Category Archives: Sales

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.

Slides From My SaaS Metrics Palooza 2025 Session on Selling Work vs. Selling Software

Today, I presented at SaaS Metrics Palooza 2025 on the differences between selling work and selling software. I’d like to thank my metrics brother, Ray Rike, for inviting me to speak and I’d like to thank everyone who attended the session.

Topic covered include:

  • Defining outcomes
  • Contrasting outcomes vs. usage
  • The outcomes stack and intermediate vs. end outcomes
  • How a dating site would price based on outcomes vs. subscriptions
  • The basic trade-offs in selling subscriptions vs. outcomes
  • How to capture value created and share it between the vendor and customer
  • How selling outcomes can (radically) expand the total available market (TAM)
  • Jevon’s Paradox and what happens when we make things radically cheaper
  • Selling virtual humans vs. jobs-to-be-done
  • A long list of links to references for additional reading

You can download a PDF of the slides here. You should be able to see a recording of the session here. (Frankly, I’m not 100% sure that link will work, but you can try.) And I’ve embedded the slides below.

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.

Whence Will Come Tomorrow’s Sellers?

To the extent that most sellers today started their careers as SDRs and to the extent that there is a strong trend to replace SDRs with AI agents (e.g., Piper from Qualified), I have a simple question: whence will come tomorrow’s sellers? [1]

It’s not news that this is a trend across all entry-level work, though I just found a new paper on the topic by three people at Stanford who examined ADP payroll data as the basis for their analysis: Canaries in the Coal Mine? Six Facts about the Recent Employment Effects of Artificial Intelligence. And another one that analyzes resume and job posting data: Generative AI as Seniority-Biased Technological Change: Evidence from U.S. Résumé and Job Posting Data.

But in today’s post, we’re not going to look globally at the topic — no matter how interesting it is — but instead look specifically at just one question: if all the SDRs are AI agents, then where are we going to get sellers from?

I should also explain that I have a dog in the fight. My son Brian just graduated from NYU and started this summer as an SDR at Ramp. (If you’re a US-based company with 150+ employees and interested in spend management, please let me know and I can connect you.) I recommended that he take the job because it’s an amazing company, they have built an excellent sales machine (and the early-career learning on how to do things right is invaluable), and he definitely has both the raw material and the mettle to be successful in technology sales. But as I made the recommendation, I couldn’t help but wonder if he’d be in the final cohort of human SDRs.

My question actually has two parts, so let’s take them one at a time: (i) an assumption that SDRs will be replaced with AI agents, and (ii) the realization that doing so would seriously interrupt the sales career development pipeline.

Will All SDRs Be Agents?

I think the answer here is no, though I do think a good number of them will be. One easy division is inbound vs. outbound. Inbound SDRs primarily qualify and route people with intent (“hand raisers”) to sellers for a discovery and qualification meeting. Input: MQLs. Output: stage-1 opportunities. Outbound SDRs focus on some set of target accounts and work them via outreach sequences in order to get them to take a meeting. Input: contacts. Output: stage-1 opportunities. While they might also receive MQLs from their target accounts, they start higher in the funnel and are more responsible for developing interest in a meeting than someone who downloaded an asset, like it, and wants to speak to a seller.

I believe inbound SDRs provide less value than outbound SDRs and their job is more automatable. Ergo, I think inbound SDRs will be quickly replaced by AI or superannuated by targeted, hybrid inbound/outbound models (i.e., my job is to get into Citibank and I’ll take all the names, leads, and MQLs we have and leverage them to get meetings within the account).

I think outbound SDRs are here to stay. And Ramp, for what it’s worth, seems to agree. I know they’ve onboarded another cohort since Brian’s and they seem to believe that their SDR model works quite well for them. So if the old career path was inbound-SDR into outbound-SDR, I think the new one will start with a hybrid. You’re just an SDR and your job is to get meetings within some target. Sometimes you’ll have a lot of inbound interest to work with, sometimes you won’t.

The first-principles argument here is simple. When automated outreach sequences are table-stakes that every firm can easily do, the only way to break through the AI-generated and AI-automated noise will be via some combination of people/execution, message, and air support [2]. That’s why we’ll still need SDRs — and good ones — in the future.

Where Will We Find Tomorrow’s Sellers?

Since I believe there will be SDRs in the future, I think we’ll find our future sellers there. But in case that’s wrong, let’s examine where we might find them additionally or instead. I’m old enough to remember life before SDRs. So where did we find salesreps back then and where might we find them in the future?

  • Junior sales roles. You’d work your up from smaller companies to bigger ones and from managing smaller accounts to bigger ones. This should still work.
  • Sales training programs. Some companies were famous for their sales training programs, like Xerox or IBM. I’d differentiate those who emphasized entry-level sales training from those who hired sellers with some experience and who emphasized sales onboarding in a particular message or methodology (e.g., Salesforce, PTC). In the future, large companies who find themselves with a talent gap may need to create such programs, substituting Darwinian survival in the SDR ranks for a formal, and presumably demanding, training program. Once established, these companies will be targets for everyone else’s recruiting.
  • Sales consultants. A difficult path but those who survive the transition are often your best sellers. Everytime I hear an SC complain about salesrep compensation, I say the same thing: “quotas are available.” Go grab one and see how you do. (Or don’t and stop complaining,)
  • Customer success. I think this is an under-developed career path and hopefully, as CS gets more business-oriented and account-management-focused, that customer success will be more of a stepping stone into sales. Think: I developed my prospecting muscle as an SDR, I developed my closing and account management muscles as a CSM, and now I’m ready to be a salesrep.

As the SDR ranks shrink due to the pressure brought by AI, companies will have to be more creative about where they find their salespeople. Some will certainly walk up the SDR path. Others, the junior sales path. Some, the top sales training path. But I don’t believe there will be a shortage of sellers in the future. Just a shortage of good ones, as there is today.

# # #

Notes

[1] Turns out that while both “whence” and “from whence” can be considered correct, technically standalone whence is still better in my humble opinion because whence means “from where” so “from whence” is, well, redundant.

[2] In the form of marketing, awareness, reputation, brand, etc.

Your ICP Starts as an Aspiration and Becomes a Regression

The concept of an ideal customer profile (ICP) has been around for a long time, but like its cousin, the minimum viable product (MVP), it is often misunderstood. In this post, I’ll offer some background commentary on the ICP concept and then build into one of my favorite sayings: your ICP starts out as an aspiration and becomes a regression.

There are four common questions around ICPs. Here they are, along with my answers:

  • Is the ICP about a person or a firm? Both. It should include firmographic as well as role (or persona) information. Example: VPs of sales at technology companies between $500M and $2B in revenues. Here, we included the size and industry of the company along with the target buyer’s title.
  • Should an ICP include a problem to be solved? Yes. VPs of sales have lots of different problems from recruiting to training to pipeline management to forecasting, just to name a few. Thus, your ICP should include the ideal person at the ideal company and the problem you’re looking to solve for them.
  • Should the ICP include adjacent systems? Yes. Deciding at the outset if you want to focus on customers using specific, adjacent systems is often critical (e.g., NetSuite vs. Oracle vs. Xero for core financials, Salesforce vs. HubSpot for CRM). The alternative is drowning in integration work while never having the time to support the idiosyncrasies of a given package which, when you do it, is usually adored by customers.
  • Should an ICP include sales qualification criteria? No. The ICP is about the buyer: this is the person we’re looking for. They have this job at this kind of company. Whether they’re out shopping right now, whether they have budget, whether they have a buying timeframe and purchasing authority are all important qualification questions, but they are not part of the ICP itself. People differ on this, I know [1].

Because the world is imperfect and it’s difficult to find “Mr. or Ms. Right” every time, it’s useful to think of the ICP as a bullseye. The absolute perfect customer is in ring 0, the next level off in ring 1, after that ring 2, et cetera. Note that I have no religion about the things you vary across the rings, but the usual candidates are: job title, industry, size, adjacent systems, and problem (aka use-case). And you might do them in unusual combinations. For example, if you think a director of finance with a budgeting problem is about as good as a manager of finance at a bigger company with an operational reporting problem, then you can put them both in ring 2.

The idea is to give you a simple and flexible model to agree on who to target and who to prioritize across sales, marketing, and product.

For a zero-to-one startup, you might focus exclusively on ring 0. As you grow you will typically get more use-cases, more industries, more adjacent systems, and thus more rings. That’s fine as long as you’re defining the rings clearly and triaging them into: hot pursue, pursue, and slow-roll or some similar encoding system.

With a few clearly established tiers you are now ready to report on ARR and pipeline by ICP tier to see if “you’re walking the talk” when it comes to your ICP. At many companies, you will find the majority of the ARR and pipeline [2] outside ring 2 or 3. In these cases, you simply aren’t living your ICP and instead suffering from a faux focus. The usual cause is an inability to control the sales force and prevent their default “chase anything” behavior [3].

The ICP is typically born in the founder’s head as an hypothesis. Think: I bet if we can build something like this, it will solve a problem like that. By the time a company has been founded and a product built, it becomes an aspiration. Think: I want to sell to people like this to solve a problem like that. So you sharpen your definitions of this and that, and add some additional targeting criteria like company size, industry, or adjacent systems. And then you go off and sell.

Let’s say it works. One day you look up and you’re now $50M or $100M in ARR. Congratulations. Should your ICP still be an intuition-driven aspiration? No. It should be a regression. Reality happened. Let’s find out what reality is telling us.

Are the people in our ICP ring 0 really our best customers?

Well, what do we mean by best? Do they have higher ASPs? Do they have shorter sales cycles? Do they renew at higher rates? Do they expand at higher rates (e.g., NRR)? Do we win new deals at higher rates? Do they give us higher CSAT scores?

At the first order, these are all just simple segmented metrics calculations that you can and should do. Your QBR and board decks should show these key metrics segmented by ICP tier [4]. And — since not all these metrics can be important — your e-team also needs to have the conversation about “what do we mean by best” so you can have a common, precise definition of the “best” customers that you are trying to target [5].

But the best answers to these questions are not performed using segment analysis [6]. Segment analysis is great for finding anomalies — e.g., why do we have a higher win rate in ICP tier 3 than tier 1? But it’s not a great technique for actually finding the impact of different variables on the success criteria.

For that, we need regression analysis. Regression analysis will tell us which variables most strongly correlate with the outcomes we want (e.g., that the strongest predictor of renewal is company size, not CSAT) [7]. A good regression analysis will tell you not only which factors most correlate with the outcome, but it can also be the best way to bucket those variables (e.g., the real breakpoint is at 250 employees, but your initial segment went from 0 to 500).

Odds are, when we do this kind of analysis we’ll find lots of surprises. Some of your intuition will be proven correct, but some won’t. And you’ll likely find entirely new variables (e.g., number of data scientists) that you didn’t even consider in your initial ICP exercises.

So this is why I like to say that your ICP starts as an aspiration — about who you want to sell to — and over time becomes a regression. Because one day you will have lots of data to analyze to determine who your best customers are — subject to your definition of best, of course — as opposed to who you thought they would be.

# # #

Notes

[1] Regardless of where you land at least be aware there are two types of criteria: those that change slowly or not at all (e.g., company size, adjacent systems, industry) and those that can change overnight (e.g., out shopping, budget, authority). My analogy here is dating: you can meet the right person at the wrong time. It doesn’t change the fact that they’re the right person. (And that’s why God made nurture tracks.)

[2] Think of pipeline as a potential leading indicator of ARR. Well, it should be, at least.

[3] Using the ICP in territory and compensation plan definitions can help with that. Think: you only earn commissions on customers in ICP rings 1 through 3 within your geographic territory. That will get your sellers’ attention.

[4] Note that I’m kind of using ICP tier and ring synonomously here and that’s generally OK. However, in cases where you have lots of rings, I would then sort those rings into tiers, so ring is the more specific and tier the more general term. For me, because I like simplicity, I want to see ICP segmentation in at most 3-4 buckets, so if there are N rings underlying those, I’d prefer to hide those by using 3-4 tiers.

[5] You probably don’t want marketing targeting high LTV prospects when sales wants to target high win rate ones. We should all be on the same targeting page.

[6] One of the key problems being that the segments themselves were somewhat arbitrarily chosen. Sure, we did our best to guess who’d be our best customers. But who are they actually? We may have used not only the wrong bucket boundaries (e.g., 100 emps vs. 500 emps) but even the wrong dimensions (e.g., maybe company size is a poor predictor and industry or use-case a powerful one).

[7] I cheated here on purpose to see if you were paying attention. Thus far, we’ve largely said the ICP is about a company (firmographics) and a role/persona. But here I’ve said that company size is a better predictor or renewal than CSAT — and CSAT isn’t a ICP-style criteria. The reality is these tools can do precisely that, looking across a wide range of input variables to see which most influence the output. Obviously, for marketing targeting purposes we don’t want CSAT to be an input variable to the model, but for renewals analysis we sure would.