” – Udi [19:46]

3. Building Brand Personality Before Visual Identity

• Gong first articulated desired brand traits: mature/authoritative and playful/friendly (not stuffy).
• This alignment ensured congruence between content, voice, and look.

“Some people think that choosing your font is something random. It’s not ... it has to come from a deeper place of who you are.” – Udi [23:13]

4. Punching Above Your Weight: Perception & “Enterprise-Ready” Tactics

Why It Matters

• Startups must look bigger than they are to win enterprise contracts—“perception is reality.”

The Formula

• Choose a “big-company” medium (billboard, podcast, national press).
• Buy the smallest piece of it (regional print ad, one-day billboard).
• Get great photos; amplify obsessively on digital channels.
• Encourage employees to share; amplify “social proof” and team pride.

“I’ve spent $500 buying a Times Square billboard that lights up for two minutes of the day … I don’t care about the random tourists … I care about the 300,000 followers we have on LinkedIn.” – Udi [30:52]

Measuring “Soft ROI”

• Impact isn’t always on a dashboard—brand plays create employee pride, candidate desirability, and sales conversations.
• Use tools (like Gong!) to search for campaign mentions in calls; look for qualitative indicators (social posts, candidate interviews).

“First, the employees who get recognized, they all fly to the nearest billboard … and they are Gongsters for life. Those employees will not leave unless we really F up. So that’s soft ROI number one.” – Udi [32:54]

5. Campaign Highlights & Specific Plays

• Billboards and Out-of-Home:
  • Times Square billboards to celebrate “Outstanding Gongsters” (employee recognition)—now a recurring annual line item.
  • Saster event hijack via one strategic billboard and train wrapping (per Dave’s Drift days).
• Michael Lewis Podcast Sponsorship:
  • Paid appearance for Gong’s CEO; directly tracked 40+ leads mentioning the podcast in initial sales calls.
• Super Bowl Commercial:
  • Conversation mentions and website traffic spikes directly tied to TV ad spend.

“On the week that the episode with my CEO aired, I went into Gong and … the lead said to the salesperson, I heard your CEO on the Michael Lewis podcast. So I went to your website and asked for this demo. How cool is that?” – Udi [36:20]

6. Building a Courageous Marketing Team & Culture

• Psychological Safety:
  • Teams need explicit permission to experiment and occasionally fail.
  • Celebrate experimentation and learning, not just polished outcomes.
• Management’s Role:
  • Push teams for bigger ideas, 10x-thinking, and not incremental improvements.
  • Frame “experiments” in budgets—protects risk-taking from short-term scrutiny.

“You need to create a situation where your team members have the psychological safety to experiment ... they’re actually going to be asked to teach us the learnings from that and then move on to the next thing.” – Udi [42:30]

7. Content Strategy: Quality > Quantity

• Gong Labs publishes original, data-backed research that is immediately actionable by sales professionals.
• One remarkable piece of content is worth more than dozens of generic blog posts.

“If you open a cold call by asking, ‘How have you been?’ you’ll keep people longer on the line than if you ask, ‘How are you?’ … That’s a typical Gong Labs content.” – Udi [46:12]

8. Product-Marketing Alignment

• Alignment between product leadership and marketing is more important than “sales-marketing alignment.”
• Use product data to drive unique, ownable content (e.g., Carta’s Walker Deibel).

“Show me an awesome product, an awesome roadmap, a product leader with vision. That’s the person that I want to pair up with from a marketing standpoint.” – Dave [48:01]

9. The Future: Courageous Marketing in the Age of AI

• AI will eliminate much of the entry/junior-level work, raising the bar for new marketers.
• Courage and creativity will become even more critical as mediocre output proliferates.
• Use AI to clear out the obvious ideas—then go further.

“Courageous marketing is not going away. If anything, it’ll be needed more than ever.” – Udi [50:27]

“The best hack for using [AI] in marketing … ask ChatGPT the top 10 ideas … then take all of those off the table because those are the most obvious ideas that everyone’s already doing.” – Udi [52:12]

Memorable Quotes

• “Playing safe is the riskiest strategy of all because you don’t get into trouble immediately for playing it safe ... you will never cut through the noise.” – Udi [18:19]
• “Gong is one of those rare companies … we have not diverted left or right from the 2015 roadmap.” – Udi [14:28]
• “Visual identity is the lipstick at the end of the process of defining our brand personality.” – Udi [22:47]
• “Perception is reality in our world.” – Udi [28:25]
• “I don’t care about the random tourists ... I care about the 300,000 followers we have on LinkedIn seeing a screenshot of that billboard.” – Udi [30:52]
• “Once you’re spending 2, 5, $10 million a year on media, then you can actually kick in some measurement tools ... But you can’t accurately measure that when you’re spending $10,000.” – Udi [39:37]
• “If you have a company culture where the company’s growing, people love the company, they wanted to show their mom and their cousin … my company’s got this big billboard in Times Square.” – Dave [32:03]
• “At the end of the day, without data, your content is just another opinion. So if you can bring data to the table … that’s how you create the best content marketing.” – Udi [49:56]
• “Courageous marketing is not going away. If anything, it’ll be needed more than ever.” – Udi [50:27]

Notable Timestamps

• [03:08] – Udi’s upbringing, Israeli army, adaptability in life and marketing
• [11:54] – Advice on picking the right company and boss, assessing chaos tolerance
• [14:28] – Gong’s unwavering vision from 2015
• [18:19] – Why “playing it safe” is a marketing death sentence
• [22:47] – The critical process of defining brand personality before visuals
• [26:04] – “Punching above your weight” and startup/enterprise perception
• [32:54] – Employee recognition & “soft ROI” of out-of-home campaigns
• [36:20] – Measuring brand campaign impact qualitatively with Gong’s own tool
• [42:30] – How to build a courageous marketing team and culture
• [46:08] – Gong Labs as a content “fund returner”; actionable, data-driven insights
• [50:27] – The future: why AI makes courageous marketing even more vital

Final Thoughts & Recommendations

To Stand Out in B2B:

• Define your brand’s personality, then let everything flow from that.
• Be courageous—take calculated risks; safe is saturated.
• Amplify small but bold plays for outsized perception and employee pride.
• Build teams that feel psychological safety to experiment.
• Leverage your product for one-of-a-kind, data-led content.
• Budget proactively for experiments—protect boldness from short-term scrutiny.
• Use AI to automate the mundane, but keep courageous creative thinking at your brand’s core.

Learn More

• Courageous Marketing (Book): Available on Amazon and other retailers.
• Connect with Udi on LinkedIn: The only “Udi Ledergor.”
• Exit Five B2B Marketing Community: exitfive.com
• Podcast Guest Recommendations (from Udi’s Book):
  Carrie Lou Dietrich (Atlassian), Tricia Gelman (Box), Michelle Taite (Mailchimp), Andrew Davis (Paddle), Russell Banzon (Cresta), plus endorsements from Daniel Pink, Robert Cialdini, Nir Eyal, Neil Patel, and more.

This summary skips advertisements and non-content sections to focus on key learnings and actionable advice shared in the episode.