AI-Powered Seller

Why Forecasting Fails — And How AI Fixes It

• Jake Dunlap

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In this episode, Jake is joined by revenue leader Chris Casula for a highly tactical conversation on how AI is transforming pipeline management, forecasting accuracy, and GTM productivity.

Chris shares hard-won insights from managing enterprise and transactional sales teams, and breaks down why forecasting has historically been the “bane of sales” — and why it’s not the reps’ fault.

You’ll also hear real examples of how AI surfaces buying signals, identifies bottlenecks in the sales process, improves win rates, and enables managers to coach more effectively.

In this episode, we cover:
• Why traditional forecasting models fail
• Which AI signals improve top-of-funnel accuracy
• How to identify hidden deal risks with AI
• Why deal reviews are the first workflow leaders should automate
• A new way to think about pipeline coverage
• The mindset shift every sales leader must make in 2025
• What predictable revenue will actually look like by 2026

If you’re a frontline rep, manager, or revenue leader looking to drive predictable revenue and adopt AI the right way, this episode will give you one clear takeaway you can act on today.

SPEAKER_00:

Welcome everyone to another episode. Episode number three one of the AI powered seller. I cannot believe it's been 31 episodes since we started this thing, but super excited for today's conversation. I know you've probably heard me talk about making your forecast bulletproof. If you want, you can go back. I did an episode on how to make your forecast bulletproof months ago. So we'll put a link in the show notes to that for you. But today we're gonna go much deeper. You know, this isn't just about optimizing your current process or adding some other, you know, AI tool. It really is about rethinking the way that your revenue engine works. And today's guest is Chris Casula. Chris, I've known Chris for, I don't know, almost a year. He's a chief revenue officer at Benchmark Analytics. And in my opinion, and I love all my CRO brothers and sisters, uh, he is one of the more operationally minded CROs that I know in the business. Chris has led teams and sales ops at ReliaQuest, a whole bunch of other companies, Lavada, et cetera. And the theme throughout his career has been how do I build repeatable systems? And he is gonna share with us today what I'm so pumped for you all to listen to. Pipeline and forecast accuracy is a pain in the you know what. And what Chris is gonna break us down with is really how do I take care of this? How do I make sure that I can get there, but in a much easier, more efficient way? So you're gonna want to make sure to listen to the end. There's some pearls of wisdom he drops just around for reps and for leaders, what is this gonna look like in the future? And let me tell you, the future is bright. I definitely think it's gonna suck less. So without further ado, Chris, my friend, welcome to the show. I am pumped to have you for our conversation today. AI-powered seller. Chris, looking forward to the conversation. Welcome to the show.

SPEAKER_01:

Yeah, me too. I'm I'm really looking forward to getting in and diving into some of the topics today.

SPEAKER_00:

Yeah, I mean, like, look, and then I think this topic, you know, we've got our audience is, you know, people on the front line, leaders, up to you know, CEOs, private equity. And so I think today's topic around the concept of pipeline management and forecasting, right? Probably the bane. I think it's the bane of like everybody's existence in the revenue org, right? Like, whether you're a frontline rep and it's like, why didn't you forecast? Or you're, you know, you're the VP of sales and you're the CEO and then the board, you know. So let me, you know, you've owned pipeline and forecasting, you know, in leadership at various levels for years. Like, what do you think is the biggest myth, you know, maybe sales leaders have about forecast accuracy?

SPEAKER_01:

I mean, it is the bane of everyone's existence in the go-to-market revenue world. And I would say the biggest myth is that reps can't forecast. You know, I've managed two people.

SPEAKER_00:

I love that.

SPEAKER_01:

Yeah, like it I've managed transactional teams where 80% of our business closes in the same month it was opened. I've managed teams where we're selling enterprise solutions to government. And so, you know, the old joke about government, there's two speeds, right? It's slow and stop. And so forecasting is hard in both of those environments for totally different reasons. The truth is that it's not the reps' fault. Like we've created this world, Jake, where we have systems and processes and incentives that allow things like sandbagging and inflation to exist. And really, we can't blame the reps for inaccurate forecasts because it's what we've trained them and and paid them and structured them to do. The reality is like we can improve our forecasts by improving our processing.

SPEAKER_00:

I think that that's good insight, Chris. Let's get maybe, you know, maybe can we get like some examples here, right? So you think of I'm a rep, my boss is coming to me, or maybe like where does it come from? Like, where did where does the maybe uh this is maybe a better question? Where does it come from where managers like, well, of course a rep should know exactly when this deal is gonna come in, and exactly like that Rachel went on vacation? Like, where do you think that comes from, this kind of expectation that people on the front lines should be you know clairvoyant in some cases? And also, look, I I know that it's part of this is like, well, there's the questions they can ask, blah, blah, blah. But but where do you think this kind of expectation comes from?

SPEAKER_01:

Yeah, it's a it's a really interesting corollary to that, Jake. And I think it's probably two pieces, right? One, as managers, right? We once sold and we thought we had all the answers. By the way, we didn't have all the answers, right? And if you think you did, like you're wrong. The other part is there's a lot of things that happen that we just aren't attuned to. As salespeople, we are really good at things like empathy and building relationships and critical thinking and problem solving. We're not really good at identifying data and combing through information and finding patterns. And so a lot of times those things, which might be signals or indicators, get lost because we just don't know what to look for inside of the broader opportunity. If that makes sense.

SPEAKER_00:

So, where where where do you think they lose it? Like, where do they lose it in terms of, well, now that I'm a leader, I'm expecting this perfection? Like, where does that come from for whether it's frontline or you know, even up to the top?

SPEAKER_01:

Yeah, it's interesting you say kind of up to the top, right? Because that like in a lot of what you're describing is just how sales teams use CRM systems, right? Like, I I'll I'll make a broad statement and I'm pretty sure it's a safe one. All reps hate using CRMs, right? They just hate it. Yes. And they hate it because we've set it up in such a way that this is because my manager told me to. Because someday, right, like our senior leader might look at this and log in and check out my opportunity. And so you end up putting information in there for someone else and not for yourself. That's true. And there's kind of a disconnect in that process, right? I mean, one of the powers of starting to use some of these additional tools and setting up the right processes is that you can start to use the CRM for you as a sales rep, right? You can start to use things like pattern recognition and AI and you know, call it custom GPTs, whatever you want to call it, but that can start to help you identify things like, hey, this particular deal has been sitting in this between these two buying signals for such a long period of time. We're not saying the deal is bad, we're saying we need to dig in on this, right? Like that's where that kind of human element comes in that managers really need to key in on and not on, did you fill out medic? Right, right, because that's not the answer.

SPEAKER_00:

Yeah, that's I think that that's a that's a good call out. Let's talk about the like the CRM piece of that, you know, that you were kind of starting to get into is that like most Rep C CRM is really like busy work and it takes them away from selling. Obviously, this is the AI-powered seller. And I do feel like I think I'll get into some examples of some other automations and things that we're doing that we're gonna enter a much more beautiful era that requires much less of this. You know, how do you how does AI change that relationship between data entry and deal execution?

SPEAKER_01:

Yeah, there's a lot of ways that it can do that, right? I mean, even today, think about things like when I was frontline selling, if you would have told me that we can automatically take our video calls, our virtual calls, and automatically update the CRM with that information. I mean, that like that would have been mind-blowing to me if I was doing those calls. It would have been a total game changer. That's just like the tip of the iceberg, right? So you can get the data into this CRM automatically so you don't have to go in and spend the 30 minutes after every call keying in all of your notes. It also gives you the opportunity to do things, like I said, that salespeople are just generally bad at, right? Can we start to identify things and influencers on deals, signals that say, hey, this deal is actually in a really good place, and we need to do more of this one particular thing, or this deal might not be in a good place, even though it feels good. And so that's kind of that chasm. We're getting good data into our CRM systems, and then through these kind of AI-powered tools, we can get good insights, which will allow us to focus more, and that's really what it comes down to.

SPEAKER_00:

And do you feel like that's the difference between kind of top-performing teams right now or teams that are you know thinking about AI more effectively when it comes to like pipeline management and forecasting? Is that they're like you know, leadership recognizing some of these pains and realizing AI is the answer.

SPEAKER_01:

Yeah, yes, and I would say, right? A lot of times top performing teams they realize that AI, AI is not a silver bullet, right? By the way, that doesn't exist. It is a tool, though, that we can use to get better about forecasting and processes in general. And so when we think about that, like it's wild, right? I mean, we talk about this, Jake. You might not need a manager in a deal review. But that is what we think of as like that's our role as a sales manager.

SPEAKER_00:

I mean, I do that. My thing for 20 years of experience.

SPEAKER_01:

Like, yes, and I've done it this way a hundred times and I've closed a hundred deals. And the reality is those deal, like those deal reviews, you ask the same five to ten questions in every deal review. That is not your secret sauce, right? That is something that can be automated. It's a process-based thing. And if we can do that, if we can bring in a custom GPT to help go through deal reviews, it allows your managers to really focus on the high value things like coaching, high-impact coaching to move deals forward, to develop skills, to build relationships with the sales team and with the customers and prospects. It's a huge difference maker.

SPEAKER_00:

So, what I love about this is again, uh, you're calling out some of the things that many people listening would view as the human parts a little bit. The the feel of a deal, you know, that feel of I can sense Rachel's excited or Tommy's not. Now, the reality about feel is I could have five reps listen to the same call and I'd get five different feelings, you know, in terms of what that looks like. So let's maybe start at like the very beginning. Let's talk about pipeline management. Okay, and we'll kind of start from the beginning, we'll take it through the deal. Where do you feel like, in terms of like top of funnel forecasting, right? Like, where do you feel like AI can help marketing slash BDR sales, you know, more effectively predict, you know, where they're gonna end up?

SPEAKER_01:

Yeah, it's a total facts versus feelings thing, right? And and if you start at the top of the funnel, there's a lot of the, you know, call it force multipliers. That's kind of a cliche buzzword, but it's it's true. It allows you to do more targeted information with people who are more likely to be interested in what you're doing. You can capture signals from all over the place. And and when you start thinking about these things, like what matters versus what the data says matters, it's really fun. Like, and and usually early on in a sales process, you'll get a champion, right? And the champion says, yes, we want to do this, we're gonna do this. And reps get happier because, you know, as salespeople, we want to get to yes. And we're at yes, and this is great. And so what's wrong with that? But it's it goes back to exactly what you're talking about. It feels good, but does that actually have a material impact on where the deal is gonna end up? You can run a lot of analytics and you can probably find out that that raises more questions than answers, right? Can your champion even do this? Can the champion pay for this? Is there a budget allocated? I mean, is it even a real champion, right? And how have you tested that person? And all of those things might lead you to realize that what you thought felt good isn't actually an indicator for success on a deal.

SPEAKER_00:

So if you're somebody who's struggling to continue to use AI in forecasting, my hope is that this episode and all the episodes of AI powered seller, and we've done a bunch, are gonna help you to get better and better about how to leverage AI with your team. Make sure if you are watching on YouTube, you make sure to like the video, share it in your Slack channel with your coworkers, subscribe to the channel. If you're listening, make sure to hit the download button so you always get the latest episodes. I am doing my best to always try to bring you the tactical stuff. And that's what I'm really enjoying, you know, Chris, with this conversation is our ability to really deep dive into what people are doing around this topic and everything AI power related. So if we if we start, if we start with the top of the funnel piece of this, one of the things you mentioned is this more signals, right? And so where AI can help is to better understand real signals. Do you have an example of that? How could a marketing or a BDR or an AE think about the the again being better at focusing their time to spend? You know, like what's a good tactical example?

SPEAKER_01:

Yeah, so uh so many, by the way. One of the things I would use case, especially for this use case, right? Because there's a million prospects out there for even for niche markets, right? Like there's a there's a lot of ways that you can spend your time. And it is so easy to be busy, right? I mean, we can be scheduled 8 a.m. to 8 p.m. and be really busy without actually doing anything. So one of the things we've actually found from a top-of-huner perspective is that focus. The focus is hugely important. And so when we start doing things like uh account prioritization, right, ranking at A's, B's, and C's, or you know, quantifying your ideal customer profile, whatever you want to call it, it's being able to help flesh out some of the more recent insights to the top. So part of what we do today is utilize news stories and positioning of our prospects, things that they've talked about in the public as indicators of whether or not they're going to be good prospects for us. When you think about trying to cover the whole country with your sales team, that's just impossible to do. You'll spend all day reading news and searching Google and doing all of those things. It's not a good use of your time. And so what we're starting to do is say, hey, here's an account that worked really well for us that had something really positive. Go find me 10 other accounts that look just like this. And oh, by the way, once we've found these 10 other accounts that look just like this, help us create some unique messaging that's still on brand with who we are and what we do. And that's right, let's help build that outreach for those 10 specific accounts.

SPEAKER_00:

Yeah, and each company, what I love about this, and it and obviously I I know I know Chris's business also pretty well and the work that they do. So, you know, what this looks like in tactical application is you know, once a week or every couple of days, imagine AI agents that know the trigger signals for your type of product. And I'm not talking about these tools that talk about third-party intent. I really feel like that sector is gonna get smoked personally, of like a marketing person from IBM read a white paper about a topic, as opposed to, hey, we know when a company is hiring this role, we know if this role leaves and changes jobs on LinkedIn, we know if there's a crisis in this thing. Every company, every software, every B2B company, there are those types of triggers that you have. And if you really, really think about, you know, what was the leading factor? It's like, oh, they just started a role. They were a previous user. That to me, Chris, is the power of AI. And to your point, so it says, okay, here are the three people, or five or ten, let's say a big company, let's say you got 10, here are the 15 people that took this type of action. And it says, based on the action they took, here's three follow-up emails for you to send them. That is doable right now, everybody. Doable literally right now. We're actually working with Chris and his company on some of this stuff, like as you know, as we speak. I think that that that the ability to say you don't have to earn your stripes anymore. I think that's part of it, right, Chris? Like it's part of it, is my territory. I got handed 200 accounts and I went through the rain and the snow and the mud and I had to figure out which ones worked out. I feel like that mindset is still, and it could, I think it's subconscious. I don't think any sales leaders out there are revenue saying, like, I want my team to be inefficient, but they know what made them successful. Right. And so we kind of have that tendency to run that play back as opposed to say, you know, hey, now my kid doesn't have to walk to the bus, you know, in the snow with no shoes. I have shoes now. And like uh, you know, and uh maybe a car I can take them in, right? And so I think for a lot of people, it's for the top of the funnel in particular. A lot of this I think starts with a mindset shift that there are new signals that you can track using AI agents that aren't fluffy. It's not like somebody visited a w uh a page about an article and you don't even know who that person is, that are actually really like hyper-personalized to their business. And that that to me is a beautiful thing.

SPEAKER_01:

We still have BDRs. Like that doesn't what you just described, Jake, doesn't take away the business development report. Like we still have them. The difference is instead of going out to say, make a thousand phone calls today, right, and and just scour the web, right? Get the phone book, you can say, hey, here are the people that the message will resonate with. And by the way, it's this message, and go spend your time tailoring and making this relevant and personalized to the specific people who are great opportunities for you.

SPEAKER_00:

Yeah, and and again, think about for all of you, take time and really think about those types of things that happen that usually lead to deals. And if you're not tracking it, you need to start to track it, right? Or have AI help you to understand, or AI can look at the trends, you know, potentially for you. So, okay, so we start to get in the deal now. What do you feel? You know, unless we can even get you know specific, you know, in your last you know, roll that uh, you know, rely quest. Like, what were the biggest gaps between what reps believed about their deals versus what the data actually showed?

SPEAKER_01:

It's it's there's a lot of those, and that's the reality, right? Because we kind of talked about this idea of facts first feelings a little bit already, Jake, where where when I feel like something, when I hear something and I have happy ears, I'm a sales rep, right? Like it's just natural for me to do that. There might be things that are lurking below the surface that we just don't recognize. So at the quest, by the way, this happens everywhere, it's not unique to that, right? Long enterprise sales cycles, really complex things, a lot of data over the course of something like a year, right? And so in those cases, what we found actually is that there was this relatively infrequently used meeting that we had, and it was a specific type of meeting. It was kind of a mini proof of concept thing that we hosted at our headquarters. We found that every time we used that meeting, the deals were closing. And so we said, well, that's a really interesting finding. And it seems obvious in retrospect, but these kinds of things always do, right? But people, especially salespeople, right, of which I am one, we're bad at doing that pattern recognition. And so being able to utilize a tool to help us find those things, it's incredible. And so what we ended up doing is we ended up incorporating proactively incorporating that and suggesting that and pushing for those types of meetings. And we didn't close every deal, right? Like there's no silver bullet. But but it did meaningfully and move the needle for us. And so those types of things, identifying the things that should be obvious but aren't, like that's a huge facts versus feelings thing.

SPEAKER_00:

So, with that, that is a great one. And I love that example. I say this all the time to teams. This is more of sales advice. More meetings many times speeds deals up. And I almost have to fight sales leadership at times with this. That, you know, one of the big reasons why deals might be stalling is you're not having that extra meeting. You're not instead of trying to do it in two, you can do it in three, but you actually drive the momentum faster. You, you know, we then I think that you know that's been pretty revolutionary for a lot of our clients. Of like, you know, if you can actually just add in something that it that's logically makes sense at to get a you know, the right people there, etc., you can have a good, you know, uh increase your likelihood to close. So it sounds like what you're saying is it's really just like taking a look at the sales process and again continuing to orientate toward what produces the the outcome that I'm looking for most consistently and how do we reverse engineer that? And and what could AI catch like for that example? Like what would like let's say in a deal, so big picture we catch that we need this meeting. What are some other signals that AI can catch when reps are in the deal that can help them with you know pipeline forecast accuracy?

SPEAKER_01:

Yeah, I so super specific examples, right? I mean, you might be in a deal and you might say, Oh, well, we've multi threaded into this deal, we've got five contacts at an executive level. AI might say, Hey, look, none of those contacts are in the finance and legal team. And by this stage in deals that you've won, you need to have already engaged your finance and legal team, right? It could be you talk about the the more meetings, Jake. The idea of, oh, we just met with them, you know, ten days ago, twelve days ago. Well, at this stage of your pipeline, you should be meeting with them every three to five days. And that could be a myth that AI can help you recognize. I can do, you know, sentiment analysis of emails where you might again have the happy years of I said, yes, they're still doing it. The reality is they could be doing still evaluating alternatives. And so AI will help you kind of catch some of those really super tactical things that you might feel good about because hey, we just met with them a week and a half ago.

SPEAKER_00:

Yeah, I'm seeing a lot of that. You know, I'm seeing a lot of these tools have an engagement score almost where you know you haven't emailed with them. And I think, you know, who was it? Maybe Clary or something. I think Clary was maybe one of the first tools I saw that was like looking at, you know, okay, how many people were on the meeting invite? Um, you know, how many people are you emailing with the deal and starting to kind of formulate that? But look, and to your point, based on where you're at in the deal, that could be interesting, it might not be interesting as well. And so I think that was kind of a V1 of some of this. And I think what what you're calling out that that most sales AI that the actual rev tech companies aren't doing that Gen AI is doing really well, is all the other stuff. Hey, typically your deals have a CFO. That's John Henderson, because I identified that's John. Right. He hasn't been involved, that's a problem. Or, hey, Jake, you actually did a great job. You just increase your likelihood because you got the CFO involved. Now, let's talk about politics. I just saw that they put a job posting up for this thing, therefore, that equals this. And I think that's where a lot of the RevTech, I feel like today, is just so far behind that it's giving you these signals like, did Jake, you know, did I meet with this person? Yes. Was an email exchange and it seemed positive? Yes. Okay, we've got or like let's go with MedPick. Jake asked who the he found out who the economic buyer was. Jake asked the question. He found out the paper process, right? But it's not understanding the nuances of the deal of like, did Jake actually run a in a good call? Like, was it good?

SPEAKER_01:

Well, and then and then kind of what you're talking about. It's like, yes, you okay, you check this box for MedPick. The reality was the CFO is John. You haven't engaged him yet. Here's who he is, here's how you should reach out to him, here's what might matter because they've just posted this new position. And being able to do that with you know a click of a button or two clicks of a button, like that goes so far beyond what normally would have taken two hours of research, and you're doing it in two clicks.

SPEAKER_00:

Yeah. And so what do you feel like? I think that's a good segue. Companies that are saying, yes, we're trying to use AI for better forecasting, better pipeline management. And so we started to try to use AI. What do you think the teams are doing that get it wrong? You know, especially when it comes to some of the some of the different use cases, whether it's top of funnel, middle funnel, like we're getting into now.

SPEAKER_01:

We've used a lot of tools, right? I mean, we use Query and we so we've got a lot of experience at that in different stages of the funnel. You know, I think one of the things that I see teams that get it wrong, I would say there's two things. They try a shotgun approach, they try to do everything. And we talk about this, Jake, right? Like there's the art of the possible with AI. It can do so much, and it can. However, if you try to boil the ocean, you're not going to get anywhere because there's just too many things. So pick one use case, start with that one use case, get it right, get it good. Like that's I think a key piece. The follow-on to that is if you've got your one use case, you have to make it part of your day-to-day or week-to-week process. And so you mentioned we're working with your team right now. And so part of what we do is every Friday morning, we have a team meeting and we say, How do you use Journey today to make your life easier? And some days I'll be uh, you know, I'll be on with a rep or on with someone and say, Oh, hey, bring this to the Friday meeting because it's a great thing for us to just reinforce and encourage. And then we get to build off of each other's ideas. The more that you like you've got your use case, the more that you use it and actually live it, the better faster you're going to be. And then all of that aren't the possible, you know, can come secondary, right? Like, what's the next thing and the next thing and the next thing, and you build off of it.

SPEAKER_00:

Yeah, so it sounds like, and and trust me, you know, it's interesting. I'll I'll play out some scenarios that we're seeing in real time. You've got the other, well, you most clients I actually would say that we see are still in the complete Wild West. And that means either they know their team's using it, but they still don't have a centralized platform like Journey or something. That's one kind of group. Then the other, you know, they've they've done that, but they really haven't thought through the best practices. It's like we've we've centralized it, etc. And then the ones that, you know, what you're talking about is what we see the people that are really winning are the people that say, look, we're gonna start to create this. And actually, this is something I said to one of our clients yesterday, and I thought that this actually captured maybe the chaos pretty well. This isn't like a your RevOps roadmap, right? Your RevOps roadmap for a lot of companies is like, oh, we need to do this, build a this, and here's my report. You know, you hey, I need a field. Most RevOps roadmaps, and people are like, that's not us, I'm like, that's you, right? Is like give me a requested thing, and I'm gonna go solve that thing. Yeah, compare that to a product roadmap. What a product roadmap does is say, hey, what's the problem the user is having? That's all I need from you. And then I'm gonna translate that problem into the right AI, the kind of combo to solve your problem. And I think that is the gap. I think a lot of revenue leaders, that is what I think they're struggling with when it comes to just picking one or two use cases, is they're like, but yeah, we could use clay tables for this, and then we could we could do custom G. It's like stop. We're gonna build a roadmap and we're gonna do this, and then we're gonna deploy this, and then again, we've got a ticketing thing that fixed the bugs because then ChatGPT releases a new model, and it's like all of a sudden the the prompts stop working as well. So I think for a lot of people out there, you know, listen to what Chris said about how to get it right. Because if you want to get it right, you have to take this more structured approach, and it's okay. Sales leaders, yeah, I give you permission, it's okay to wait two weeks, two weeks to get something that does five things versus a point solution that somebody built and you think that that's good. That would be my like high horse, Chris.

SPEAKER_01:

Yeah, I'm piggyback on it. I won everything yesterday, but it's okay to wait two weeks.

SPEAKER_00:

It is, and and I think the good part is you know, revenue leaders are you know, we're all just kind of learning what AI is possible of, you know, their kids pot can possibly do, but you know, we're all learning this together.

SPEAKER_01:

And so if you if you were yeah, I was gonna say one of the fun things that we did when we started with this, Jake, is we went around uh around a table with with all of our sales team and we said, what are you using AI for today outside of work? And and the the answers were really interesting. People were engaged, people were hungry for it, they just needed a little bit of structure to know how to incorporate it into our sales process.

SPEAKER_00:

All right, Chris has mentioned Journey a couple of times. Journey, my friends, is your your little sales and revenue copilot. It already has all the best agents built out, it already knows your sales force, it knows insights, and instead of your team having to prompt, it already knows how to do deep company research. It's got a little button that says keep deep company research, it says tell me the link and it goes. Outbound meeting co-pilot, give me the link and it goes. Digital SE is one we built for Chris's team. You tell it the problem and it gives you the answer. So if you're looking to get ahead, make sure to check out journeyai, meetjourney.ai for your free trials. And I think that that that's also a good message for my leaders out there. Leaders, it's your job. Like this is we are we are in the middle. Uh I don't have a good name for it. I'll call it the great retraining. But somebody back in '95 had to teach Brenda how to send an email. And someone at the company had to say, let me tell you why we're going to do it this way with the internet versus a phone book. And I think what most leaders still have not recognized, it is our job as leaders to retrain. And I will say for frontline people, it is your own, you got to take responsibility for yourself too, to learn the skills. But it's our responsibility to retrain an entire new way for these people to work. And if you as a leader aren't staying on top of this and starting to think about, okay, let me really understand that. Okay. Let me really understand that. Okay, we should be doing that different. That feels different. And and getting a little bit more hands-on keyboard with some of this, I feel like that that's gonna, if you fast forward two to three years, you know, yeah, probably two or three years from now, I think you're gonna start to see a pretty big gap of sales leaders that had been there and done it and worked at Salesforce and worked at Oracle and were like, you know, making big salaries. And then you've got John, who might not be as experienced, but John just has a completely different skill set and able to scale the way that you know the modern VC or PE is looking for, which is like I'm scaling revenue consistently and I'm not trying to add headcount, I'm trying to add productivity, you know, and efficiency to the GT emotion as a part of this. So if you were a first-time V, you know, if you're a VP of sales and you're listening to this, and I said, I want to get better at uh forecasting accuracy with my team. And yeah, I and I'll limit you. You have to pick one thing. Okay. What's the first thing you would do? Like, what's the one place you would start? And I know, and you can give me your like fast follow second or third, but if you had to pick one, what what do you think it would be?

SPEAKER_01:

You're you're really uh pushing me on just pick one. So look, I think I think just start. We kind of already talked about that, so I'm gonna take a side route and I'll say don't wait for this to be a company and company initiative. Just go do it, right? Start using it. If you wait for it to be a company initiative, Jake, you were just talking about this. Like it's our job to be leaders, to get hands-on keyboard, to be excited about this. You know what? Try something. If it works, great. If it doesn't work, okay. Assess, learn from it, pivot, try it again. Yeah, you're gonna like data quality matters and hygiene matters, which all of that is kind of like the fast follow, second, third. But the reality is if you're not starting, if you're not just going to do it and you wait, you're gonna get passed up exactly the way you were just talking about.

SPEAKER_00:

Yeah, and I think you know, the this moral in that story for me is each of you as leaders and as reps, right? Because I want to be very clear, as you're a rep, you've got to also know your own bottlenecks in the process. Hey, what is stopping me? And guess what? AI is really good at this. You know, you can give AI your last 10 calls and say, hey, why am I consistently not like missing forecast? And it'll say, you didn't do this, you didn't do this, you didn't do this. And you're like, okay, I can now start to do that. And I think the point you're making in just get started is each of you as leaders is probably gonna have a bottleneck in your team that's causing this outcome. It could be uh, you know, the deals that get forecasted. You brought this exit this example up earlier. That when the manager's involved, the manager is able to help the rep kind of round the edges and to say, let's actually forecast it here, let's put it at this stage, etc. But they can't do that for all the deals. The the example you mentioned is what I call 100% deal coverage. That I see a future where now me as a leader, because the reps are self-assessing more, I can actually talk to them about more deals whenever we do talk because they actually come with a point of view. They're using AI to summarize it and say, hey, I think this is what I should do next. And so now I can talk to them about 30% of their pipeline. And then you know, I've got multiple people. So for the other 70%, they're getting my lens on it that would take it through the same rubric that I would, you know, the Chris GPT, right? As a part of this. And and I think that would be a good place for a lot of people to start. Chris was in a room that I was talking to back in July, I think it was, and we were talking to a big group of CROs, there's probably 20, and we were talking about deal review. I very specifically remember this, and there's a few sales leaders in there. Well, you know, deal review, blah, blah, blah. I said, okay, let's whiteboard this. I'm like, what goes into good deal review? And so, you know, we start going, you know, uh, you know, stakeholders ain't da da da da da da da da. And and then I had I was like, okay, what else, what else? So we get this board. There's probably, I don't remember, seven to ten things. Yeah. I say, and I say, guys, all of you said the exact like very similar things. So do you think that if you could program something to do it, what you just said, that it could that it could take care of like a lot of the smaller deals. And I think it was kind of an epiphany for a lot of sales leaders of and and not in a negative way, some of the things we might think are like uber artistic and proprietary. You know, the reality is there's patterns, you know, to your point. There's patterns of of of how this happens and and how you know how you do deal inspection as a leader, how as a rep you do your own deal inspection, and and AI can help you. If you don't know what the pattern is, AI can help you. And so I think that's a good, a good uh start.

SPEAKER_01:

Completely.

SPEAKER_00:

So if so let's, you know, we've got a couple more questions here. Yeah. Forecasting accuracy and pipeline management. Where do you think we need to take it? Right? So if you think it's 2026, you know, you're managing your team, and maybe you can, you know, talk to experience too of how you're thinking about it for your team. What are the things that you you care about? And are there things that you I don't know if it's care about less, but maybe prioritize differently, you know, as you think about the most important part for your team to be successful?

SPEAKER_01:

It's interesting, and I would say the biggest thing that we're trying to think differently about is pipeline coverage, right? Like there's this traditional notion that you've got to have 4x or 5x pipeline coverage, and like quantity is super important and just go get more things in there. Well, it's not about volume, right? It's about visibility and confidence. And if you're doing all the things that we talked about, top of the funnel, identifying the people with the right signals that make good prospects, right? Capturing the right messaging for those people, getting in front of them with the right things, and again, doing it quickly, efficiently with some of these AI-based tools, working it through the process, noticing all the signals that you might be missing along the way, right, with unique touch points. I would rather have two times pipeline coverage for deals that I have visibility into and confidence in that are really strong deals versus something that's like, oh, we've got a 5x, 10x pipeline coverage. Like that's just it's a totally different way to think about it for us.

SPEAKER_00:

I love that. I love that. Yeah, but I mean you have to think of I was really for I when I got my MBA years ago, and I did it because I really didn't learn anything in undergrad. Um, but one of one of the books, you know, there's a logistics course, and there's an amazing book called The Goal. And if anybody is knows, it's a it's a fictional book about logistics. I've probably talked about it before. Uh and you're like, wow, Jake, that sounds riveting. A fictional book about supply, like logistics. And the long and short of it is this there's this like camp troop, and they load up, there's this kid who's not as in shape as everybody else, and he's got the same backpack on as as everybody else, or he's overloaded. And so they can only move as fast as he can move, right? And so what it teaches you about supply, like logistics is the theory of constraints. The whole book is to teach you this concept of the theory of constraint. And and if you think about your pipeline, the sales pipeline is a theory, it is a pipeline that has constraints and drop-off points throughout it. And if you can start to think about what Chris said, which is instead of, you know, hey, I'm just gonna accept the constraints, I'm just gonna accept this is our win rate, this is our win rate from stage one to two, two to three, three to four, right, etc. And or just magically hope and wish that, well, if only the best of the best, you know, the perfect things came in, we would we would get there. And you can you can start to get there as you know, and so instead of saying, hey, we're gonna try to throw, you know, we have to be, I think three X, I feel like, is the one that almost everybody says. It's like, well, where's the data on that? It's like, yeah, 3X. It's just 3X. How long does it take take to ramp a salesperson? Three to six months. It's like, okay, it's like it really depends. It's the answer. Yep. But but the point is, I think for a lot of revenue leaders and sales reps too, I cannot stress this enough. You need to know your own numbers. You know what we do a lot of workships, workshops with folks. I was actually with the the Angels last week in in LA and just talking to the reps about you can't get better as a rep if you don't know your constraints. I don't care what my boss says that the company's sales cycle is, or what my boss says that our close rate is, that doesn't apply to me. My sales cycle is different. And that's the other part I love about AI is we're gonna get personalized on this stuff. Like, you know, to your point, Chris, it's like, okay, Jake needs specs, and if he can instead increase his throughput, you know, take the take it out of Herbie's backpack and give it to somebody else at step three, Jake actually can go down to 2.1 pipeline coverage. And so I think for a lot of leaders out there, you're probably not as far away from this data as you actually think, but I think you do have to start to think about pipeline coverage differently. That pipeline coverage is actually a leading indicator of sales process and effectiveness, right? I mean, I that's how I would think about this, right? Yeah, as some some flavor, some some flavor. I don't know if I've ever articulated it that way, but I think that that feels like directionally right. So, okay, so I've got to look at it that way. What is, you know, when you think about your team and you think about AI applications for this, again, it sounds like obviously pipeline, you know, management, looking at the data, understanding, okay, hey, you know, it's it's this point versus this point, and this is why it's this point, and why is Susan better at it than Ryan? And how do we duplicate Susan or parts of her process? Last question where does this go from here? So we have this new world, and this new world is okay, I've got dynamic numbers, I kind of know my forecast numbers for these different reps. I, you know, I'm using AI to maybe the reps are self-assessing, they're able to do better pipeline and deal management. Where do you think we go from here? You know, most companies aren't here yet, but if you had to predict in 2026, where do you think the next unlock is?

SPEAKER_01:

Yeah, it's you know, there are kind of phases to this, right? And we've kind of gone through these, and by the way, we're not at the end at all. But we see things, you'll see things like the volatility of your forecast will go down, right? You'll see things like more deals, win rates will increase. Ultimately, you want to get to the place where you're, you know, the hero for your CFO and your CEO and your board, where you have accurate forecasts and predictable revenue. That's not that far away. There was the old model where you just added more headcount and you could get there. We're gonna get there in a much more efficient, effective manner where we're growing with predictable revenue and not adding headcount. You're taking your people and you're focusing them on what they're really good at, which is the critical thinking, the problem solving, building those relationships, strengthening deals, and not forcing them to do things like enter data into a CRM and comb through and try to find all the nuggets, because that's also things that we can automate. So I would say the future is getting to a place of predictable revenue efficiently and effectively, and being able to actually forecast accurately. It's it's not as far away as we can.

SPEAKER_00:

I love that. And I'll add that because you started with this and not blame the reps, you know, not say it's there because what we're you know, we can build this system around that's just like it is what it is. It's like this has been taken care of, this has been like we're able to kind of like insulate all the different parts of it to have the AI say, this is the fork, this is what it is. And based on these things, and this is and and I think this is where you know, if you think about the dream of what was supposed to be RevOps, which was this kind of like process optimization org that really isn't that today. That's where I think we get to, though, is you can kind of more quickly identify the bottleneck that's causing forecast inaccuracy. And I think the key for me, Chris, is we can get to the individual level. And I think that is what's always been the difficult part is a lot of most leaders and it's okay if you do this, it's all right. We manage people to the mean. We manage people to the mean of any of the numbers. Why is Jake better here? Ba ba ba. We have and every leader says this. Every leader says I've got to manage to the individual, right? Every leader, no leader disagrees to that. Why don't we manage them to the individual on pipeline and forecast accuracy?

SPEAKER_01:

Yeah.

SPEAKER_00:

Why don't why don't we this is what Jake's thing is, this is what it is. And I think AI, Chris, is the unlock there. Completely agree with that. So, Chris, my man, this was fun. I do a lot of these, and I think this was one of the most tactical and also the right balance of meeting people where they're at, but I also I think helping people see, okay, this is kind of what's in front of me. You know, this is the thing that I and I think I can do that, and maybe I can let some ego things go of I have to do this, or I need to add more headcounts so people know I've managed 40 people, you know, first 20. Um, and I think you've given some really good examples that I hope both, you know, frontline reps and leaders listen to and you know to steal from you, you know, take action on, you know, and pick kind of one thing from the conversation. So, Chris, really appreciate you, my man. And thank you so much for joining me on the show.

SPEAKER_01:

Yeah, thanks, Jake. I've had a great time.

SPEAKER_00:

All right, my friends. That is a wrap on the the episode number, what are we at, 31 of the AI Powered Sellers. So thanks again, Chris. Thank you, everyone, for tuning in, and we will see you on the next one. There we go. Awesome. Oh, great episode. Man, I really enjoyed that. I I was taking notes on some of the topics and really just thinking about the concept of forecasting. You know, how many deals are you hoping to close, but deep down you know they won't? How many deals are we we hanging on to or you know, punishing our reps for because it didn't close, etc.? And I think that that's where AI steps in. And so I think what you hopefully saw here is that AI is gonna help us not only be more effective and efficient, it's gonna take away a lot of the busy work that led to actually, you know, a lack of accurate forecasting or you know, pipeline coverage. So make sure if you're somebody who is a regular listener, I appreciate you. Thank you so much for always tuning in. Make sure if you're new to the channel to subscribe, if you're watching on YouTube or download it on your favorite podcast uh platform. And I'll leave you with this the difference between teams hitting 85% and 120% of quota isn't effort, it's predictability. They're looking at the different parts of their revenue engine and saying, how do I increase X this part to increase predictability? So that's what I got, everyone. Appreciate you as always. Thanks for tuning in to another episode, and I'll see you on the next one.

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Jake Dunlap

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