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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode, Udi Ledergor, Chief Evangelist and former CMO at Gong, discusses his new book "Courageous Marketing" and breaks down why most B2B marketing fails by playing it safe. (18:45) Udi shares his journey from marketer #1 to CMO at Gong, where he led the creation of the revenue intelligence category and helped scale the company from zero to hundreds of millions in revenue. The conversation explores how Gong built a standout brand through bold marketing choices, creative campaigns that punched above their weight, and data-driven content strategies. (23:16) Key themes include the importance of developing a clear brand personality before visual identity, using creative "perception hacks" like strategic billboard placements, and building courageous marketing teams with psychological safety to experiment.
Udi Ledergor is the Chief Evangelist at Gong and former CMO who led the company's marketing efforts from startup to hundreds of millions in revenue. He started as marketer #1 at Gong and pioneered the revenue intelligence category while building an iconic human-centric brand around Bruno the bulldog and Gong's distinctive purple identity. (03:45) Prior to Gong, Udi spent 25 years in tech including product management roles and marketing leadership positions at five companies, including taking Panaya public before its acquisition by Infosys for hundreds of millions.
Dave Gerhardt is the host of B2B Marketing podcast and founder of Exit Five, a private community for B2B marketers. He previously led marketing at companies including Drift, where he helped build the conversational marketing category and grew the company's brand recognition significantly.
Udi emphasizes that visual branding should emerge from a deeper brand personality exercise, not random aesthetic choices. (23:00) At Gong, they identified core qualities like being "mature but playful" and "authoritative but friendly" before selecting fonts, colors, or imagery. This intentional approach ensured all brand elements - from Bruno the bulldog to their purple color scheme to their tone of voice - worked cohesively. The result was a brand that felt like "that helpful friend you can approach at a cocktail party who always has a great story." This systematic approach to brand personality development prevents the common mistake of incongruent messaging where companies might use playful visuals but produce stuffy content.
Startups can appear years ahead of their actual stage by strategically using mediums typically associated with large advertisers. (28:22) Udi's formula involves finding the smallest, cheapest version of premium advertising (like regional Wall Street Journal ads or off-peak Times Square billboards), getting creative with the content, taking professional photos/videos, and amplifying extensively across owned digital channels. For example, spending $500 on a Times Square billboard for two minutes, capturing it professionally, then sharing across LinkedIn to 300,000 followers creates massive perceived scale. The goal isn't reaching random passersby - it's showing your audience that you're a legitimate, growing company worth taking seriously.
Allocate 5-10% of annual marketing budget specifically for "marketing experiments" rather than fighting for approval on each creative idea. (33:14) Udi positioned this budget by explaining two realities to leadership: unexpected opportunities will arise throughout the year that don't exist during budget planning, and current marketing channels will eventually plateau, requiring experimentation with new approaches. This pre-approved experimental budget enabled Gong to quickly capitalize on opportunities like industry events, creative billboard campaigns, and podcast sponsorships without lengthy approval processes. The key is setting proper expectations that not everything will show clear ROI on digital dashboards, but successful experiments can become permanent budget line items.
Leverage your product's unique data capabilities to produce content that provides immediate value while subtly promoting your solution. (47:07) Gong Labs became a nine-year content success by sharing insights like "salespeople who tactfully swear increase win rates by 8%" or "opening cold calls with 'how have you been' keeps people on the line longer." This approach works because the content makes readers instantly better at their jobs using insights only available through your product. Unlike generic thought leadership, data-driven content provides exclusive value that competitors can't replicate, builds authority in your space, and demonstrates product value without direct selling.
Create an environment where team members feel safe to experiment and fail while maintaining clear goals and processes. (43:34) Udi's approach involved consistently pushing his team to "go bigger" and think in 10x rather than 10% improvements, while providing the safety net of an experiments budget and the expectation that failures would be learning opportunities, not firing offenses. He combined this psychological safety with what Adam Grant calls "process accountability" - ensuring experiments served clear business objectives rather than being random acts of marketing. This balance enabled team members like Devin Reed, Russell Vanzan, and Sheena Badani to create breakthrough campaigns and category-defining work.