Most B2B marketers are stuck playing it safe, following “best practices” that guarantee mediocre results. Udi Ledergor, former CMO of Gong and author of Courageous Marketing, has spent his career doing the opposite—running Super Bowl ads for 5% of the expected cost, getting Times Square billboards for $500, and building a marketing machine that made Gong impossible to ignore.

In this conversation, Udi breaks down the exact six-step formula he’s used repeatedly to make companies appear years ahead of where they actually are—and why this matters more than ever for early-stage companies trying to cross the chasm to enterprise buyers.

Key takeaways for B2B marketers:

• The six-step formula for punching above your weight: How to leverage iconic advertising mediums (Times Square, Wall Street Journal, Super Bowl) for a fraction of what you’d expect—then amplify that investment through your owned channels and employee networks
• Getting experimental budgets approved: Why every marketing budget should have a 10% line item for “marketing experiments” and the two arguments that get it past skeptical CFOs every time
• Attribution without obsession: How Udi used Gong’s own platform to track that 452 sales conversations mentioned their Super Bowl ad—and why you shouldn’t let attribution fears stop bold campaigns
• Sales as your secret creative weapon: Why Gong’s best content marketers were former salespeople, not traditional marketers, and how to tap into your sales team’s market knowledge
• AI for creativity (the right way): Kyle Lacy’s framework for using ChatGPT in brainstorming—get 10 ideas, table them all, then create something original

Udi also addresses when it’s time to move on from a company that won’t let you be courageous, how to vet product-market fit before joining a startup, and why the “medium is the message” principle is more powerful than ever in an era of digital dashboards.

If you’re tired of blending in with every other B2B company and want permission (plus a playbook) to do something bold, this episode is your rallying cry.

Resources: 

Get your copy of Courageous Marketing: The B2B Marketer’s Playbook for Career Success here: https://www.amazon.com/dp/B0F22HWR3C 

See what Gong can do for your business: https://www.gong.io/ 

Follow Udi on LinkedIn: https://www.linkedin.com/in/udiledergor/ 

Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ 

Looking for an agency that’ll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. 

About Udi Ledergor: 

Udi Ledergor, a five-time B2B marketing leader, served as CMO during Gong’s rise from new SaaS startup to industry dominance. By building a playful, human-centric brand with a lighthearted tone, he captured buyers’ attention and dollars and turned them into raving fans. He later led the creation of the revenue intelligence category, which helped Gong go from zero to hundreds of millions in revenue, earning major industry awards and achieving a multi-billion-dollar valuation. Over his 20-year career, Udi has led marketing teams at successful companies, advised startups, served as a board member and angel investor, and mentored hundreds of marketers. His work reveals how courage and creativity can build iconic brands, connect with audiences, and drive measurable results.

Timestamps: 

01:09 – What is courageous marketing

02:04 – Punching above your weight concept

06:57 – The six-step formula breakdown

24:59 – Sales and marketing alignment

32:09 – AI use and abuse in marketing

35:27 – Using AI for ideation properly