From Zero to Hundreds of Millions: Lessons in Courageous Marketing

The Gong CMO's Step-By-Step Guide to Standing Out

In Udi Ledergor's new book, Courageous Marketing, the former CMO of Gong shares how he helped transform a startup with just 12 customers into a revenue intelligence powerhouse worth billions. As someone who advises tech leaders regularly, I found Ledergor's practical insights refreshing in their boldness and honesty. The book goes on sale today - buy it here.

The book offers a masterclass in B2B marketing that breaks free from the "sea of sameness" plaguing most tech companies today. Rather than settling for stock photos of handshakes and bland corporate language, Ledergor demonstrates how taking calculated risks can yield extraordinary results. His book launch video itself underscores his philosophy that being courageous and unexpected can make you stand out from the crowd:

The Risk of Playing It Safe

Perhaps the most counterintuitive lesson in the book is that the safest strategy is often the riskiest of all. When every competitor is playing by the same rulebook, blending in becomes a death sentence. Ledergor argues that standing out requires courage—the willingness to try approaches that might initially seem outlandish.

Take Gong's visual identity, for example. While competitors used subdued, "safe" color palettes, Gong went wild with bright colors and even adopted a bulldog mascot that appeared everywhere, from their website to their chatbot. When a puzzled customer asked, "Why is there a bulldog on my log-in screen?!" they knew they'd created something memorable.

Udi shares in the book that he was an entertainer growing up - literally a magician who would levitate people and cut them in half. Plus he was an accomplished musician and puppeteer(!) His underlying philosophy is that ”Marketing is really just putting on a show. It’s the business form of performing arts.” You can see this play out in his creative, courageous decisions.

The Super Bowl Gambit

The most fascinating story in the book details how Gong, then a relatively small startup, managed to run a Super Bowl commercial—a marketing tactic typically reserved for consumer giants with massive budgets.

Ledergor pitched the idea to his CEO over drinks, explaining a crucial insight: "Turns out we can buy regional media where our target audience is," he told his CEO, "at a fraction of the cost of the national spot." Rather than paying $5+ million for a national Super Bowl ad that most companies expected, Gong could strategically target just the markets where their buyers lived.

While skeptical board members eventually approved the plan, Ledergor's CEO forwarded their email with a simple note: "Basically, your neck is on the line. Good luck."

Facing COVID restrictions and a modest budget, Ledergor worked with a small video production agency to create a commercial featuring a sales VP who appeared tiny in a giant, empty office—a quirky reflection of pandemic-era workplace culture.

Instead of following conventional wisdom to wait until Monday to promote the commercial, Ledergor shared it on LinkedIn on Super Bowl Sunday morning. The results were astonishing: over a thousand engagements, hundreds of comments and shares, and a flood of social media buzz when employees and industry influencers amplified it.

The regional buying strategy proved brilliant—using Gong's own revenue intelligence software, Ledergor tracked hundreds of customer mentions of their commercial, confirming their targeted approach had worked. Most impressively, the Super Bowl week marked an all-time record for sales pipeline creation at Gong, demonstrating that courageous marketing can deliver tangible business results.

Looking Bigger Than You Are

Ledergor shares a simple framework for startups to appear more established than they really are:

1. Pick an offline medium typically associated with larger companies

2. Buy a small, affordable version of it

3. Get creative with how you use it

4. Photograph it to make it appear bigger

5. Share extensively on social media

6. Activate employees and customers to extend reach

This "punch above your weight" strategy helped Gong create the perception of being a much larger company, which attracted customers who might otherwise avoid startups.

The book offers several compelling examples of this approach in action:

Times Square Billboard: While most assumed Gong spent a fortune on Times Square advertising, they actually purchased just 15 seconds of time on a small billboard for a few hundred dollars. They sent a photographer to capture the moment with the hustle and bustle of Times Square in the background, then amplified these images on social media to a much more relevant audience than the billboard itself could reach.

The Wall Street Journal Ad: Instead of paying for the pricey national edition, Gong bought ad space in the more affordable West Coast edition. They photographed the ad once published and shared it on social media, achieving the same perceived impact as the national edition at a fraction of the cost.

Virtual Billboards: During COVID, when few people were walking the streets, Gong commissioned a graphic artist to create virtual billboards and Photoshopped them into Times Square. While not hiding that these were digital creations, many followers assumed they were real and engaged enthusiastically, especially when Gong featured employees of the year on them.

Warriors Game Overlay: In another clever move, Gong purchased a virtual overlay of their logo on the Warriors' basketball court during a game. By luck, Steph Curry broke his three-point shots record while hovering over the Gong logo. This iconic moment was widely shared by the Warriors, NBC, and Gong fans, exponentially amplifying its reach.

As the book demonstrates, these techniques allowed Gong to dominate small geographic regions strategically, creating the perception of a much larger company. When asked at a company event how many employees Gong had, Ledergor was asked, "About a thousand?" — when they actually had fewer than 200 at the time.

More "Courageous Marketing"

While this article only scratches the surface, "Courageous Marketing" offers actionable insights on numerous challenges facing B2B marketers. Critical topics Ledergor addresses include:

• Overcoming "Death by Committee" – How to avoid the innovation-killing practice of seeking universal approval that leads to bland, ineffective marketing

• The 95-5 Rule of Content Marketing – Why 95% of your potential customers aren't ready to buy right now, and how to create content that builds memory links that activate when they are

• Category Creation – A detailed case study of how Gong created the "Revenue Intelligence" category, with practical steps for defining a new market space

• Creating Content Worth Paying For – How to develop marketing content so valuable that customers would actually pay for it (including real examples of customers who asked to)

• Event Marketing Excellence – Strategies for maximizing ROI on trade shows and conferences, from booth configurations to staffing approaches and post-show follow-up (this is a detailed gold mine)

• Learning from Failures – Honest discussions of marketing campaigns that flopped, including their second Super Bowl commercial that cost three times more but achieved far less

• Building a Marketing Team – Practical advice on early hires, fostering a culture of healthy risk-taking, and attracting top talent

• Sales and Marketing Alignment – Five principles for creating what Ledergor calls a "two-headed dragon" where both teams work in perfect synchronization

• Taking a Stand on Issues – How and when marketing leaders should use their voice on social and global issues and the benefits of doing so authentically

Besides detailing his own journey and techniques, Udi also included perspectives and advice from a whole host of fantastic marketers I respect, including Trica Gellman, Anthony Kennada, Dave Gerhart, Michelle Taite, and Andrew Davies, and, in quite an honor, me too : ) But what made this book really rich for me was the detailed, practical, behind the scenes lessons from really BUILDING a company from scratch. Not too many people have gone from so little to so much, and even fewer have shared their stories like this. Udi is entertaining and inspirational.

This book is a refreshing alternative to conventional marketing playbooks and company constraints. Udi proves that with the right approach, even a small company can create an outsized impact. Buy the book now here.

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Carilu Dietrich is a former CMO, most notably the head of marketing that took Atlassian public. She currently advises CEOs and CMOs of high-growth tech companies. Carilu helps leaders operationalize the chaos of scale, see around corners, and improve marketing and company performance.

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