How could I not love a marketing book that says — on page one — that “great marketing makes sales easier”? That’s long been a mantra of mine, the North Star that drove my marketing career, and it served me well for many decades.
Today, I’ll do a review of Courageous Marketing by Udi Ledergor, Chief Evangelist and former CMO for over 6 years at Gong. Let me preface this by saying I have always been a huge fan of Gong. From the first second I saw Gong, I thought, “this connects the C-suite to ground reality” and used the product at the companies I ran and recommended it to the other startups I worked with.
I always told CEOs this: “Buy Gong, get together as an e-staff, and listen to 3-5 sales calls. When you’re done listening, crawl back out from under the table, and then you can decide what you want to do about it.” That’s what happens when you get connected to ground truth. That’s how “cringe” your reality often is compared to your management team’s expectations.
Everyone had onboarding programs, everyone had quarterly update training, everyone had certification, but nobody knew what was actually being said on sales calls. Gong eliminated that problem. I was fascinated to see more emergent use cases later arise like forecasting based on activity. I was unsurprised to see the space eventually consolidate around a broader sales platform with Zoominfo buying Chorus, Clari acquiring Wingman, Gong acquiring RightBound, and Outreach acquiring Canopy, among other examples.
Throughout its history I always felt that Gong was one of a very few enterprise software companies that was not only a clear leader in its market, but also had a distinct brand and personality. Others might include Salesforce and Splunk.
In Courageous Marketing, Udi tells you where that personality came from and how they fought to define and maintain it. The book is organized as a series of twelve short chapters, each containing a series of related lessons.
- A Super Bowl Commercial describes the process for getting board approval, executing, and then socially promoting a 2021 Super Bowl commercial they aired regionally. The commercial was quite good in my opinion — unlikely to win any awards for creativity from advertising groups — but clear, simple, and benefit-oriented messaging told in an interesting way. It was a gutsy move, and it worked, but it led to a second, not-good commercial in 2022 that Udi later discusses. Don’t let starting with a chapter on Super Bowl ads turn you off (as it initially did me). There’s plenty of great, less rarefied stuff coming.
- The Riskiest Strategy of All, which according to Udi, is playing it safe. He describes how Gong didn’t play it safe with either its visual identity or with its messaging. He describes the focus and consensus problems that often result in mediocre, least-common-denominator marketing and punches it home with one of my favorite quotes: “I’ve searched all the parks in all the cities and found no statues of committees” from GK Chesterton. One great way to not play it safe is to speak your buyer’s language. A lot of the corporate veiling drops off when you do that. And you’ll sound different.
- Punch Above Your Weight. I’ve often heard it said that marketing’s job is to “make us look bigger than we are” or, in my case, additionally to “make us not look French” (chez Business Objects). I think every CMO needs to make their company look bigger (and, if applicable, less French) as well as somewhat further along with its vision. As Larry Ellison once said, “sometimes I get my verb tenses mixed up,” which is fine on the about-us page, if not the product one. Udi describes a technique straight out of pre-stoic Ryan Holiday where you “advertise offline, amplify online,” for example, by buying a half-hour’s worth of the NASDAQ billboard in Times Square and then amplifying it via social media. He then importantly shares some thoughts on measuring brand investments, including using Gong to do so (e.g., counting references to a podcast appearance in sales calls).
- You Can’t Own Brand, which echoes one of my favorite David Packard quotes (“marketing is too important to be left to the marketing department”) and one of my favorite Henry Ford quotes (“quality is doing it right when no one is looking”) – or its marketing equivalent from Jeff Bezos, “your brand is what people say about you when you’re not in the room.” To the extent branding is determined not just by what you say, but by what you do, he outline Gong’s operating principles – not corporate values, mind you – but actionable principles people could follow in their day-to-day work (e.g., create raving fans). In short, as Udi says, “the takeaway is clear: marketing can’t succeed if brand-building is a disjointed exercise, separate from the rest of the company.” He ends the chapter with advice straight out of Seth Godin: don’t be boring.
- Should You Build a Category? This chapter alone is worth the price of the book because Udi provides reasoned pushback on the Play Bigger argument that to win in Silicon Valley you must to create and dominate a category — which itself is arguably a reskinned version of Geoffrey Moore who said to create a tornado and then emerge from it as the gorilla. (Moore mixed metaphors, but we love him nevertheless.) In addition to the category creation challenges Udi mentions, my problem with this is that as Silicon Valley matures, more and more categories have already been created — so life is not as simple as homesteading an unoccupied piece of the market as it was in the 1990s to 2000s. Today, I tell people: if you want to create a category, go sell some software. (Which means we need to talk about how you’re going to do that, which quickly takes us back to marketing strategy.) Udi’s viewpoint is not miles away. Though he does observe that in certain situations, classical category creation remains relevant, and Gong’s situation was one of them with Revenue Intelligence. He outlines who they hired to do this, how long it took (3 years), the approach they used (market the category, not the product), and how they measured it.
- Would You Pay For Your Content? This is a delightful essay on content marketing. It introduces the 95/5 rule of B2B marketing (95% of buyers are not in-market) and ergo the need to find those few in market while nurturing the rest, and producing content that works for both audiences to avoid “pitch slapping” the vast majority who are not currently in-market. He provides a nice differentiation between product marketing and content marketing. He wraps up with a case study on Gong Labs, which I always thought of as a great, data-driven content factory, much in the same way I think of Peter Walker’s content today at Carta. The difference is that Gong sells to sales and can express a totally different personality in presentation. One early headline was, “Secret #1 – Shut The F*ck Up” in a piece that analyzed talk/listen ratios on successful sales calls.
- Creating Events Magic is a topic about which I need no convincing. I am a huge fan of well-executed events, both large and small. Especially now, in the post-Covid but still somewhat WFH-heavy world, people like to get out and talk to each other. This chapter is an excerpt/rewrite of a book Udi published in 2015, The 50 Secrets of Trade Show Success. It’s quite tactical, but it’s good. Tradeshows are all about tactics.
- When Things Go Wrong discusses how to handle things when some of your bold experiments backfire, like the example he presents where – and this is somewhat unbelievable – they tried to leverage the murder of George Floyd by making donations to the NAACP in return for G2 reviews. While there may be no statues of committees in parks, no committee in a zillion years would have approved this campaign. He discusses the fast, direct approach he took to dig out from this mistake. Then he discusses the second, unsuccessful Super Bowl commercial. There are a few good lessons here, but IMHO he misses the biggest one: make sure your CEO understands that you’re taking risks and once in a while they’re going to blow up on you. Put differently: if you want fewer mistakes, I can take smaller risks, but that might also reduce sales. Get some buy-in on your chosen risk profile before the shit hits the fan. You might need it.
- Chart Your Own Path is a chapter on career that encourages you to carve out roles that fit your strengths, work at startups that have already achieved product-market fit (PMF), and to pick the right company at which to work. The right company not only has established PMF, but has a CEO whose vision for marketing aligns with yours and your styles work well together. We all know a perfectly good marketer who suffered because they joined a company that didn’t pass one or more of these tests.
- Lay The Foundation For Greatness emphasizes the importance of having a high-level marketing strategy that is aligned with company goals so people can understand not only the details of your plan but the underlying logic behind it. Understanding both is key to driving commitment. He also emphasizes an idea that I heard almost verbatim from one of my bosses when I was a CMO: wear two hats. Or, as it was put to me: “you have two jobs – one is to run the marketing department and the other is to help me run the company.” The natural consequence is that you must build a strong team beneath you, so that you have time for your second job. Too many CMOs fail because they never get beyond the day job, and that is usually a result of a weak team or insufficient resources. If your CEO tells you, “you have two jobs,” then make sure they’ve given you the resources to do them both. One of my rare disagreements with Udi is at the end of this chapter where he advocates for executives taking positions on social and global issues. I think that’s a slippery slope and a mistake and, as Udi foretells, I’ll be someone who respectfully disagrees with him on that viewpoint. My quip on the general issue of enterprise software companies taking official positions on social and global issues is: “Sir, this is an Arby’s.”
- Building a Courageous Team shares Udi’s views on teamwork, including his take on when to hire for potential over experience, sequencing how you build a marketing team as a company scales, and the culture that drives great teamwork. He shares three of their operating principles: foster of a culture of healthy risk-taking (a central thesis of the book), stay involved without micromanaging (easier said than done), and keep it simple. I’ll take his third principle one step further: I think it’s marketing’s job to impose simplicity on a complex and chaotic world.
- You’re Half of a Two-Headed Dragon recognizes that reality that sales and marketing are partners in revenue generation. My favorite metaphors are “we’re running a three-legged race” and, more colorfully, “the CRO and CMO are lashed together as a human battering ram.” If Udi likes dragons, so be it. He repeats his belief that marketing exists to make sales easier (amen) and shares five principles of sales and marketing alignment.
The book ends, fittingly, with a list of tips from CMOs on how to do more courageous marketing.
While you shouldn’t judge a marketing book by its cover, you can judge it by its marketing. And Udi has done an impressive job here. The back cover quotes come from a high-firepower list including Daniel Pink, Robert Cialdini, Nir Eyal, Neil Patel, Carilu Deitrich, and Kyle Lacy. The forward is written by Sam Jacobs of Pavilion. The interior quotes include Trisha Gellman CMO at Box, Dave Gerhardt from CMO at Drift and founder of Exit 5, Dave Kellogg (I served as an advance reviewer and provided a quote), Jon Miller cofounder of Marketo and Engagio, Andrew Davies CMO of Paddle, and Anthony Kennada former Gainsight CMO and founder of Goldenhour.
The book was published in April to some great coverage. I’ve recently noticed Udi doing some double-dip marketing on social media. Those posts provided me with enough energy to complete my long-overdue review.
Courageous Marketing is a quick and uplifting read. I’d knock it off on an upcoming airplane trip to get your marketing juices flowing. It could also be the perfect stocking stuffer for the marketer in your life.



