Category Archives: Strategy

A Review of Courageous Marketing by Udi Ledergor

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.

The Era of Haves and Have-Nots

Below I’m cross-posting an article I wrote for the launch of Topline Media, the media spin-out from Pavilion, a popular community for go-to-market (GTM) leaders. This article was originally published by Topline on 10/9/25.

Since this was written for the launch of a new publication, I made it somewhat more sensationalist than usual. It’s also shorter and tighter, without the usual deep-drives and asides.

The reception was not without controversy, in part because I touched the third rail by mentioning 996. Some hastily took that to mean, “some VC is telling portfolio companies to grind 996.” That I’m not a VC and never told everyone to blindly grind 996 seemed beside the point.

What I said was: if you’re in a winner-take-all market, then you need to win. Grinding 996 might be a part of that. But the point isn’t to work hard, it’s to win. You can grind yourself to death at a strategically doomed company and it won’t change much. (I’ve tried that. AMA.)

Here’s the article. Thanks to Sam Jacobs and Asad Zaman for inviting me to write it:

AI has created an era of haves and have-nots.  AI-native companies with spectacular growth rates are grabbing all the attention, talent and money.  Is this insanity?  How long will it last?  If you’re not among the ranks of the AI-native high flyers, how do you avoid becoming seen as a zombie, a living-dead SaaS company with uninteresting growth, little profit, and no future?  

First, it’s important to understand the external environment.  While the world may seem insane, it’s not.  We are at the start of a major disruptive cycle on the order of client/server computing or the Internet.  Such cycles come maybe every 20 years in my experience, just long enough for us to have forgotten what they feel like.  

These technology disruptions create opportunities to build enormously valuable companies that will lead their markets for a generation.  This is the system at work.  It’s chaotic.  It’s inefficient.  It feels crazy when you’re in it.  But always remember that from the wreckage of Webvan, Pets.com, and a hundred other dot-coms, sprung Amazon, Google, and Salesforce.  Nobody said creative destruction came without casualties.  

These cycles reflect the nature of venture capital.  While fixer-upper private equity (PE) has always been about driving modest growth with ever-increasing EBITDA margins, venture capital (VC) has always been a hits business.  I remember nearly a decade ago reading the prospectus of a top-tier fund which said that the internal rate of return (IRR) of their previous fund was 36%, but that dropped to 12% with the top two investments omitted.  Most of what makes VC a great investment, worth the 10-12 year illiquidity, comes from a handful of fund-returning companies.  While consistent base hits are the PE business model, the VC model is not just about home runs, but grand slams.

Viewed in this light, today’s ARR multiples seem much less insane.  After all, if a company is going to be worth $20B at exit, it doesn’t matter much if you bought at a valuation of $50M or $80M.  This is what drives the valuation insensitivity and fear-of-missing-out (FOMO) that we see today in AI.  Moreover, if you remember that in greenfield platform markets, first place ends up worth 10-100x second place, and second 10-100x third, you should be willing to pay almost anything to get into the leader.  And if you’re currently in second place, you should be willing to spend almost anything to get into first.  Second prize really is a set of steak knives.

While some will question the durability of high-growth AI revenue, to many investors it’s surprisingly unimportant.  Yes, a lot of the $100M in revenues (that a company hit in 18 months) may not recur, but 70% of something is worth a lot more than 100% of nothing.  Thus, we are seeing a surprising lack of interest in traditional SaaS metrics and the very notion of ARR — particularly the recurring part — is starting to lose meaning.  Increasingly, companies are just talking about revenue or product revenue because today’s pricing models (e.g., consumption, outcomes) no longer align to subscriptions and traditional SaaS metrics.  

While we can’t help wondering how long this will last, that’s the wrong question. It will last until it doesn’t.  Shorting bubbles is a dangerous business because the market can stay irrational longer than you can stay liquid.  Eventually, some trigger will start an unwind cycle. And once again, we will learn that this time wasn’t different from all the times before.

If you’re an AI-native growth company, the strategy is simple:  win.  Take no prisoners.  Grind 996.  Grow faster than your competitors, blunt all attempts to overtake you.  In the words of Larry Ellison, it’s not enough that you win, all others must lose.  Hire people who are so aggressive they make you uncomfortable.  Think:  “you want me on the wall, you need me on that wall.”

But what if you’re not?  Per Jason Lemkin et al., you probably can’t raise new money.  Even T2D3 (triple, triple, double, double, double) — a growth trajectory that takes you from $0 to $100M in seven to nine years — is no longer interesting to 80% of VCs.  Instead of T2D3, we hear of Q2T3 (quadruple, quadruple, triple, triple, triple).  We now measure time to $100M in ARR in months, not years.  And, by the way, do it with a tiny team, driving ARR/head of $1M+.

That the bar has been raised so high is a mixed blessing because now there’s no kidding yourself.  There’s no pitching a cloud story while still selling on-premises.  The bluff factor has been eliminated.  If you want to raise money at an AI valuation, then you don’t just need an AI story, you need an AI growth rate to match it.  Clear and simple, but far from easy.

If 80% of VCs aren’t interested in talking to you, how might you win over the other 20%?

Hunkering down is not good enough.  Particularly if hunker means something like 10% growth and 5% EBITDA at $30M in ARR.  Financially, that business might be worth 10-20x FCF, so $15M to $30M.  That’s not bad if you’re bootstrapped and you’re a founder who owns 100% of the company.  But, even then, that works only if there is confidence that the $1.5M in annual EBITDA will continue.  That is, that you won’t be disrupted by AI natives who vibe code your replacement app over the weekend.  However, if the same business raised $50M in VC then it’s effectively worthless, because the entire business is worth less than preference stack.

So how do you create value?  One word:  growth.  Growth is what takes you from an EBITDA-based multiple to a revenue-based multiple.  Mathematically, a point of growth is worth about 2.3x a point of profit.  One way or another you have to figure out growth. 

But how?

  1. Make growth at positive FCF the top financial goal.  Note that this is not a strategy, but a constraint.
  2. Build an AI story. Do an inside round, raise debt, or even cut traditional R&D if you need to, but you have to find money to build an AI product and story.  If you get it right, it will not only enable current sales but increase your value at exit.
  3. Be relentless in sales model optimization.  You are fighting for your corporate life.  This isn’t about arguing with the board about how much to invest in growth.  You are highly constrained, but let those constraints drive creativity.  Do market research.  Do win/loss analysis.  Get good at listening. Figure out what you can do to improve sales productivity.  Often, that will be doubling down on a key segment.  Or stopping in an unproductive segment.  Or changing key assumptions in your sales model (e.g., SC to AE ratio, AE hiring/cost profile) that might have been heretical to consider in the past.
  4. Consolidate the space.  Investors who have “no money” for operational experiments often do have money for new strategies.  If you’re competing with the usual suspects in every deal and everyone is struggling, then consolidate the space.  It should increase both win rates and prices.  
  5. Fresh eyes.  You might think you’ve tried everything already over the past few years.  But have you?  And if you tried something and it didn’t work, was that because it was a bad idea or because you didn’t execute it well?  Beware false knowledge that blinds you to solutions.  Or bring in fresh eyes to challenge your assumptions.  Yes, it’s not going to be easy, and yes you’ve tried a lot already, but you need to look at things with fresh eyes to find fresh solutions.

In a world of haves and have-nots, you want to be a have. And the key to doing that, no matter how many times you’ve tried before, is to figure out growth.

Slides from Balderton Webinar on Aligning Product and GTM Using Customer Value Metrics

Today Dan Teodosiu, Thor Mitchell, and I hosted a Balderton webinar entitled Aligning Product and Go-To-Market (GTM) Using Customer Value Metrics. We are all executives in residence (EIRs) at Balderton — Dan covers technology, Thor covers product, and I cover go-to-market — and, in a display of cross-functional walking-the-talk, we came together to present this session on alignment.

The session was based on an article Dan and I wrote, by the same title, which was published on the Balderton site last month and about which I wrote here. The purpose of this post is to share the slides from that webinar which are available here and embedded below.

Thank you to everyone who attended the session and who asked questions in advance or in the chat. I’m sorry that we didn’t have the time to answer each question, but if you drop one into the comments below, I’ll do my best to answer it here and/or ask Dan or Thor to weigh in as well. I’m not aware if Balderton is going to make a video of the session available, but if they do I’ll revise this post and put a link here.

Aligning Product and Go-To-Market with Metrics

My fellow Balderton Capital EIR Dan Teodosiu and I recently published an article on aligning product and go-to-market teams using metrics, specifically customer-value metrics. In this post, I’ll talk a bit about the article and how we came to write it, with the hope that I’ll pique your interest in reading it.

First, a bit on the authors. The definition of EIR (here meaning executive-in-residence) varies widely — as does the job itself. At Balderton, it means that we are on-staff resources available to help portfolio companies, on an opt-in basis, with the issues that founders and executives face in building a startup. Dan focuses on technology and engineering while I focus on sales and marketing. Dan’s founded two startups as well as having technology leadership roles at Criteo, Google, and Microsoft, and I’ve been CEO of two startups in addition to having served as CMO of three. That means we are both able to see the bigger picture in addition to our purely functional views. Not to be immodest, but I’d have trouble finding two better people to write an article on how to align product/technology and go-to-market. Heck, we even had the expected us vs. them disputes!

I write a lot about aligning sales and marketing (always remember the CRO is the #1 cause of death for the CMO), but I’ve not written before about aligning product and GTM. So this was a new, fun challenge that necessarily led to strategy, organizational behavior, and leadership. Yes, often, the CEO is the cause of the problem. I can’t tell you the number of times I’ve said: “You want to know whose fault this is? Grab a mirror!” But knowing that doesn’t necessarily help the particpants in a mess unless they know how to get out of it. Usually that starts by asking one simple question: why would anyone want to buy this again?

Does any of this sound familiar?


It’s a 2,750-word paper, which should take around 10 minutes to read, and I’d encourage everyone to check it out. We’ve got some nice, juicy historical examples in there where good companies, even great companies, lost the plot, forgot about customer value and wasted tons of resources as a result. Spare yourselves that pain. Or, if you’re in the thick of it already, step up and start asking the one big question: why would anyone want to buy this again?

Change Management and Selling Hope Along The Way

Let’s say you’re a CEO leading your startup’s migration from mid-market to enterprise. To do that, you’ve hopefully already done the following:

  • Analyzed existing success in enterprise accounts. (Most people don’t start purely from scratch, but instead have picked up a few “accidental” customers that they hope to replicate.)
  • Hired a team to pursue enterprise, ideally with dedicated AE, SCs, SDRs and even more ideally with a dedicated CSM and marketer. Concretely, that initial team might look like 1 sales manager, 4 AEs, 2 SCs, 3 SDRs, 1 CSM, and 1 field marketer. A focused team of dedicated resources is an infinitely better approach to opening a new market segment than making it everyone’s pastime.
  • Done market research to understand the competitors you’ll encounter and the buyers to whom you’ll be selling. You’ve then made an initial strategy for beating those competitors and built messaging that maps to those buyers and their business priorities.
  • Identified product gaps. Your product team has done a study to identify missing product features that customers in the new segment will demand. You’ve made a plan that combines workarounds and the product roadmap to sell successfully despite these gaps while you work to close them. (Beware that product gaps, often involving non-functional requirements, doom more new market migration initiatives than any other.)
  • Sold the initiative to both the board and the company as a valid and important priority. This will get you buy-in at both the board and team level, hopefully evoking real commitment to the new and difficult undertaking. As part of this, you may well have set initial end-state goals — e.g., getting 25% of new ARR from enterprise in six quarters, increasing your average sales price (ASP) by 50% relative to mid-market, and increasing product penetration per account from 1.5 to 3.0 products.

That’s awesome. You’re doing it by the book. So what did you forget to do? Particularly when getting to the initial end-state might take six quarters and another year or two beyond that to look at renewal and expansion rates?

What did you forget? To sell hope along the way.

I don’t mean selling hope in the metaphorical Charles Revson way. I mean selling hope in a literal way to the team and the board. Twelve to eighteen months is too long for people to wait for results. But if it takes 3 months to build the team, 3 months to ramp them, and sales cycles are 9-12 months, then your earliest possible results are 15-18 months from when you hit the “go” button with the board. Coincidentally, that approximates the MTBF for CMOs.

How do you sell hope along the way?

  • You lay out expectations, up front. You describe how you expect things to progress over time (e.g., enterprise team staffed up, first enterprise marketing event, hit enterprise pipeline of $3M, first closed new customer). And like any expectations, you set them carefully and remind people of them often.
  • You tell stories along the way. This is the part most people don’t forget. Hey, 125 people showed up at the enterprise event. Hey, we had a great meeting at BigCo. Hey, an analyst positioned us in an enterprise report. Hey, we hosted a great enterprise dinner in Philly. This is good, but the stories start to ring hollow pretty quickly in the absence of up-front expectations setting and downstream data.
  • You use leading indicators. Sure, we all know the end-state indicators that we want. A big chunk of total ARR. Faster growth. Bigger deals. Higher win rates. Increased GRR and NRR. Those are real indicators — and they’re important — but they’re lagging and, in cases, badly. You need to find some leading indicators to track and measure along the way. For example, in the enterprise segment: pipeline size, pipeline coverage, average size of oppties, high- and mid-funnel conversion rates, number of customers. Note that when moving up market, some metrics are going to get worse (e.g., stage progression velocity) so you may as well track and set expectations for those as well.

The main point here is to not make the rookie mistake of screaming: “Mid-market is dead! Long live enterprise!” Thus setting impossible expectations for enterprise all while undermining your mid-market efforts. Instead, you should carefully think through how the enterprise initiative is going to unfold, lay that out both qualitatively and quantitatively with leading indicators, and then report back to the company and board with progress reports, war stories, and metrics.

You’ve already convinced people that the enterprise initiative is a good idea. Now you need to make and execute a plan to keep them excited along the way.