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Most revenue problems aren't growth problems. They're foundation problems.
In this episode of GTM Uncensored, Adam Jay sits down with Revenue Reimagined co-founder Dale Zwizinski to unpack what broken revenue organizations actually feel like from the inside.
From messy CRM data and unrealistic board expectations to broken customer handoffs and misaligned teams, Dale explains why growth can't fix weak foundations. They also discuss why customer success should be treated as a revenue function, how leaders can identify root causes, and why slowing down often leads to better decisions.
Adam and Dale discuss:
- Why more SDRs won't fix a broken pipeline
- Resetting a bad forecast in week one as CRO
- Turning the sales-to-CS "handoff" into a "handshake"
- What the NRR vs. GRR gap really tells you
- How shaky foundations and yes-people sink companies
Chapters:
(00:00) Introduction
(00:27) Handling bad CRM data and unrealistic forecasts
(05:29) What coding taught Dale about go-to-market
(08:56) Why data needs to be digestible
(10:12) Why RevOps matters after $5M ARR
(11:46) What broken revenue organizations feel like
(14:00) The real cost of a broken CS motion
(16:44) Why handoffs should become handshakes
(19:23) Customer success metrics that matter
(21:41) Are your CS reps really just schedulers?
(23:05) Telling founders what they don't want to hear
(25:18) Why most companies are building on shaky foundations
(26:51) Dale's most expensive mistake
(28:16) Why great leaders pause before reacting
(31:41) Closing
Creators and Guests
What is GTM Uncensored™?
Most GTM content covers the same ground. GTM Uncensored finds the operators actually in the seat and digs into what's true in today's GTM, not what sounds good.
Every guest is currently building a company, leading a revenue team, or running a GTM function inside a real business. During the show, Adam and Dale push the envelope until the real story comes out.
The show goes where most content won't: The motions that determine whether a company stays in business, or goes under.
GTM Uncensored is built for B2B revenue leaders at $5M–$100M ARR who are accountable to a number and need a real-world playbook, not philosophy.
Every episode ends with a Monday Morning Move. One specific action you can take this week, and a series of Uncensored Questions where listeners get unfiltered answers from people who've actually been there.
What we cover: Pipeline & GTM motion, post-sale architecture, CS & retention, NRR/GRR mechanics, RevOps, AI in the revenue org, executive branding, and more.
Your hosts: Adam Jay and Dale Zwizinski are co-founders of Revenue Reimagined. They didn't build a consulting firm. They flipped the fractional CRO model because strategy without execution doesn't move the needle. The questions they ask on air are the same ones they're solving inside real companies right now.
GTM Uncensored is the GTM conversations nobody else is having.
(00:00) Dale: I think a lot of people just go into, "I want more top of funnel." And it's like, great, you want more top of funnel, but to get more top of funnel – go hire more SDRs, for example. That's their mindset. Okay, but to go get more SDRs, now you've got to think, "Do I have the right job description? Do I have the right onboarding process? Do they understand what the value proposition is?" There's a lot of other things involved beyond just hiring new people.
(00:52) Handling Bad CRM Data and Unrealistic Forecasts
Adam: All right, dude, here's the question. You just got hired. You're the CRO. It's a $25 million company. You uncover that there's three years of bad CRM data. You have the board down your throat saying, "We've got to have a forecast in a week. We have our quarterly board meeting, we've got to have a forecast." And it's got to be right because your job depends on it. Where the hell do you start?
Dale: Yeah, I think there's two things. One is I need to really figure out from the CEO or the founder, whoever it is, what number they actually presented to the board, how they presented it, and what the caveats were. And then what I would do is look through the data to get a level set on where we stand today.
Dale: And then I would say to the CEO, "We would have to build out a plan together to say, 'I know you presented this to the board. This is not really what we need to do. We probably need to recast this number.'" And then what I would do is use some kind of AI technology – like Claude – to go through the CRM and find out where some of the real data is.
Dale: And while I could give a draft pipeline and number, I would caveat it as, "I've only been here for a week. We need to figure out exactly what that number is. We probably haven't done a bottoms-up model – what is the actual number?" And try to find out from the board why that number is so important to them.
Dale: So have that conversation with the CEO, and understand why we've given this unrealistic number to the sales organization. Once I've had that conversation with the CEO, I would actually put the board on notice a little bit and ask, "Why did you guys agree to this number?"
Adam: Whoa. Let me get this straight. You've been there for a week and you're going to put the board on notice?
Dale: There's a reason why they hired me as a CRO – because they know that it's broken. They know that what they're doing is not realistic. So we all need to get on the same page. If I just take their number and say, "Okay, that's realistic," I have no clue whether it actually is.
Adam: How do you push back without making your 18-month tenure 18 days?
Dale: I think you just have to understand the why. Why are we doing this? And then if that number is really that important to them – if they've committed it to someone else or they need to sell the company within 24 months – there's a reason why we have this number. And if they can't come up with a good reason, that's a telling sign.
Adam: Why didn't you come up with that reason during the interview process?
Dale: Because I didn't have enough data points. You need to get into the data first. It could be fine – you want that number? Then we have to go hire four more enterprise reps, ramp them up, and go through the entire process. There are reasons why they want the number.
Dale: And I've done this with many boards. We just go in and have a conversation and I say, "Look, we will get as close as we can to the number, but here's the realistic number. Here's the pipeline, here's the analysis and capacity. You're coming at it from a top-down perspective. Let me give you a bottoms-up perspective and let's come to a middle ground."
Adam: But why are boards afraid of the bottoms-up model? Other than the fact that it makes their whole model fall apart because they realize they can't achieve what they want with the people they have?
Dale: I don't think they're afraid of it. I think they don't understand it. I think they haven't truly digested it. It's just the way they've always done things – "We need to grow 20%, so put 20% on top of last year's number," without accounting for any of the variables.
Dale: There are broken things that need to be evaluated – ideal customer profiles, buying personas, all of it. Because you brought me in for a reason. What was happening wasn't working, so why are we just going to keep doing the same thing? That's the definition of insanity – doing the same thing over and over and expecting a different result.
Dale: I would have that conversation whether they liked it or not. And I wouldn't take the job, by the way, if the CEO didn't have my back. If the CEO wasn't saying, "I trust you and I believe in you," then why am I there?
(04:57) What Coding Taught Dale About Go-to-Market
Adam: All right, let's shift gears. One of the things I love most about you is also one of the things I find most challenging – your background in coding. Prior to entering the sales world, prior to entering the SE world, most people don't know this, but you actually coded, you developed.
Dale: I did.
Adam: I'm grateful for it because of everything we're building with AI. But I think it makes you much more analytical. One of the things you've really taught me is the value of saying, "I need to sleep on it, I need to think about it" – and I think that's very much the coder in you. But what did coding teach you about go-to-market that most go-to-market leaders, even myself, will likely never fully learn?
Dale: I think it's understanding that you need to build the proper spec and define what you actually want to deliver. There's a plan you need to build out, and within that plan are a series of steps, and underneath those steps are very tactical things you have to do. A lot of people just say, "I want more top of funnel," without thinking through the actual mechanics of how to get there.
Dale: It's that domino effect. I remember the first time I was coding in a lab, typing it out, and "Hello, world" came up on the screen. I thought, "That is the coolest thing." I feel that same excitement now with AI. In the AI world, you as a businessperson have way more control over what you really mean because you get instant feedback.
Dale: In the development space or even in go-to-market, if you say, "We should change up our value proposition," and start changing your email content, your outreach, and your website – you don't get feedback for three months. And people don't want to wait 90 days. They want feedback in 90 seconds. That's what the new AI world gives businesspeople – the ability to have instant feedback and understand, "I know what I said, but that's not what I meant."
Dale: Coding is very black and white – ones and zeros. Everything else becomes shades of gray. We need to get away from shades of gray and get very specific about how we're doing things.
Adam: It's not the ones and zeros, but it's also not the vague "I want more top of funnel." You have to get very specific about the goals you're trying to accomplish. I find that people don't set goals well. What do you actually want to accomplish? We do this all the time in our go-to-market sprints.
Dale: It's what are we accomplishing in the next 30 days?
(07:57) Why Data Needs to Be Digestible
Dale: How many times have we set a goal in a sprint at the beginning of the month, and by the end of the month we're in a completely different place? We're deviating, going to other areas, finding different problems. But in those different problems, you have to identify the root cause – because if you don't get to the root cause, you're solving for something that won't actually fix the real problem.
Adam: So let's talk a little bit about root cause, data, and solving problems. We have more data at our fingertips than ever before – CRM data, RevOps data, AI tools data. What are people getting fundamentally wrong about how data should actually work to drive the decisions that move the business forward?
Dale: That's a really interesting question, because we always wanted more data. The problem is the data isn't digestible. And we don't always trust the data. Until you build trust in the data – just like you'd build trust in a person or in AI – you're not going to use it effectively.
Dale: Then you need to get it to a place that's digestible. The way we present data to the board is completely different from how I present data to my team, which is completely different from how I present it to the marketing group. Same data, but you have to make it digestible for the audience you're speaking to.
Adam: How do you actually do that though? How does a go-to-market leader who isn't a data expert – and maybe that's part of the problem – make data digestible? And can you do it yourself, or do you need a so-called "AI tool"?
(09:35) Why RevOps Matters After $5M ARR
Dale: I think, depending on where you are in your revenue cycle, you really need a RevOps person who can find where all this data lives. The problem isn't the data – the problem is whether you're getting the right data in the right place, in a format that you as a revenue leader can actually digest and then articulate to the board, the team, and your peers.
Dale: If you're getting to $5 million in ARR and you don't have a RevOps person, you're falling behind. The first $5 million, it doesn't really matter – you're trying to get revenue, you're trying to get top of funnel, you probably have the wrong ICP.
Adam: Throw stuff at the wall and see what sticks.
Dale: Right. But once you hit $5 million, you should have your systems in place, your data in place, and the foundational layers built out. Because prior to that – going back to the go-to-market gap – it's complete chaos. You've got to stabilize it and then build the foundation. And in that foundation-building is the world of revenue operations.
(10:57) What Broken Revenue Organizations Feel Like
Adam: If I'm running a company, $5 million – or even four or five million – is the right inflection point to start thinking about structure and foundational pieces. All right. What does a broken revenue org actually feel like from the inside? You've been there, I've been there.
Dale: How the hell do I get out of here? But beyond that – if the CEO understands that things are broken and is okay with the modifications and changes that need to happen, it starts with a level-set conversation: "We talked about this during the interview process, but here's the reality of what's actually happening."
Dale: It happens to us all. We come in and we've been told, "Oh, there's tons of pipeline, tons of opportunity." Then we do a pipeline analysis and find nobody's touched a deal in six months. You talk to the rep and they say, "That's not happening." And you wonder, why is it even in the pipeline?
Dale: You go through the whole thing and there's so much tension in the organization. It feels sticky. It feels like you're in mud – you can't make any movement. And it feels like everyone is laying political landmines trying to catch you out.
Dale: And it's very hard to build any momentum. If marketing isn't aligned to you, if marketing has a different revenue goal or perspective, then you're battling with them, and potentially battling with the CEO, and everyone's trying to get everyone else fired.
Adam: Toxic. That's it. In every broken revenue org I've been in, what it feels like – you touched on it – chaos, silos, infighting, everyone out for themselves. No one has each other's back.
Dale: Yep.
Adam: I've worked with marketing leaders where regardless of whose fault it is, it's, "Listen, we collectively made a mistake and we collectively need to fix it." It's a go-to-market unit. In broken orgs it's, "This is a lead problem. My team is doing everything they need to do." But when these orgs are broken, certain stages of the customer journey are consistently being underestimated. Where do you see it breaking most? And can you attribute a cost to it – even a soft cost?
(13:32) Where Revenue Really Dies
Dale: I think the biggest cost, especially for revenue orgs at $5 million and above, is on the customer success side. Your customer acquisition cost is so high in a lot of these companies because it's hard to get people in the door. If you're trying to patch the boat from the back end, it's going to cost you time, money, and reputation.
Dale: All of a sudden you become irrelevant. And the other thing I'm seeing right now is this whole world of the SaaS reckoning – moving away from seat-based pricing, all of the changes happening on the SaaS side. I heard a podcast the other day that said people are buying SaaS companies at one-and-a-half times revenue specifically to convert them into AI-native applications. The seat-based pricing model is going out the door.
Dale: So what is the real cost of not knowing your market, not understanding your ICP, not understanding your Gross Revenue Retention? These are the things that serious buyers are scrutinizing, and there are sharks in the water looking for blood.
Adam: You just touched on CS, and I do agree that CS is where I see a lot of broken things. But I think it starts with the sales-to-CS handoff. That's where revenue goes to die in a lot of companies.
(14:57) Why Handoffs Should Become Handshakes
Dale: I think what people are calling a handoff isn't actually a handoff. How can we fix that?
Adam: This is consistent across the majority of companies we've worked with and worked for. That transition has always been a problem. What has to be true on both sides to fix it?
Dale: The first thing is we've got to drop the word "handoff" and replace it with "handshake." In a handshake model, CS is part of the end of the sales process. There's overlap – it's not "I have a customer, now I'm passing them off to you." That feels bad for the customer too. Who wants to be handed off?
Dale: Even better – if the customer didn't like their sales rep, are they automatically going to like their CS rep? So if you bring the CS person in at the proposal stage – when you're going over a proposal with your client and you bring in the CS person who would potentially be assigned – they're listening to the proposal, hearing the customer's questions, understanding the problems being discussed. Now you start building the handshake.
Dale: When we close the deal, the customer has already seen this person, they know their name, and the CS rep can start speaking their language from day one. Just like we try to do all the research at the top of the funnel to understand a prospect before we reach out.
Adam: The top-of-funnel handoff is broken in most orgs too. I never want to talk to a BDR, go through discovery, get approved, and then have to start all over again with an AE. That is the most frustrating experience.
Dale: Totally agree. And I actually think that top-of-funnel breakdown could potentially start with marketing as well – if we're not bringing in the right leads or the right value proposition. That's the other piece of the handshake: CS people need to understand the impact that we're selling. If we're selling software at $100K, what's the impact the customer is actually buying it for?
Adam: Most CS people are measured on renewal rates. I'm a big believer – and I think you are too – that CS teams are a revenue function. So if we call CS a revenue team and we're doing a handshake, not a handoff, what does that scorecard actually look like? What should they be measured on that most dashboards aren't showing today?
(17:28) Customer Success Metrics That Matter
Dale: Yeah. I think there are two primary metrics they should be measured on. One is NRR – Net Revenue Retention – which captures the expansion revenue running above the baseline. The other is GRR – Gross Revenue Retention – which is the renewal rate.
Dale: The interesting thing about GRR is you can never exceed 100%. NRR, on the other hand, can go well above 100%. We've had clients where NRR is at 150, 160, even 170%, which is fantastic – that's a true land-and-expand motion. And once you know you have a land-and-expand motion, you can bring that insight back to sales. Sales can then build a motion around, "We don't need to sell $100K deals on day one. We can sell $10K deals that grow to $100K."
Dale: But if NRR is at 150% and GRR is at 85%, there's a juxtaposition – you're expanding a lot of accounts but also losing a lot of accounts. That could mean a lot of different things: the product isn't what was described, it wasn't the right ICP, sales oversold, or CS isn't doing their job. There are so many interaction points across the entire go-to-market strategy.
Dale: And when we're losing customers or not renewing them, that information needs to loop back to the product team, the marketing team, and the sales team. I don't think that loop is being closed nearly enough.
Adam: I agree. I think there's a fundamental CS problem. And that takes me to this week's Monday Morning Move. It's fairly simple: if you're unsure what your CS team is actually doing and what they're measured on, look at their calendar. Count how many hours are admin, notes, check-ins, CRM updates, QBR prep. If it's more than 50%, you don't have a CS team – you have a scheduling team. And the fix is the systems, the processes, and most importantly, the job description.
(19:56) Are Your CS Reps Really Just Schedulers?
Dale: Yes, 100% agree. And I'd add one more thing. I'm a big believer in having a brief meeting at the start of the week and a quick wrap-up at the end. Set up your week on Monday – a quick conversation, a Slack message, whatever – and have your CS reps outline who they worked with, which clients, what challenges came up, and how you can help them do better.
Dale: You can simply ask, "What are the things you're working on?" And it feels like 20 hours of work when they start listing things out. You wonder what happened to those 20 hours. Then they start sharing all this other context. And if that becomes the norm, either we have a broken process or we have a broken individual. We need to fix whatever the root problem is.
(21:06) Telling Founders What They Don't Want to Hear
Adam: I want to get a little spicy. Tell me – and not a story you've already told me – about a specific time you had to tell a founder something they really didn't want to hear. What was it, and more importantly, what happened?
Dale: Yeah, actually this was before I even got hired. I basically told this founder, "You can't afford what you're trying to get into." They only had a couple of million dollars in revenue. And I told them, "You should bring in a fractional leader here. I don't want to come on full-time. It doesn't make sense – it's not going to work out well because you need to get some foundational pieces set up first, then let's revisit."
Dale: Their response was, "No, my board wants a full-time hire." I heard that and thought, okay. So I ended up going in full-time. And three months later, same story – the pipeline wasn't there, we were starting to build, I was putting in all the foundational pieces, but the writing was on the wall. They didn't have enough runway to sustain it.
Adam: But you still took the job?
Dale: Yeah, because I believed in the product. When I was talking to the CEO, it was "I have this product, I have this prospect, I have this prospect." I went through the CRM and thought, okay, there's something here. But then when I talked to the sales reps later, nothing was actually happening. They couldn't get people to respond. That's what I learned to ask about in interviews.
Adam: I fell for a product that was basically a giant Figma demo, which is a whole other story.
Dale: It was a great Figma demo though.
(23:06) Why Most Companies Are Building on Shaky Foundations
Adam: All right. Let's get into our uncensored questions. Revenue Reimagined is literally the company name. So talk to me – what's broken about the way revenue actually works? What are most companies fundamentally getting wrong?
Dale: I'll always come back to foundational. You've got to build the foundational pieces. We're building things on top of shaky foundations and then wondering why things aren't working.
Dale: The biggest issue is people think they're solving a problem and then they put it on a shelf. You solve a problem, then you reiterate. You solve a problem, then you iterate again. You've got to keep doing it quickly. That's the first thing.
Dale: And then the second thing is: tear down all the silos. Forget everything you've ever known about go-to-market. It changes every three months – maybe every month, maybe every 20 days. Things are moving that rapidly. Bring in someone who's been in the foxhole, has the bruises and scars to prove it, but who will iterate. Not someone pulling out their old playbook from Oracle 10 years ago saying, "This is what worked back then." That doesn't fly anymore.
(25:02) Dale's Most Expensive Mistake
Adam: All right, I want you to get a little vulnerable. What's the most expensive mistake you've personally made inside a client's business? And don't give me a sanitized lesson – I want a mistake that actually cost someone cold, hard cash.
Dale: So this was actually before I was in sales. I was working at a company and we had a go-live that had to be done. I was writing some SQL code in their production database – it was about 2:00 in the morning. And I ran a delete command. Deleted some tables in prod. I almost had a heart attack.
Dale: I'm thinking, "What do I do?" Thank God we had a great architect and a backup in place. But as I hit that enter key, I knew immediately – "That is not going to be good." And then I watched all the deletes happen on the screen. It cost us another five hours of work, we had to tell someone, and they lost a bunch of orders. We're talking in the hundreds of thousands of dollars. And this was about 20 years ago.
Adam: Were you fired?
Dale: No. Because I owned up to it.
(26:35) Why Great Leaders Pause Before Reacting
Adam: You and I are very different on camera. I'm the laid-back hoodie guy on a normal day – loud, energetic, wanting to lead the room. You can absolutely lead a room, but you're more reserved, more calm, more measured. How different are you when a client is actually bleeding? What version of you shows up?
Dale: Interesting question. I need to get an action plan together as fast as possible. But I've learned over the years that freaking out doesn't work. You need to keep a calm head because if you don't, the decisions you make in that moment will be worse in the long run.
Adam: Would you say I don't keep a calm head?
Dale: I think it depends on the situation. You tend to respond immediately, which is both your biggest strength and your biggest weakness. Problem arises – great, here's what we're going to do. And to your point, maybe it's right, maybe it's not. Whereas I'm usually the one messaging you on the side while the customer is still talking, saying, "Do not answer yet." And you're right nine times out of ten for doing it.
Dale: Snap decisions get you in trouble most of the time. If you don't take a beat and ask, "What's the real question here?" you end up solving the wrong problem. Same thing with the forecast question we discussed earlier – before I give you a number, I need to understand why you need it so badly. Because if I understand the why and I can get behind it, we're going to find a way to get there. But if you're asking for something that makes no sense, I've got to tell you that too.
Dale: If something is blowing up, I need to understand the root cause, then develop an action plan, then communicate that back to the customer clearly. Firing back while taking fire – I've learned over 50 years that that's not how I operate most successfully. I need to chew on it, even if it's just for a few minutes.
Adam: You've got to sleep on it. And frankly, I've never had a founder, a CEO, a CFO – anyone we work with – get upset if the answer is, "Hey, I need to really think about this and I'll get back to you tomorrow." Because the alternative is worse.
(28:57) The Danger of Surrounding Yourself With Yes People
Dale: That you can't always do, by the way – sleep on it. Sometimes you can't.
Adam: True. And as much as I tend toward instant reaction, that's where we should be living – do I truly understand the problem, or am I just giving you an answer that placates you?
Adam: This is where founders and CEOs get into trouble. If you have a bunch of yes people around you – and we've worked with some of these – you are destroying your company.
Dale: You will go to zero faster. If no one can make a decision besides you, you're going to zero. That's my prediction.
Adam: Couldn't agree more. And that's a wrap for this episode of GTM Uncensored. Founders, CEOs, revenue leaders – if you're accountable to a real number, this is the show for you. Hit subscribe. New episode every Wednesday. Newsletter drops every Sunday.
GTM Uncensored — Dale Zwizinski
Clean Transcript
— Opening: The CRO Scenario
Adam: All right, dude, here's the question. You are just hired, you're the CRO. It's a $25 million company. You uncover that there's three years of shit CRM data. You have the board down your throat saying, we got to have a forecast in a week. We have our quarterly board meeting, got to have a forecast, and it's got to be right because your job depends on it. Where the hell do you start, dude? Because I know you've been there.
Dale: I think there's two things. One is I need to really figure out from the CEO or the founder, whoever it is, what number they actually presented to the board and how they presented it and what those caveats would be. And then what I would do is I would look through the data to get a level set on where we stand today. And then I would say to the CEO, we would have to build out a plan together to say, I know you presented this to the board. This is not really what we need to do. We probably need to recast this number. And then what I would do is probably use some kind of AI technology like Claude to go through the CRM, find out where some of the real data is. And while I could give a draft pipeline and number, I would put it with a caveat — I've only been here for a week. We need to figure out exactly what that number is. We probably haven't done a bottoms-up model. What is the actual number? And trying to find out from the board why that number is so important to them. So have that conversation with the CEO — there must be some reason why we've given this unrealistic number to the sales organization. Once having that conversation with the CEO, I would actually put the board on notice a little bit and say, why did you guys —
Adam: Whoa, whoa, whoa, whoa. Let me get this straight. You're there for a week and you're going to put the board on notice.
Dale: There's a reason why they hired me as a CRO because they know that's broken.
Adam: Yeah, I don't know what that —
Dale: Reason is, but yes. And they know that what they're doing is not realistic. So we all need to get on the same page. If I just take their number and say, okay, that's realistic — I have no clue or understanding of whether it's really realistic. So what I would do is I wouldn't push on them —
Adam: That though, because every board — you've been there, I've been there. This is the number. We have to hit this to get that. And you talk about a lot — you don't want to be the first, you don't want to be the second. Arguably you want to be the third, but I think this is part of why. So I like where you're going, where it's that they hired you for a reason, but how do you push back without making your 18-month tenure 18 days?
Dale: Well, I think you just got to understand the why. Why are we doing this? And then if that number is really that important to them and they've cast it to somebody else or they need to sell the company within 24 months, there's a reason why we have this number. And if they can't come up with a good reason, that's a telling sign.
Adam: Why didn't you come up with the reason in your interview process?
Dale: Probably because I didn't have enough data points. You need to get through the data. It could be like, fine, you want that number. Well, we have to go hire four more enterprise reps and we have to ramp them and we have to go through an entire process with them. There's reasons why they want the number. And I've done this with many boards as well. We just go in and we have a conversation and I say, look, we will get as close as we can to the number, but here's the realistic number. Here's the pipeline, here's the analysis and capacity. You're coming down from a top-down perspective. Let me give you a bottoms-up perspective and let's come to a middle ground.
Adam: Why are they so afraid of bottoms-up though? Other than the fact that it makes their whole model go to shit because they realize that they can't achieve what they want with the people that they have.
Dale: Yeah, I don't think they're afraid of it. I think they don't understand it. I think they haven't truly digested it. It's just the way they've always done work. So it's like, let's just do a number. We need to grow 20%. So put 20% on top of the number and that's the number, without making any differences. So there's broken things. It could be ideal customer profiles, could be buying personas. All these things need to be evaluated because you brought me in for a reason. What was happening wasn't working. So why are we just going to take what's not working? It's called insanity — trying to do the same thing over and over again and expecting a different result. I think we would have that conversation whether they would like it or not. I would think I would have enough clout with the board on the first meeting after a week to be like, this is where we're going. And I wouldn't take the job, by the way, if the CEO didn't have my back. If the CEO didn't have my back and was like, I trust in you and I believe in you — why am I there?
— Coding Background and the GTM Mindset
Adam: Agree. All right, let's shift gears. One of the things I love about you most is one of the things I hate about you most, and it is your background in coding. Prior to entering the sales world, prior to entering the SE world — little fun fact that most people don't know — you actually coded, you developed. And I think I'm grateful for it because of all the stuff we're building out with everything that's happening in AI, but I think it makes you much more analytical. One of the things that you've really taught me is the answer of, I need to sleep on it. I need to think about it. And I think that's very much the coder in you. But what did coding teach you about go-to-market that most go-to-market leaders — even myself — will just likely never learn?
Dale: I think it's understanding that you need to build the proper spec and the information you want to actually deliver. So there's a plan that you need to build out — in that plan, a series of steps. Underneath those series of steps are really tactical things that you have to do. And I think a lot of people just go into, I want more top of funnel. It's like, great, you want more top of funnel, but to get more top of funnel — and that's a great example — go hire more SDRs. That's their mindset. Okay, but to go get more SDRs, now you've got to think: do I have the right job description? Do I have the right onboarding process? Do they understand what the value proposition is? There's a lot of other things than just hiring new people. So it's like that domino effect is what you need to do. I remember the first time I was coding and I was in a lab and I was typing it out and "hello world" came up on the screen. I'm like, that is the coolest thing. And I feel that same excitement now with AI. In the AI world, you as a business person actually have way more control over what you really mean because you get instant feedback. In the development space, or even in the go-to-market space — let's talk about that for a second. If you're like, we should change up our value proposition, and so you start changing your value proposition, then you're changing your email content and your outreach and you're going to change your website — you don't get feedback for three months. And people don't want to wait 90 days to get feedback. They want feedback in 90 seconds. And so that's what the new AI world gives business people — the ability to have that instant feedback to understand, oh, I know I said that, but I didn't mean that. So coding is very black and white — ones and zeros. Everything else becomes shades of gray, and we need to get away from shades of gray and get very specific on how we're doing things. It's not like the ones and zeros, but it's also not these shades of gray where you just say, I want more top of funnel. You have to get very specific on the goals you're trying to accomplish. I find that people don't set goals very well. It's like, what do you want to accomplish? And we do this all the time in our go-to-market sprints — what are we accomplishing in the next 30 days? How many times did we set a goal in a sprint at the beginning of the month and at the end of the month we are in a completely different world? We're deviating, we're going to other places, you find different problems. But in those different problems, you have to identify the root cause, because if you don't get to the root cause, you're solving for something that won't solve your problem.
— Data, RevOps, and Making Information Digestible
Adam: Let's talk a little bit about root cause and data and solving the problems. So we have so much data at our fingertips — more than we've ever had. You have your CRM data, your RevOps data, your AI tools data. What are people getting fundamentally wrong about how the data should actually work, that allows you to make the decisions you really need to make that are going to drive the business forward?
Dale: Yeah, that's a really interesting question because we always wanted more data. The problem is the data's not digestible. And we don't really believe in the data all the time. And so until you get trust in the data — just like you would have trust in a person — you need to have trust in the data. Then what you need to do is be able to get it to a place that's digestible. So the way we're going to present data to the board is completely different than the way I'm going to present it to my team. It's completely different than how I'm going to present it to the marketing group because everyone just has a different way. So it could be the same data, but you have to make it digestible for the organizations that you're building it for.
Adam: How do you do that though? How does a go-to-market leader who is not a data expert — and maybe that's the problem, that they're not the data expert — how does that go-to-market leader make the data digestible? Do you need an AI tool?
Dale: I think, depending on where you are in your cycle of revenue, you really need a RevOps person that can find where all this data is. The problem isn't the data. The problem is: are you getting the right data in the right place that can be put into a world where you can digest it as a revenue leader, to then articulate it out to the board, to the team, to your colleagues and peers? And so if you're getting to five million in ARR and you don't have a RevOps person, you're failing. The first five million, it doesn't really matter. You're trying to get revenue, you're trying to get top of funnel, you probably have the wrong ICP.
Adam: Throw shit against the wall, see what sticks.
Dale: Exactly. So you're just doing that. But once you hit five million, now you should be having your systems in place, you should have your data in place. There should be layers of things that you're building the foundation on. Because prior to that, if we go back to the go-to-market gap, it's complete chaos. And so you've got to stabilize it and then you've got to build the foundations. And in that foundation building is the world of revenue operations. If I'm running a company, $5 million is the right place to consider it — four, five million — because now you've got to build the structure and the foundational pieces.
— What a Broken Revenue Org Feels Like
Adam: What does a broken revenue org actually feel like from the inside? So you've been there, I've been there. We have worked at companies that we got sold to like we're investors. We walk in and we're like, "Holy fuck, we got a problem." What's going through your head — other than, this job?
Dale: I think if the CEO understands that and is okay with all of the modifications and changes that need to happen, I think it's a level-set conversation — okay, we talked about this during the interview process, but here's the reality of what's happening. And it happens to us as well. We come in there, we've been told, "Oh, there's tons of pipeline. There's tons of opportunity." And then we go do a pipeline analysis and it's like, okay, no one's touched that deal in six months. You talk to the rep and the rep's like, "That's not happening." And it's like, why is it in the pipeline? So you go through that entire piece and there's so much tension.
Adam: What about companies who count revenue from customers that have churned — but churned mid-contract — and we're still counting their ARR?
Dale: And especially when they're three months out. Seen that happen. There's some interesting stuff that people are doing. But back to the question of what it feels like inside the organization — it feels sticky. It feels like you're in mud, you can't make any movements. And it feels like everyone's got a political landmine that they're laying for you. And it's very hard to make any trajectory or movement. If you're in that and marketing isn't aligned to you, or marketing has a different revenue goal or perspective than you do — that is a completely different problem. And then you're battling with them and then you're battling potentially with the CEO and everyone's trying to get everyone fired. It's toxic.
Adam: That's it. I think in every broken revenue org I've been in — chaos, silos, infighting. Everyone's out for themselves. No one has each other's back. I have worked with marketing leaders where regardless of whose fault it is, it's: we collectively messed up and we collectively need to fix it. It's a go-to-market unit. In these broken orgs, it's: this is a lead problem, my sales team is doing everything they need to do. But when these orgs are broken, I find we're seeing certain stages of the customer journey being underestimated — where it's typically breaking at certain areas. Where do you see that most, and are you able to attribute a cost to that?
Dale: I think the biggest cost, especially if we're talking about revenue orgs five million and above, is really fixing the customer success side of the world. Because your customer acquisition cost is so high in a lot of these places — it's hard to get people in the door — that if you are trying to patch the boat from the backside, that will just cost you time, money, reputation. All of a sudden you become non-relevant. And then the other thing I'm feeling especially right now is this whole world of the SaaS apocalypse that people are talking about — getting away from seat-based pricing and all of these things that are happening on the SaaS side of the world. I heard a podcast the other day that basically said people are buying SaaS companies at one and a half times revenue because they're going to convert them into AI-native applications. And so this whole world of the seat price is going out the door. What is the real cost of not knowing your market, not understanding your ICP, not understanding your GRR? These are all things that people are looking at, and there's sharks in the water that are looking for blood.
— The Sales-to-CS Handoff: From Handoff to Handshake
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Adam: You just touched on CS, and I think I do agree that CS is where I see a lot of broken things, but I think that starts with the sales-to-CS handoff. And I think that's where revenue goes to die in a lot of companies. I think what people are calling a handoff isn't a handoff. How can we fix that? Because I would say consistently, certainly across the majority of companies we've worked with and worked for, that's been a problem. What has to be true on both sides to fix that problem?
Dale: I think the first thing is we've got to get away from this word "handoff" and get to the word "handshake." And in that handshake world, what ends up happening is CS is part of the end of the sales process. So there's overlap that happens — it's not like I have a customer, now I'm handing it off to you. And the customer — this feels bad for the customer as well. Who wants to be handed off?
Adam: Sometimes do I like my sales rep or not?
Dale: Well, and even better — if I didn't like my sales rep, am I not going to like my CS rep? And so if you have the CS person involved, let's call it at the proposal stage. So you're going over a proposal with your client and you're in the sales world and you bring in the CS person — that would be potentially a sign. We have to be careful about some of that. But to listen to the proposal and listen to the questions the customer has and understand the problems that the customer is dealing with — now you start having the handshake. Okay, I was in the meeting, I understand what the proposal's about, I understand the questions that are being asked. And when we close a deal, they've already seen me, they know my name, I can start talking their language — just like we would do at top of the funnel. We try to figure out all the ways we can interact with somebody and understand them and do all the research.
Adam: The top-of-funnel handoff is broken in most orgs too, right? I don't ever want to talk to a BDR, have to go through discovery to get approved, and then talk to an AE. That's the most frustrating experience on the planet.
Dale: Sure, I totally agree with you. So I think that's a whole different world. And I believe actually where that handoff is dying is potentially starting with marketing as well. If we're not bringing in the right leads, or they're not the right value proposition, or we don't have the right impact — we do a lot of spice interactions and training, understanding that impact. And that's the other part of this handshake. The customer success people need to understand what that impact is that we're selling. So if we're selling software at $100,000, what's the impact that they're going to buy it for at that hundred grand?
— CS as a Revenue Function: NRR, GRR, and the Feedback Loop
Adam: So yes — and most customer success people are measured on NPS or renewal rates. I'm a big believer, and I believe you are too, that CS teams are a revenue function. So if we call our CS team a revenue team and we're doing a handshake, what does that scorecard actually look like? What are they measured on that most aren't today?
Dale: I think the biggest ones — there are two of them that they should be measured on. One is NRR, which is the expansion revenue that we're running off the baseline, and GRR, which is the renewal rate. The interesting part about GRR is you can't ever get over 100. NRR, you can get way over 100. We've had clients where NRR is at 150, 160, 170%, which is great. So you have this land-and-expand motion. And now that you know that it's a land-and-expand motion, you can bring that back to sales. Sales can start putting in a motion of, hey, we don't need to sell $100,000 widgets. We can sell $10,000 widgets and they'll grow to $100,000. So you have that knowledge. So if they have 150% NRR but their GRR is at 85%, there's a juxtaposition there — we have a lot of clients that we're expanding, but we have a lot of clients that we're losing as well. So we're not renewing them. And that could be a bunch of different things — could be the product isn't what we described it as, it could be it wasn't the right ICP, sales oversold, customer success isn't doing their job. There are so many different interactions in that go-to-market strategy all the way from marketing to CS. You have to weave that strategy all the way across — there's got to be a common thread across that whole line. If we're losing people or we're not renewing them, that information needs to go back to the product team, back to the marketing team, back to the sales team. And I don't think that loop is being closed at all.
— The Monday Morning Move: Auditing Your CS Team
Adam: I think there's a fundamental CS problem, and that takes me to this week's Triple M — the Monday Morning Move — which is fairly simple in my mind. Tell me if you agree or disagree. You're unsure about what your CS team is doing and what they're measured on. Look at their calendar. Count how many hours are admin, how many hours are notes, how many hours are check-ins, CRM updates, QBR prep. If it's more than 50%, I don't think you have a CS team. You have a scheduling team, and it's time to fix the systems, the processes, and more importantly, the job description of what the CS team does. Agree or disagree?
Dale: Yes, I 100% agree. And I would add one little other thing. I'm a big believer in having an initial meeting at the beginning of the week and a quick wrap-up meeting at the end of the week. So setting up your week on Monday — having a quick conversation or a Slack message or whatever — and just have them outline quickly who they worked with, what client they worked on, what challenges they potentially have, how I can help them make it better. So you can actually get the information from them without having to look at their calendar. You can just be like, "What are the things you're working on?" And you go, "Well, it feels like 20 hours worth of work. What happened to those 20 hours of work?" And then they start rattling off all this other stuff. And if that becomes the way they are doing their work, either we have a broken process or we have a broken individual. We have to fix whatever the problems are.
— Telling a Founder What They Don't Want to Hear
Adam: All right, I want to get a little spicy. I want you to tell me — and not a story you've told me before — tell me about a very specific time where you had to tell a founder something they really didn't want to hear. What was it, and more importantly, what happened?
Dale: Yeah, actually it was before I was getting hired, and I basically told this founder: you can't afford what you're trying to get into. They only had a couple of million dollars in revenue. And I told the person, "You should have a fractional leader in this space. I don't want to come on full-time. It doesn't make a lot of sense. This isn't going to work out well."
Adam: Is this the company that hired me full-time?
Dale: No, no, no. It was a couple before that. And I said to the founder, "You have a great product, all this stuff, but let's get some of the pieces set up properly. Then let's go through it." So — no, my board wants full-time. I heard the story and I'm like, okay. So I ended up going in full-time, but the same story — three months later, the pipeline's not there. We're starting to build, and I'm putting in all the foundational pieces, but the writing was on the wall. They didn't have enough runway to write the check.
Adam: You still took the job.
Dale: Yeah, but because I believed in the product. And when I was talking to the CEO, it's like, I have this product, I have this prospect, I have this prospect. And we went through their CRM, I started going through the data. I was like, okay, you have it. But then when I went and talked to the sales rep later on, nothing's happening. They can't get back to the person.
Adam: Lessons learned on questions to ask in interviews.
Dale: Yeah, 100%.
Adam: I fell for a product that was a big giant Figma demo, which is a whole separate conversation.
Dale: It was a great Figma demo though.
Adam: It was an amazing Figma demo. That is a whole other story. We could do a whole episode on that alone.
— Revenue Reimagined: What's Fundamentally Broken
Adam: All right, let's get into our uncensored questions. Revenue Reimagined is literally the company name. So talk to me about what's broken about the way revenue actually needs to be reimagined. What are most companies that you see just doing fundamentally wrong?
Dale: I'm going to always go back to foundational, foundational, foundational. You've got to build the foundational pieces because we're building things on top of shaky foundations and they're wondering why things are not working.
Adam: Like my full inspection that just failed. True story, y'all.
Dale: Exactly. You need to have it laid out. And I'm not saying go into analysis paralysis. You have to have quick iteration. The problem is people think they're solving a problem and they put it on a shelf. It's like you're solving a problem, then you reiterate. You're solving a problem, then you iterate. You've got to keep doing it very quickly. So that's the first thing. And then I think the second thing is just tear down all the silos. Forget about everything you've ever known about go-to-market. It changes every three months, maybe every month, maybe every 20 days. Things are changing so rapidly. Forget everything you know. Bring in someone that's been in the foxhole and has the bruises and the scars to get it done. Someone that's not going to pull out their old playbook like, "Oh, I ran that when I was at Oracle 10 years ago and this was what worked." And it's like — bullshit.
Adam: You did work for Oracle, didn't you?
Dale: That's why I don't bring out that playbook.
— The Most Expensive Mistake
Adam: All right, I want you to be a little vulnerable, Dale. What's the most expensive mistake that you've personally made inside a client's business? Don't give me some bullshit lesson. I want a mistake that actually cost someone cold, hard cash.
Dale: So this is actually before sales. I was working at a company and we had a go-live that had to be done. So I was writing some SQL code and I was in their production — it was like two o'clock in the morning. I was in their production database and I did a delete on their database and deleted some of their tables in prod and almost shot myself. I was like, "What do I do?" Thank God I had a really good architect. We had a backup. But on that motion it was like — I was going to hit the enter key and as I hit it, I'm like, "Oh, that's not going to be good." And then I saw all the deletes happening on screen.
Adam: Can you attribute a cost other than time, effort, and a lot of heartache? And did you tell someone?
Dale: Yeah, it took us another five hours. We had to tell somebody because they were selling PCs at the time. So I think they lost a bunch of orders. It was in the hundreds of thousands — but that was like 20 years ago.
Adam: Did you get fired?
Dale: No. No, because I owned up to it.
Adam: Have you ever been fired?
Dale: Yep. Yep.
Adam: Another story for another time.
— Leadership Under Pressure: Staying Calm When a Client Is Bleeding
Adam: All right, dude, you and I are totally different on camera. We have very different personalities. I'm the laid-back hoodie guy, the loud, energetic, want-me-leading-a-room sales guy. And you certainly can lead a room better than most people that I know. But you are definitely more reserved, more calm, more measured. How different would you say you are when a client is actually bleeding? How different are we, and what version of you shows up?
Dale: Interesting question. I think I need to get an action plan together as soon as possible, but I've learned — because I'm older — that just freaking the fuck out doesn't work. You need to keep a calm head because if you don't, the things that you make decisions on in that moment will be worse in the long run.
Adam: I'll say it — it's my biggest strength and my biggest weakness. I tend to respond immediately. It's my Achilles heel. It's like: problem, great, this is what we're going to do to fix it. And to your point, maybe it's right, maybe it's not. Whereas you're the first one who will message me on the side as the customer's telling us the problem saying, "Do not answer." And you're right nine times —
Dale: Out of ten. I think snap decisions most of the time get you in trouble. If you don't take a beat to be like, "What's the real question?" It comes back to one of the questions you asked earlier — how do you handle a certain situation? The whole revenue thing — I'm going to give you a forecast, but why? Why do you need this forecast so bad? Why do you want that number? Because if I understand the why and I can get on board with it, we're going to do it. But if you tell me something that makes no sense and I can't do it, I've got to tell you that as well. So if something's blowing up, I've got to understand what the root cause is of the problem. Then I need to figure out what the action plan is for that problem, and then I'm articulating that back to the customer. But if I'm getting fire coming in and I'm firing back, I just have learned over my 50 years that isn't the way I am most successful. I do have to chew on it, even if it's a few minutes.
Adam: You've got to sleep on it.
Dale: That you can't always do, by the way.
Adam: Can't always sleep on it. I will say — as much as I tend to be more instant reaction — I've never had a founder, a CEO, a CFO, anyone we work with give us shit if the answer is, "Hey, I need to really think about this and we'll get back to you tomorrow."
Dale: Because that is where we should be living — do I truly understand a problem, or am I giving you an answer that is placating you? This is where founders and CEOs and all these people, if they have a bunch of yes people around them — and we've worked with some of these CEOs — you are destroying your company. You will go to zero faster. If no one can make a decision besides you, you're going to zero.
— Closing
Adam: I couldn't agree more. That's a wrap for this episode of GTM Uncensored. Founders, CEOs, revenue leaders — if you are accountable to a real number, this is the show for you. Hit the subscribe button. New episode every week on Wednesday, newsletters drop every Sunday.