Best practices are boring practices. By the time everyone is doing something, you are already losing.
"Courageous marketing is about leaving behind the so-called best practices, which in reality are boring practices because by the time anything becomes the best practice, everyone's doing it," Udi Ledergor says. "So all you're going to get are mediocre average results."
The alternative is a sharp, new, unique point of view applied to everything, from content marketing to brand awareness to event experiences to demand gen.
Jeffrey Moore wrote about it in Crossing the Chasm: the gap between early adopters and the early majority is where most companies die. Early adopters will try any new tech. The early majority wants proof. Reference customers. They want to know you will still be around in two years.
"How will you go about selling to these large enterprises when they don't want to buy from startups?" Ledergor asks. "They don't think the product is built out and stable enough. You don't even have enough reference customers."
His answer is a six-step formula that makes any company appear two years ahead of where it really is. He has used it for Times Square billboards, a Super Bowl commercial, and cars wrapped in branding at major conferences, all on far smaller budgets than people assume.
Step 1: Pick a medium tied to large advertisers.
Times Square. The Wall Street Journal. The Super Bowl.
Step 2: Find an affordable way in.
Digital billboards in Times Square cost $500 for one day if you buy online. The Wall Street Journal's West Coast edition costs 20% of the national rate. Super Bowl spots in three strategic regions cost about 5% of a national buy.
Step 3: Get creative.
Ledergor showed a VP of Sales sitting alone in an empty office during COVID for his Super Bowl spot. He used Times Square billboards to celebrate outstanding employees, making their teammates want to be on that billboard the following year.
Step 4: Hire a photographer.
"Put someone in Times Square. If you know that your billboard is going to be up for one hour, make sure they're sitting there 15 minutes before." Get great photos with all the hustle and bustle of the city and you have memorialized an iconic moment.
Step 5: Share to your real audience.
Gong has over 300,000 followers on LinkedIn. "I don't care about the random tourists on their way to see Phantom of the Opera. I care about the people following Gong on LinkedIn." They are the ones who need to see it.
Step 6: Mobilize your team.
Gong has 1,600 employees. Assume 500 followers each. If half share the post, that is hundreds of thousands or even millions of impressions. Free.
"That's where Apple promotes their new iPhone. That's where Netflix promote their new series," Ledergor says. "The medium is the message."
Ledergor hears the same question every time he teaches at Pavilion CMO school or works with VCs and accelerators: how do you get approval for any of this? He gives four answers.
Preemptive budgeting.
Every budget Ledergor submitted included a line for "marketing experiments," set at 10% of his program's budget. A team member named Russell stopped him from labeling it "Udi's crazy ideas" before it went to the CFO. The pitch rests on two arguments. Every channel you rely on will stop working at some point. You just do not know when. And there will be opportunities next year that you cannot see during budget season. You need room for both.
Run pilots.
"I look for a way to do it small enough that I can go under the radar. If I spend a few thousand bucks and it doesn't work out, there's probably a good learning in that." Once something works, show the numbers and ask for more. Go from a quiet $5,000 pilot to a $20,000 task with results to back it up.
Avoid death by committee.
Ledergor cites British writer G.K. Chesterton: "I searched all the parks in all the cities and I found no monuments or committees." Committees push every decision toward a mediocre middle. Everyone gets a little of their way. The result is a mess that excites no one.
In early stages, keep the room small. In later stages when committees are unavoidable, use a framework like RAPID to set roles up front. Recommender, approver, performer, informer, decision maker. "I'm the recommender, my CEO is the decision maker, all of you are informers, which means I would love to hear your opinion. Don't expect it to necessarily show up in the final product."
Know when to leave.
"Sometimes you're a great marketer not in a great environment. If you've tried everything and you're still coming up with blocks after blocks, you might be in the wrong environment." Ledergor talks in the book about how to vet companies before you join, including how to assess product market fit, which he calls the most underrated factor in marketing success.
"Life is too short to work with jerks or people who don't give freedom to your creative courage."
Attribution obsession can stop you from doing the right thing for the business. If you hold back on a campaign you believe in because you know measuring it will be hard, you are letting the dashboard drive strategy.
Gong CEO Amit Bendov frames it directly: if you run a campaign and the phone is ringing off the hook, you do not need a dashboard to tell you it worked. If you get crickets, you know that too. The problem is when the truth falls somewhere in the middle.
Ledergor's advice is to run the experiment anyway, and to ask for that freedom when you are already hitting your targets. When the numbers are good and you have budget left, asking for $20,000 to try something you cannot fully measure is a much easier conversation than asking for a Hail Mary when you are already behind.
That said, Ledergor found ways to measure where others gave up. After one Super Bowl commercial, he went into Gong and found 452 sales conversations that mentioned it. He tracked 40 buyers who came in quoting the episode of the Michael Lewis podcast he had sponsored. Exact numbers. Not guesses.
"I've never seen a company succeed when sales and marketing operated in silos," Ledergor says. "I just don't think it can be done."
Ledergor dedicated the entire last chapter of his book to this topic, practically co-writing it with Ryan Longfield, his longtime CRO at Gong.
At Gong, marketing regularly uses the platform to listen to sales calls. AI tools surface trends before anyone even hits play on a recording: top pains, competitive mentions, how buyers describe the product in their own words.
"Imagine knowing exactly how your customers describe their pain so you can mirror that on your website and in your ads. Imagine understanding how the market sees your competitive differentiation."
Ideas can come from anywhere on the team. An SDR named Nicolette heard Gong was planning its first customer conference and pitched calling it "Celebrate," a nod to selling and a celebration of salespeople. That name stuck. Six years later it is still the name.
Another SDR, Sarah, started posting on LinkedIn about her path from SDR to AE. Marketing noticed. They brought in a videographer, posted the series on Gong's official channels, and gave her a much bigger audience. It ran for months. Sarah got her promotion and moved on.
Then there is the content side. The first two people who had the biggest impact on Gong's content marketing, Chris Orlaub and Devin Reed, had never held a marketing job. Both had been salespeople. Gong sells to salespeople. Having writers who had lived that life made all the difference.
"I can teach anyone how to be a decent enough writer," Ledergor says. "But I can't teach anyone an experience that I haven't been through."
When a former salesperson writes a post that opens with "It was the last day of the quarter. I was 150K short on my quota. I didn't know if I was going to make it," salespeople want to keep reading. That is something you cannot fake.
Ledergor has seen both, and the bad use has a direct predecessor.
Fifteen years ago, CMOs boasted about outsourcing blog posts to writers for $50 each. Writers who had never worked in the industry, did not know the culture, and produced fluff built from a few Googled facts loosely tied together.
"Back to present day, I'm seeing marketers abuse AI to create content because they feel they have a quota to fill. I need a blog post every week. AI can do that, can do 10 of them a day if you want, but who's going to read that? Anything you're asking AI to write for you is a regurgitation of everything that people have already written."
Good AI use is repurposing. Take one piece of content and let AI slice it into social posts, a long-form SEO version, and variations for different platforms. Fast, and it works.
For original ideas, Ledergor points to a method from CMO Kyle Lacy. Ask ChatGPT for 10 campaign ideas. Then put all 10 aside and never look at them again.
"Now we have our creative juices flowing. We can actually create something interesting and original because these 10 ideas that ChatGPT gave us are the most worn out, overdone ideas in the world because that's how ChatGPT was designed." It read all the state of the art and regurgitated it. Now go make something else.
Paxton Gray talked about how he was a Gong customer before he ever spoke with Ledergor. He heard Gong sponsor podcasts in the business and leadership space over and over for months during his evening walks.
"I probably listened to maybe 9 or 10 commercials before finally I thought, I'm going to check it out."
That is not luck. Show up where your buyers are. Stay consistent. Make it impossible to ignore.
"Get out there, be bold, put the best practices behind you, do something creative," Ledergor says. "You either end up with a great story and a great learning, or you actually drive the business outcomes that you're after."
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/.
00:19 - What is courageous marketing
01:29 - Punching above your weight concept
06:57 - The six-step formula breakdown
30:29 - Sales and marketing alignment
31:08 - AI use and abuse in marketing
34:37 - Using AI for ideation properly
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.
