2025 GTM Mistakes & What Not To Take Into 2026 (Year-End Recap) with Dale Zwizinski

This year-end recap episode, "2025 GTM Mistakes & What Not To Take Into 2026," features Dale Zwizinski discussing critical insights for B2B revenue professionals. The hosts reflect on the widespread disappointment around AI's initial overhype, emphasizing that effective AI implementation requires human involvement, clear objectives, and well-defined systems, moving beyond simple prompt engineering to a skill-based approach. The discussion also tackles persistent GTM failures like the continued reliance on "spam cannons" and the perils of chasing a broad Total Addressable Market (TAM) instead of niching down. Significant organizational design flaws were exposed in 2025, particularly in customer success (often treated as an afterthought) and RevOps (misunderstood as mere SalesOps). The episode highlights the reality of pipeline panic and advocates for a return to fundamental sales practices: genuine discovery, problem-led messaging, and even picking up the phone. Looking to 2026, the experts predict exponential growth and power shifts towards post-sale functions like Customer Success, along with significant tool consolidation. Leadership success will increasingly depend on deep AI expertise—understanding LLMs and their process integration—rather than just superficial prompt engineering. The episode underscores the need for systematic approaches and a proactive, data-driven investment in GTM functions to ensure sustainable revenue growth.

Discussed in this episode

• AI hype in 2025 led to widespread disappointment as companies realized it wasn't a magic fix without human involvement and clear objectives.
• Implementing AI effectively requires careful planning, explicit charters, and breaking down tasks into specific "skills" rather than just deploying "agents."
• The power of specific prompting is crucial for leveraging AI effectively, as "garbage in is garbage out" applies directly to AI outputs.
• The continued prevalence of "spam cannons" and generic mass emailing in sales is a major mistake that gives sales and marketing a bad name.
• Niching down to a Serviceable Addressable Market (SOM) is more effective for revenue growth than chasing a broad Total Addressable Market (TAM).
• Org design failures in 2025, particularly in Customer Success and RevOps, exposed companies to high churn and inefficient operations.
• Pipeline panic is rampant, often stemming from unrealistic targets not supported by actual close rates or sufficient investment in pipeline generation.
• A return to fundamentals like genuinely curious discovery, problem-led messaging, and even picking up the phone are proven methods for driving revenue.

Episode highlights

1. 0:00 — Introduction to 2025's GTM recap
2. 1:05 — AI hype and disappointment in 2025
3. 3:50 — The power of specific prompting with AI
4. 5:30 — Why 'spam cannons' still plague GTM
5. 8:20 — Overused phrases: 'AI SDR' and 'one-click dev'
6. 10:30 — Org design failures in CS and RevOps
7. 13:50 — Understanding and solving pipeline panic
8. 15:30 — Micro-meetings and phone calls reactivate pipeline
9. 17:10 — Return to fundamentals: discovery and problem-led
10. 20:10 — Leadership traits for 2026: AI expertise crucial

Key takeaways

• AI needs human involvement and clear objectives.
• Stop the 'spam cannons' and personalize outreach.
• Invest in true customer success and RevOps.
• Understand your real pipeline conversion metrics.
• Good discovery and problem-led messaging still win.

Transcript

AI is going to fix everything, right? Like we've seen it in every AI company, like just pop in our AI and it's going to fix it. But if you don't have the right human in the loop, the right systems, hell, if you don't know what you're trying to fix, Everyone jumping on the AI bandwagon and then realizing like, it's not what it's all cracked up to be, like it's so much marketing hype. My biggest surprise of the year is that we are still encouraging spam cannons.

Um, I don't understand how it's December of 25, we're going into 26 and I'm still seeing, well, sign up for insert tool here. Um, personalize it a little bit with insert tool here and send out, you know, 5,000 emails a day. It blows my mind that this is still the way we're going. Welcome to the final episode of the year of the Bridge the Gap podcast powered by Revenue Reimagined.

You only get, you only have to suffer, you only have to deal with Dale who can't keep his shit on his desk and me for this last episode. This is our annual year end recap. It is probably the episode I look forward to most every year. We're going to talk a little bit about what is going on in the trenches, what broke, what worked, what's next.

We're not going to talk about how everything should be AI, although I'm sure Dale will talk a lot about AI. Last night, my 14-year-old told me I was AI. We can dig into that a little bit and what that means. He then told me I was a bot.

Um, that was a little frustrating. Um, but let's talk about all things 2025 as we roll into 26. Uh, I'm thrilled, thrilled to have Dale with me here today. Yes, I look forward to this It's all you got is a laugh.

I I like I like getting into this episode every, uh, every year because it's kind of funny to to look at look back and recap what's happening and then what we're going to be doing into 2026, so let's rock it. All right, so we are not going to do a LinkedIn style highlights reel. Like, that's not our style. We're going to unpack what broke, a little bit of what surprised us, and what GTM operators need to carry and more importantly, leave going into 2026.

So, Dale, I got the first question for you. I'm curious. What's been your biggest surprise of 2025? Um, everyone jumping on the AI bandwagon and then realizing like, it's not what it's all cracked up to be.

Like, it's so much marketing hype. And and seeing people like retract and recoil like, oh, now nothing works in AI. And it's like, it's it's just like a reverse of everything that they've been trying to do and figuring it out properly. So, the I guess it shouldn't have been a big surprise that everything was going to be this big marketing hype and then it was going to just crash.

But that's kind of where Yeah. AI is going to fix everything, right? Like we've seen it in every AI company. Like, just pop in our AI and it's going to fix it.

But if you don't have the right human in the loop, the right systems, hell, if you don't know what you're trying to fix with AI, with a very specific outcome, how are you going to fix it? You've done a lot of work with this this year. What guard rails are you putting in place for our clients so they don't get stuck with, um, what I'll call AI shelfware? Yeah, I think it's more about the testing and using AI allowed for prototyping to show like what is possible.

And then the guard rails would really be figuring out how to deploy this if they want to deploy this part of it. I think the the other part of the guard rails is looking at AI charters across the organization. So, people have just said let's jump into AI and like go build this thing. But really, you back to what you would normally do with any other process, go-to-market strategy, execution path, you have to map it out.

You have to like take the time. You have to look at all the individual components and pieces, and then you figure out what parts can actually be built out in AI. I was I was just watching a video that I thought was really interesting about people talking about everything was like AI agents, and we're trying to deploy these AI agents. This, Yeah, you're deploying an ad workload.

Well, this group was talking about actually breaking it down to skills. So, what are AI what skills can you deploy for said agent? So, a agent has multiple skills, just like a person has multiple skills. And so, how do you break the skills down of an individual?

We've done a lot of work with that with our groups this year on jobs to be done. And I think this is one of the things that people don't do because they think they know everything that's to be done for a BDR or to be done for an AE. But I know you've done a lot of work with jobs to be done in nine boxing. So, what what have you learned from that whole experience of building out jobs we done in nine boxing?

Besides, it takes a lot of time and effort. Um, it takes a lot of time and effort, yes, but shit in is shit out. Um, I will tell you the first time I tried to build it and we leverage leverage AI, um, for almost everything. I would say we're a very AI, um, forward company.

But garbage in is garbage out. Like creating a prompt that says, okay, I have these six roles and create a nine-box for me and tell me who needs to do what job, um, isn't an effective way to do it. I think the biggest thing that I learned over 25 is the power of the prompt. Um, you have to be very specific.

You have to give context. You have to give specific instructions for outputs. Um, I am, listen, I'm by no means an Excel wizard, right? Like, I'm decent, but I can now utilize AI to get really complex Excel spreadsheets, comp calculators, et cetera, because I know how to prompt it to get what I want and be very specific.

It's the same with jobs to be done in nine-boxing. You got to put in the good data to get out the good data. Yeah, and then and then actually educating and training the clients that how to actually utilize the data or get the right data in the the system. Like, I I know you did a lot of work with some clients on like just articulating what are these jobs to be done and how do you have to do them, and how everyone's overlapping and stepping on each other, which is actually, uh, taking out the the revenue growth that they're looking for.

So, how do we into 2026, almost simplify things to then accelerate our growth. Yeah, I mean, we're going way off tangent, but I think the the easiest way to explain that is everything has to be systematized, right? And I don't think it's a something that we've done a great job at. You know, you'll build something, I'll build something, Jake'll build something, um, there's some overlap.

It lives in some folder somewhere and like we might all build in different ways. I think to really, whether it's our our growth or client growth, I think to really accelerate in 2026, you have to have the system first. Um, and and that starts with the AI charter. If you don't have the system first, you are all going to run around like chickens without your head and nothing is going to stitch together.

Yeah. Yeah. So, I'm going to keep us back on track. We're going to come back to AI.

Um, my biggest surprise of the year is that we are still encouraging spam cannons. Um, I don't understand how it's December of 25, we're going into 26, and I'm still seeing, well, sign up for insert tool here, um, personalize it a little bit with insert tool here and send out, you know, 5,000 emails a day. It blows my mind that this is still the way we're going. It's funny, as you were just talking through that, what went through my head was Mad Libs, and it was like, as you're talking, insert here, as you're talking, insert here.

Insert here. Yeah. And you know, this has been just not only firing off spam cannons, but this is the way Go-to-Market has been running for a long period of time. It's like, the same thing with just different like, covers on it or different like, uh, articulations of it.

And I do think it's giving sales and marketing a really bad name, because people just want the easy button. And so, how do we become into a place of niching down? Um, I know some of the clients we've been talking to this year, because investors always talk about TAM and total addressable market. And then it's like, well, just go like fire messages off, and you got to do 100 calls a day, and you got to do 300 calls a email.

Everyone. And so, I know one of the things that we've been doing with our clients this year is, um, narrowing down into the SAM, the sellable addressable market, and the SOM, the serviceable addressable market. And we we're just onboarding a client, uh, earlier this month. Are you are you going to sing your are you going to sing your TAM SAM SOM song, Dale?

No, I didn't even know there was one, so that must be one that you sing. I mean, you made it up. You you sang it on the last meeting. Um, so, you know, and I think what was eye-opening to me in that conversation with one of the founders is they did they understood TAM because they're doing a lot of investment, but they didn't truly understand SAM or SOM.

And so, niching down is the new way to drive X, uh, amount of revenue. So, I'm curious. What's the most overused phrase or trend that you've seen this year? Oh, um, for me, personally, I'm going to say AI SDR.

Um, I I I think so many people tried it. It has not worked well. It ties into what we were just speaking about. I think it is so overused and you I we've both traveled to San Fran this year.

And I forgot the name of the company, but they have like these very prominent billboards that's like, replace your people, and, you know, go go hire an ASR. I think that shit goes away in 2026. What about you? Um, I think for me is, uh, I think it's the the trend, since you got to phrase the trend is these N8N or make, uh, developers building these huge visualizations in YouTube and being like, here, click here, and I'm going to send it to you, and it's going to make you a million dollars.

All you have to do is click one button and implement it. And I'll send it to you. And then they they get like 1,000 clicks and like all this type of crap. And and then like, you know, it's just it's just a waste of time because you could never implement it into your own organization or system.

Like, you could never inject that stuff. I liken it back to, um, when I used to do coding, I would never want to get someone else's code because to debug someone else's code is a complete nightmare. Like, you don't know their thought process, what they're thinking through. I can't imagine.

So, it's that same process just exponentially like everyone thinks that they're a developer now. Can't imagine. All right, let's let's shift gears a little bit. Let's, uh, let's talk a little bit about, excuse me, org design.

So, we saw a lot of go-to-market orgs this year built on like vibes or like best practices that collapse. Not vibe coding, vibes. There are a lot of successes. Yeah, correct.

Um, so whether it was CROs wearing too many hats, overpromotion without real enablement, RevOps getting caught between strategy and cleanup. Where where have you seen, whether it be with our clients or just in in the broader space that you're talking to? Where have you seen org designs get exposed in 2025? Yeah, um, right now I'm seeing a lot of customer success orgs getting exposed bad, um, because they didn't have an they didn't have a customer success organization or a client success organization, however they describe it.

Yep. And then they're trying to build it with people that they already have in house via like a PM or someone that doesn't understand revenue. And it's just not one organization. I've seen this happen over multiple organizations.

And I think it's a little challenging because you need a good enablement in place. You need a good training program in place. Um, you have to like, it's almost like foundational on, you know, what is revenue? What do we mean by revenue?

And then like, they're you're in the middle of of emotion and now you're trying to build all sorts of other like, pieces around it instead of being like, okay, let's, you know, are they the right people and the right seat at the right time? Back to like the EOS ethos that we talk through. People buy from people. That's why companies who invest in meaningful connections win.

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Yeah, I I don't disagree. Um, I think CX has been thought of as an afterthought. Um, much more reactive than proactive. Um, go talk to the customer, but no real focus on revenue or focus on retention.

Um, and I say this as as you know, someone whose wife leads a CS team. Um, when you have that mindset, what you really have is like clerks, if you will. Um, you know, and you don't have any people that are driving revenue. And CS is absolutely a revenue-producing function.

Um, arguably can be just as big of a revenue-producing function and maybe even more important of a revenue-producing function than new sales. Um, I was talking to a colleague yesterday who told me that they want to leave their organization because the C-suite will not invest in proper CS and everything is so reactive and their churn is like upwards of like 9% for the year. Like, brutal, brutal churn numbers. Um, and I think you are seeing revenue leaders get exposed for not knowing, oh yeah, I've led CS before.

No, you haven't. Um, you you have not led real CS before. Yeah. What other parts of organizations got exposed that you just you keep me jumping on my back and like taking what I was saying.

Rev RevOps. Um, I think too many people for too long have thought RevOps is SalesOps, and you just need a Salesforce admin or a HubSpot admin and like you have a RevOps team. I will tell you in my opinion, RevOps is the single most important commercial function in an organization. Um, you need a strong RevOps person who could tie together sales, marketing, success, finance, um, in the days of going and finding someone who was a BizOps or Salesforce admin person at some big company and now having them lead RevOps, um, is over.

I think companies have died because they don't have the right data. They don't know how to stitch together the data they have. And there's all this infighting about who who owns operations. RevOps should report to the CEO.

That's a hot take. That's a hot take. So, in the motion of Who do you think it should report to? I think CEO as well.

But in the motion of No, I mean, you do use it. In the motion of revenue operations, let's go right to the next segment, which is pipeline panic cycle. Like, every team that we've talked to this year, pipeline wasn't there, or they're not doing conversions, and then they like just the convert like the the board's game jumpy, the executives are getting jumpy. And then they react Jumpy?

Jumpy? What's jumpy? And then they react, and then it's like, okay, then Yeah. Fire everyone.

Then, uh, what happens with the go-to-market motion, it gets kind of like exposed. And now you're like jumping back and forth, jumping back and forth. And it kills the whole momentum. And so, we have the go-to-market gap, which is stabilization, foundation, repeatability, scalability.

What we've seen is actually that that panic and that jitteriness will push you back into foundation. I mean, into scale, uh, into stabilization. Yeah, you got to like. Stabilization.

Now you're like, you're questioning the people you have. You're questioning the processes you have. You're questioning the technology you're using. Like, all of a sudden you're questioning all of this stuff, even though you were starting to to to build momentum on your go-to-market motion.

So, um, what have you seen when it comes to pipeline panic? Um, it's real in every single company we work with, every single company we talk to, every single person we talk to. Um, I was just doing a training this afternoon and I say this a lot. A big, fat, healthy pipeline solves 90% of your problems.

What most people don't realize is they're like, oh, we need 3X pipeline, um, because that's the best practice. And I think where the panic comes in is when you have operators like us come in, and we actually start running some real numbers. We start looking at real close rates from different stages. We start looking at the data, and we're like, no, you don't need 3X pipeline.

You actually need like 6 and a half X pipeline to get to the numbers you want to get. Well, the board told me I have to hit $42 million this year. Well, that's great, but you don't have the pipeline to support it. Well, then let's just hire more sellers.

Well, no, that doesn't solve your problem either. Um, the biggest thing that I've seen in the panic is when people really start looking at the numbers and really start doing the math. They realize they have not invested as much time, effort, energy, and or money in developing the proper pipeline that supports the data of the close rates that you have. Totally agree.

Cannot agree more. Cannot agree more with that. So, when you look at across our client base, what do you think has driven either reactivating or restarting pipeline this year? Top one or two things that have actually made meaningful moves in the new year.

Um, I've seen actually in-person meetings, but micro meetings. So, like having like micro conversations or dinners or like events that our that drive value for the attendees and not just like people just attending them. So, that's one part of them. But I want my free steak.

Yeah. Exactly. Um, but but bringing someone that would bring a tremendous value to them. And then I the second one, um, that I think is a little bit off topic and we always come back to it is like just picking up the phone and calling people.

Like, one of our clients, like, the simplicity of like picking up a phone and dialing and just having some conversations with people and not being afraid that you're not going to get a hold of anybody or you're not going to pick anybody up. Um, I think it's just still underrated. Yeah, I I I think it's underrated in a lot of ways. I think it's underrated certainly for getting pipeline, but I think whether it's customer success, whether it's internally, whether it's a problem, the phone is the most underrated tool.

We have moved this era of email and text message and Slack, like, just pick up the phone and call someone. Um, All right, let's, uh, let's shift gears. The return of fundamentals. 25's been a big year of fundamentals.

Um, the craziest part is the stuff that worked in 25. I don't think any of it is new, man. It it's all the stuff that people have stopped doing. Um, so I'd like to talk about the fundamentals that we've seen fundamentally, see what I did there, um, make a difference in driving numbers for, uh, 2025.

Yeah, I Give me a fundamental that that's come back. Well, I don't know if it's ever left. I think it's just good discovery. Like, having good conversations.

Like, what what we're learning as we educate and enable many sales reps and and sales leaders, by the way, since sales reps, it's, um, it's not only asking the first question, but being super curious on why a particular thing is happening. So, you know, why are you having challenges with your whatever? And what does that cause both business-wise and emotionally? Yes, tell me more.

I know. So, it's it it is the it's the single best question you can ask. And I think in discovery, what we need to do to get back to fundamentals is be genuinely curious, uh, of your customer. Like, we don't get genuinely curious.

We just talk because we feel like we should be talking. Yeah. We're all sales people. We all like to hear our own voice.

What about you? Um, I I think, you know, great discovery is certainly one of them. Problem-led messaging. Um, focusing on the problem that you could solve.

If you are not a painkiller and you're a vitamin, you are not not going to be purchased. You have to show your prospects and your customers that you deeply know them, you understand the problem, and that is what you are leading with. No more like you can't this shit has to stop. I get them every day.

Hi, Adam, I see that you're the CEO at Revenue Reimagined and because of that you must struggle, no. Like, that's garbage. There's so much there are so many signals out there, so many things you could research on LinkedIn. There's so many things you could do to really understand what's going on, um, from a problem perspective that if you're not leading with the problem, you're you're you're just not going to move a deal forward.

Totally agree with that. As we move into 2026, no crystal ball, it's just patterns. Like, we're not going to be Nostradamus here. What are some of the, uh, trends or things to look out for in 2026?

Um, let's start with Go-to-Market org structures. Like, what are you I think CS is going to continue to grow exponentially. Um, and and there's going to be a continue to be a power shift from top of funnel to post-sale. That's that's the way I feel and that's what I'm seeing.

Curious what your thoughts are. Yeah, I I think that's accurate. I think you're going to see tools die. Um, I think you're going to see a lot of cons.

Come on. Name a couple tools. They're going to die. Come on.

Nope, not going to do that. Um, I think you're going to see a good amount of consolidation. Um, I think, you know, areas where we have two, three, four, five tools. Um, those are going to change and you're going to get down to to one or two.

Yeah. I totally agree with that. I I actually think people will the people that are educating themselves on what the AI is, what technologies, how you're going to run it. I think all those things will help us in and going back to basic design mode, will help us.

So, I couldn't agree more. Um, here's a leadership trait that I think will get you hired next year and one that I think will get you fired next year. I think one leadership trait that's going to get you hired next year is having that skill of understanding what LLMs are doing, how to implement them in a process. So, jobs to be done, skills, execution on skills, breaking those apart and figuring out what human should be doing and what machine should be doing and how we blend those together.

I think that is the number one skill that will get you hired. And I think the number one skill that will get you fired is just one prompt engineering. I like that. I I I will go one further.

If you as a leader, if you are not or cannot be an AI expert, you are not going to succeed in 2026. All right, quick rapid quick rapid fire, um, and then we'll wrap it up. What is the one tool you'll bet on for 2026, Dale? Google AI Studio.

Ooh, spicy take. That's not one that comes up a lot. What's the, uh, one tool you'll ditch? Uh, one tool I will ditch.

Ooh, I don't know. I don't have one right now that I would ditch, um, because I think I'm trying a bunch of them. I don't have one at this moment. How about you?

Which what's what's one tool you'll bet on? Tool that I will bet on. Um, and it can't be one that I've mentioned so far that we're we're big fans of. Uh, that's a good one.

Um, I'm still very, very bullish on the native LLMs. Um, I've actually shifted my opinion. I'm all in on Gemini right now. I think Gemini's going to win the race.

Yeah. I I think the Google, so the Google infrastructure is like super spot on. Um, I do think I'm seeing from from Gemini, Google AI Studio, Anti-gravity, which is their IDE platform, and then deploying, uh, deploying from there. So, I I agree with you.

Yeah, and the one that I would ditch is any of these, um, we'll call them sequencers. Um, and we'll just we'll we'll just end it there. On that note, uh, it has been a really exciting 25. I am excited for 2026.

We have some incredible guests lined up for next year starting in January. Some you've heard of, some you haven't, and yes, you will still get to put up with Dale and myself. Have a wonderful, happy. Thank you, everybody.

Have a great year, y'all. Have a great year.