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.

Your Buyer Has an “I Want” Song — Does Your Messaging?

Why your messaging needs a number written for the buyer, not for you.

Musical theater offers a surprisingly useful lesson for B2B marketers: the “I want”song. Nearly every musical features an “I want” song third or fourth in the score, after we’ve been introduced to the characters but before we understand their motivations. That’s when the protagonist steps forward and articulates what they want, often in the language of longing. It is a structural requirement: the audience cannot understand the stakes of the story unless they first understand the desire that animates its hero.

Hercules wants to find where he belongs. Hamilton wants his shot. Ariel wants to be part of another world. Mulan (like Rumi) wants to be accepted as her true self. Elder Price wants to do something incredible. The details vary, but the mechanism does not: the story cannot begin until the protagonist tells us what they want.

This turns out to be a useful metaphor for B2B marketing. Every buyer has an “I want” song: usually unspoken, often half-formed, but always present. Yet most messaging fails to reveal it. Instead, we default to talking about our own technology, our architecture, our features, our AI, our category. We sing our song. When we should be singing theirs.

I like devices that force a frame switch, and thinking about “I want” songs does exactly that. They push us out of vendor-centric thinking and into a more empathic posture: what does the buyer wish were true, not only organizationally but personally? To make the idea concrete, I went so far as to draft a sample FP&A “I want” song to the tune of Go the Distance, which worked quite well as a template. The exercise also forced me into short, simple phrasing — an unexpected but useful reminder to use plain language.

That detour was fun, but let’s return to the main argument.

The reason the “I want” structure works as a messaging framework is that its underlying components — the ache, the aspiration, and the bridge — map surprisingly well onto the way buyers perceive their own situation.

First comes the ache: the protagonist’s sense that something is missing. Ariel feels trapped; Moana feels pulled toward something beyond the reef; Hercules feels out of place. In a business context, the ache is rarely “we need AI-driven orchestration.” It is more grounded and more personal:

  • I want to stop feeling constantly behind.
  • I want the board to stop grilling me every month.
  • I want managers to believe in the plan rather than treat it as something imposed on them.
  • I want my team to get home at a reasonable hour.
  • I want to actually do analysis instead of wrestling with systems.

These are the underlying motivations that drive buyers. As I’ve said before, marketers tend to remember the business benefits but forget the personal ones –i.e., the “kiss” in the benefits stack. Writing an “I want” song forces us to reinsert the personal dimension.

Next is the aspiration — the imagined better world. Hercules imagines belonging; Mulan imagines authenticity without alienation; Elder Price imagines extraordinary accomplishment. In FP&A terms, aspirations could include:

  • A plan that people believe in and are committed to
  • A model that can be updated without triggering a cascade of breakage.
  • A planning cycle that doesn’t consume nights and weekends.
  • A finance team that is viewed as a strategic partner rather than a reporting function.

These aspirations, importantly, should be described in terms the buyer actually uses, not in vendor jargon.

Finally comes the bridge — the mechanism that makes the aspiration feel reachable. In a musical, this is the moment when the hero decides to act. In marketing, this is where the product finally enters, not as the hero but as the tool that enables the hero’s journey. If the ache is “I’m stuck in Excel hell” and the aspiration is “I want a planning process that people trust and that lets me get home for dinner,” then the bridge might be: This system will take me from the chaos I live with today to a world in which the plan is credible, the board is confident, and I’m not working every weekend.

In this framing, the buyer is the protagonist and you are the mentor, guide, or map. The best narratives work this way. The worst invert the roles.

Unfortunately, much of modern B2B messaging still sings the wrong song. “We’re an AI-enabled platform delivering real-time insights at scale” is an “I am” song. The buyer does not care who you are until they understand why it matters. A better start would acknowledge the ache, gesture toward the aspiration, and only then offer the bridge: “FP&A teams spend 30% of their week pulling data instead of analyzing the business. Our platform gives them that time back.” That’s the beginning of an “I want” song: I want to put the A back in FP&A.

Companies that successfully reframe markets often do this instinctively. Snowflake didn’t lead with “cloud data warehousing”; they led with, “I want my data to be usable.” Figma didn’t lead with “multiplayer design”; they led with, “I want design to move at product speed.” Datadog didn’t lead with “observability”; they led with, “I want to see everything before it breaks.” These are buyer “I want” statements, whether or not the companies described them that way.

Narrative, messaging, and positioning are distinct disciplines, but they share a foundational principle: the buyer is the protagonist. Your first task is to understand the buyer’s “I want,” and your second is to articulate it more clearly than they can themselves.

Try this simple test: read your homepage aloud and ask whether the buyer can hear themselves as the one singing it. If the answer is no, you are singing your song, not theirs.

You know you’re on the right track when buyers start reacting not just to your product, but to your understanding of their situation. They nod before you ever show a screenshot. They finish your sentences. They repeat your messaging back to you in their own words, often with a slight sense of relief that someone has articulated the problem. They circulate your deck internally not because it describes your offering, but because it describes their goals. They say things like, “This is exactly what we’ve been trying to do,” or — my personal favorite thing to hear — “It sounds like you’ve been in our meetings for the last three years.”

Let’s net this out: if this were a musical and your buyer was the protagonist, what “I want” song would they sing?

Figure that out and you’ll build some powerful messaging. But don’t be like me and actually try to pair those lyrics to a song — though I have to admit it is fun.

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.

How To Navigate the Pipeline Crisis

Unlike many marketers, I’m not particularly prone to hyperbole, and thus “crisis” is not a word that I use lightly.  But I think saying “pipeline crisis” is warranted today when discussing what’s happening in marketing and is a key underlying cause for the broader malaise in SaaS growth

You don’t need to look far to find signs of a problem:

  • SaaS stocks, as measured by Bessemer’s Emerging Cloud Index are down 3.4% year to date.
  • Customer acquisition efficiency is down.  Earlier this year, median CAC payback periods hit 57 months, implying a staggering almost five years to recoup the cost of acquiring a dollar of net-new ARR.
  • Pipeline coverage ratios are running below their required targets.  The top reason for missing sales targets is insufficient pipeline coverage and Cloud Ratings shows stated coverage of 3.6x vs. target coverage of 4.1x.  (I can hear the cries of CROs everywhere saying, “please, just give me more at-bats!”)
  • Articles about the web traffic crisis are ubiquitous, from Rand Fishkin’s must-read posts on zero-click marketing to CJ Gustafson swimming outside his normal lane with a post entitled Google Zero.  The web is transitioning into a series of walled gardens and what’s left over is increasingly front-run both by Google search and, of course, answer engines such as ChatGPT, Perplexity, Claude, and Gemini.
  • Earlier this year, Andrew Chen put it bluntly:  Every Marketing Channel Sucks Right Now.

Add it all up and you can summarize this rather grim picture — as the Exit Five newsletter recently did — with Nothing Works Anymore.

I see this every day in my work with dozens of SaaS companies.  Because many companies are missing bookings targets by roughly the same percentage as they are missing pipeline coverage targets, I believe this is a pipeline crisis, and not a conversion rate crisis.

The struggle is real.  If you’re facing it, you are not alone.

Against this cacophony we hear a lot of talk about “brand vs. demand.”  The argument being that since demand generation programs are working less effectively, marketers should increasingly allocate dollars to brand programs.  It’s not a bad argument — in part because I believe that marketers over-rotated to highly measurable marketing during the go-go days — and thus a swing back to less directly measurable marketing is a good idea. 

(Aside:  I’d argue that marketers didn’t over-rotate on their own.  They got an assist from CEOs and CFOs who were only too eager to invest exclusively in marketing programs that delivered a clear short-term return and ignore the underlying complexity in B2B sales, effectively living-the-lie that is marketing attribution.  We don’t sell toothbrushes here, people.  Nobody goes to a tradeshow and buys a $250K enterprise solution — or even a $25K one — based on one interaction with one person.  But I digress.)

The question, of course, is what to do about it?

What Others Are Saying

A lot of smart people are weighing in, so I thought I’d provide a few links before sharing my own take.

  • Kyle Poyar wrote a great post called The 2025 State of B2B GTM Report.  (Subtitled “What’s Working in GTM?  Anything!?”)  My favorite part is the GTM Scorecard, a quadrant that maps channels by popularity and likely impact.  The underlying report is full of good ideas, GTM tool recommendations, and survey data.
  • The aforementioned Exit Five post, despite its title, is actually about what is working with answers derived from an informal poll of community members.
  • Scale recently published a State of GTM AI report which provides survey data on AI within GTM, focused largely on high-level use-cases and a two-phase adoption model.  (Jadedly, if we’re going to do less effective work, then let’s at least do it more efficiently.)
  • If your issues are more strategic, such as identifying and targeting sub-verticals, then you should read my friend Ian Howell’s book, Smart Conversations.

What Would Dave Do?

I’m going to build upon a popular comment I made on Kyle’s CAC payback period post.  Consider this a sister post to What To Do When You Need Pipeline in a Hurry, but this time not focused on the hurry, but on today’s environment.

Here’s what I would do:

  • Think holistically.  You might only be the CMO, but you need to look across all pipeline sources.  The job is to start quarters with sufficient coverage and notably not just to hit marketing pipegen goals.  If outbound is working, reallocate money to it.  If AEs can generate more pipeline (e.g., formal targets, more direct routing of inbound), then do it.
  • ABM.  Substitute across-the-board campaigns with targeted outreach on key accounts, leveraging both marketing and human channels (e.g., SDRs), both digital and dimensional assets (i.e., physical things like branded Moleskines), and intimate live events.  As an old CRO friend says, “if by ABM you mean us picking our customers as opposed to them picking us, then I am in favor.”
  • Events.  People are tired of working from home all day and champing at the bit to get out and press the flesh.  This includes major tradeshows, annual user conferences,  and roadshows all the way down to field-marketing dinners and sporting event boxes.
  • Get good at AEO.  It’s quickly replacing and more effective than search.  It’s also more winner-take-all.  There is plenty of content out there on how to do it and agencies eager to help.  Read these two articles for starters.
  • Leverage the CEO via social media (e.g., LinkedIn), podcast appearances, and speeches.  And LinkedIn doesn’t just mean a few posts, it means an overall strategy.
  • Use your AI message to put butts in seats.  We’re still in the stage where people are confused about AI and nothing puts butts in seats like confusion.  Do educational webinars, videos, and content.  Educate people but be sure to do it en masse.
  • Leverage AI tools and workflows.  Review Kyle’s report, particularly the part on the GTM tech stack.  Read Paul Stansik’s practical posts on AI, including how to avoid slop.
  • Build first-party audiences.  If you can no longer pay a reasonable amount to reach other people’s audiences, then you’re going to need to build your own.  While this is a slow burn, over time you’ll be happy you did it.  Build a Substack, a YouTube channel, a quality newsletter, or a podcast.
  • Leverage partners.  They can account for 20-30% of your pipeline and usually bring opportunities that close faster and with a higher conversion rate.  If you have a partner program, leverage it.  If you don’t, start building one.  It’s another slow burn, but you’ll be happy you did it.
  • Check your nurture tracksLong-term nurture is easily forgotten.  Measure recycled leads.  Report on your tracks.  Ensure you’ve built specific tracks for competitive loss and bad timing.  A/B test them, the flows, and the content.
  • Understand why you lose.  While I believe most companies have a coverage problem, not a conversion problem, I like to win anyway and if your conversion rates are below 20-25% you need to understand why.  Do quantitative win/loss via CRM reporting, listen to call recordings, and do win/loss interviews to understand what’s really going on.
  • Invest in customer success.  While I know this doesn’t help with pipeline coverage (except for expansion), always remember that the cost to backfill churn is CAC-ratio * lost-ARR.  Thus, if your CAC ratio is 2.0 and you lose $2M in ARR, it’s going to cost $4M to backfill it. The easiest – and most cost-effective — way to keep the ARR bucket rising is to limit leakage.
  • Join a community.  In times of change it’s important to have colleagues you can talk to, so I’d not only keep in close touch with existing peers, but join a marketing community like Exit Five to engage in shop talk.

The Startup Board’s Hippocratic Oath

The Hippocratic Oath is a well known oath of ethics taken by physicians. It requires them to swear, among other things, to do no harm in dealing with patients. While chatting with a VC the other day, it occurred to me that we should have a similar concept for startup boards.

Unfortunately, I think “do no harm” actually sets too high a bar.

To help startups succeed, boards need to challenge leadership teams, ask hard questions, and get them to consider new ideas and approaches. While I think boards should refrain from giving directive feedback, there is always the chance that a hard question leads the company down a path that ultimately proves unproductive. For example, if a board member asks if a company to consider a PLG motion for a new product, that could lead to the company launching a new sales motion that ultimately fails.

This example, by the way, shows both why boards should not give directive feedback (i.e., “do a PLG motion”) and why founders should not listen to them when they do. Think: yes, we’ll consider that, but only try it if we think it’s a good idea. Throwing a bone to board members by agreeing to try ideas you don’t believe in is a losing strategy. If they fail, you are more likely to get scorn for poor execution than credit for the openness in having tried. When results are the only thing that matter, only place your bets on things you think will deliver results. (And yes, the possibility that you threw good execution at a bad idea seems conveniently never to be in consideration.)

If “do no harm” sets too high a bar, then what oath might we use? After talking to my friend, I think I found a great alternative: do no demotivation. “I don’t want executive teams leaving board meetings feeling demotivated,” he said. And he was absolutely correct.

How do we want people to feel at the end of a board meeting?

  • We want the board to feel like they attended a well-run meeting, had a chance to help the company, and understand the plan to address current challenges going forward
  • We want the management team to feel like the board is knowledgeable, helpful, and supportive
  • And we want the management team to feel energized to go execute the plan

That’s it. If you get those three things, you had a successful board meeting. And demotivation is nowhere on that list. Demotivation doesn’t help anyone.

  • It doesn’t improve the odds of executing the plan successfully
  • It definitionally doesn’t make anyone feel good
  • It does make the e-staff start to question the CEO and each other
  • It does make people wonder why they’re grinding so hard
  • It does make the team feel unappreciated and potentially vulnerable

So I’d propose Do No Demotivation as the Hippocratic Oath for startup boards.

I’ll finish this post by listing some common ways that boards demotivate executive teams (and feel free to put more examples of your own in the comments):

  • Expressing surprise over things they should have known.
  • Asking trap questions: “do you think our sales productivity is substandard or very substandard?”
  • Placing blame: “clearly, since our CAC payback is so long, we have an inefficient sales organization.” (Maybe we do. Or maybe we have a hard-to-sell product. Or weak gross margins. Or something else. The high CPP is a fact. The reason for it is not always a bad sales team.)
  • Cherry-picking: taking top decile benchmarks, or public comps, or even just top quartile numbers but across 4 different metrics. It’s like comparing your child to the best mathematician, athlete, musician, and writer in the school. (It’s quite rare when one person is all those things.) Or, my favorite: benchmarking without regard for situation. Yes, our CAC ratio is high, but 75% of our deals are dogfights against a price-slashing competitor. And yes, I know what “sell value” means, thanks.
  • Expressing anger in pretty much any form. While I’ve seen some howlers, fights in board meetings are not OK. They demotivate everyone. And they take focus off the top busness priorities.
  • Ratholing, failing to take things to an offline meeting or working group. OK, I do this one from time to time. (“But I promise it will be quick.”)
  • Making easy things hard. When in doubt, if a topic is not strategic, just do things the standard way at the good-enough level.
  • Expressing negative or hopeless sentiments: “at this course and speed, I’m not sure we’re creating any value.” As opposed to: “we need a new plan that creates value and that means we need to find a way to accelerate growth.”

So before you attend your next board meeting remind yourself to do no demotivation. It’s the new Hippocratic Oath of startup boards.