I Trusted AI With Our Brand. Big Mistake.

I always ask people: is the customer banging on your door for the AI agents and stuff, or is it that you internally are pushing those things?

[music]

I doubt that most of the people who said, "No, no, no, we're doing this big AI rebrand," feel the customers pulling them there. You buy software for different functional reasons. They'll say a functional description. They'll say, "Well, I use Salesforce to keep track of all my customer conversations. I'll use Calendarly for scheduling meetings. I use Zoom for all my Zoom calls. I use Slack for team communication." I think when people layer on AI, they have to decide: am I saying the AI helps you do the functional thing that you bought this for better, or are you making a wholesale product positioning pivot where you are now an AI agent company?

All right, Anthony. So one of the first things we do on every episode of the show is I'm going to throw you into a scenario. Waffle Board Analytics, super popular company. They're a Series A DevOps company. They have 16 million in ARR this year against a 14 million forecast that was set at the start of the year. Three weeks ago, they relaunched their homepage. New headline, right? And we've all seen this: "Ship with confidence, scale without limits." And marketing called it the first AI rebrand in the board deck. This quarter's pipeline shows that the website traffic is down 40%, and no one knows why. Their VP of sales opens up ChatGPT, asks it for the best DevOps tool for a 50-person engineering team, but Waffle Board doesn't show up anywhere. But three competitor homepages do. If AI can't quote your homepage to a buyer, is it a positioning problem, or is it something worse?

Ooh, that's a good question. I mean, it really depends, right? It sort of like all things in marketing, it kind of depends, right? If a company thinks there's a new opportunity to be had from some new segment of people who were not the old people that bought them for the old product, sometimes it is worth taking a hit in your conversions in the short term to go after someone new. I'll give you an example. You've probably heard of the company called Klaviyo. They are a publicly traded company. They were positioning themselves for a very long time as a marketing automation platform, specifically for Shopify stores. They repositioned as a CRM for B2C companies, and it was a giant shift. They changed it on the homepage, and you could imagine what would have happened to the conversion rate on that day. Everyone who was coming, who didn't know that much about them, coming for the old marketing automation platform, would have said, "What is this? I thought this was something else. I guess I'm in the wrong place. I don't need a new CRM." And then they would have bounced off. And you could look at that as a giant failure of the repositioning project, like, "Wow, we lost all this traffic." But your traffic on any given day is always going to be the result of all the marketing you already did, you know, six to twelve months, sometimes into multiple years before. People coming to you are going to reflect what you were doing. And so there are moments in a company's life where they say, "We need to drastically reposition for a new group of people, and you're going to lose the old group, but maybe it's worth it to get the new group." In the example you laid out, you know, and I think that's a fictional company, but maybe not. It sounds an awful lot like a lot of the companies we talked to.

It's fictional, but all of our fictional companies are pulled from real stories.

For sure. For sure. In that example, I don't know that it was a smart thing to do, right? A lot of times it feels like a simple renaming exercise while still going after the same underlying fundamental segment that they were going after before, and the new naming made it confusing for that same segment to buy them. So I would say that's probably a positioning problem that they need to figure out.

I'll give another example. There's an artist called Paramore. They're kind of in the pop punk niche. They were very big in the early 2000s. They released probably one of the most seminal albums in the early 2000s for this pop punk genre. And later, they pivoted and they're kind of like funk now, and they have a completely different sound. I saw them at a concert recently, and the concert was called "When We Were Young," and it's this giant festival for people who listen to this music in the early 2000s. They played a bunch of their new songs, and the singer went on this whole long thing. She was like, "It's so amazing to see our fan base is able to change with us." And you just looked around in the audience, which is this massive festival. Nobody was into it, because they had pivoted from one genre to another. And all that had really happened was they had lost a bunch of listeners for the new genre and then gained a bunch of listeners for the new genre. Right? So they lost the old fans, gained new ones. It was not that the old ones came along for the new story. They just got different people. And that's usually what happens when software companies reposition. If they are doing it effectively, they realize: when we change, we're probably just going to lose the old segment and get a new one. It's not that we can take what people think of us as and drastically change it, and all the same people are going to think about us in a new way. It's like almost if you're at a job for a very long time and everyone thinks of you as the guy who does X, and you're like, "I want everyone at this company to think of me as this big leader," and I'm changing. The problem is I've done it for so long. There's nothing I could say that will make him think otherwise.

Exactly. Exactly.

Between that and my executive assistant, he just has gotten used to it.

Always.

Yeah. So like, you would be better off being like, "I'm going to go to another company." It's too hard to shake the old picture of what people have of you to create a new picture. So it's like you're better off just going to a new company. Same thing with these companies. When they reposition, they are not going to win over these old customers to this new thing. They're just going to have to get new people.

And this leads right into the next question I've been thinking about. Like, we hear this all the time. Every board, even some of the CEOs are like, "We need to rebrand our website, rebrand all of our marketing." The BP is like "agentic, AI native, AI powered," whether they believe it or not, or whether they even had a story around it. So I'm curious about a time where you've sat across from a founder and offered feedback not to do that—like, "You may lose your audience, you don't really have the product," et cetera—but they ignored it anyway and shipped it anyway because they're beholden to the board. How has that messaging affected their real goal of improving the revenue or improving whatever they were trying to improve at the time?

Yeah, I mean, we've had some amount of founders for sure. We've worked with a bunch of companies on their positioning, like almost 600 at this point between me and my founder and maybe one or two other people. And I would say over time, as our process and our methodology has gotten better, the amount of people who ship what we suggest has gone up. As we've gotten better, right, more people will ship it because it makes more sense and helps align with what they're trying to do. But like you said, there's always people who won't ship it. And then sometimes we will have people come back to us. They shipped the previous thing that we said not to do, and they'll come back to us and say it didn't work, and we're like, "Yeah, that makes sense." Right? And so it's always a difficult balance because we're essentially talking about the future, right? We're talking about unknowable things of like how the world is going to change and react and stuff like that. So we can only give our best guesses and predictions about what we think is going to happen based on what we've seen. But in general, right, some of those principles I think are true: that like people will not change what they think of you.

And I always ask people like, is the audience, is the customer banging on your door for the AI agents and stuff? Are they the ones driving the fact that every single website now says "AI agents for blank," or is it that you internally are pushing those things? Because I think the difference between push and pull in an entrepreneurial endeavor is pretty strong. Like, if you're getting pulled into something, you know it. I doubt that most of the people who said, "No, no, no, we're doing this big AI rebrand," feel the customers pulling them there.

Is there really though any customer in—I'll say most tech, some services—that doesn't want some type of what I'll say is AI-enabled? And the reason I ask is I'm thinking very specifically to a client that we just helped go through an exit, and one of the primary pieces of feedback was like, "There was no AI. AI didn't exist on the website. AI didn't exist in the talk track. Hell, AI didn't exist in the product if I'm going to be real with you."

Are people really buying products that don't have some layer of AI these days?

I think they are. I mean, the thing is that like, when you look across the...

# Scope of Software That You Use

I know there's people who think like eventually we're just going to have one. You're just going to have your chatbot or whatever and it interfaces with every software.

>> I don't agree.

>> I don't know that we're going to have that happen. Some people say that. I don't think that's next year. I don't think that's in the next five years that all software dies and we just have one terminal. But putting that aside, right? You buy software for different functional reasons, right? Like this should be an obvious thing, but it isn't always obvious. You think of a business, it's made up of a bunch of people in jobs doing tasks. These could be all the way from the CEO level task all the way down to the intern. And they look across these tasks and they say, "Do I need to do these manually or can I get software for it?"

>> Right.

>> I was going to say you're going to geek out because this asks for every single thing. So you think about it and you ask anyone what do you use each of your software platforms for and they will give functional answers. They will not give outcome-based answers. They will not say I use Salesforce to boost my company's revenue. Nobody says that and nobody is going to give credit to Salesforce for boosting their revenue. They'll say a functional description. They'll say, "Well, I use Salesforce to keep track of all my customer conversations. I'll use Calendarly for scheduling meetings. I use Zoom for all my video conferencing calls. I use Slack for team communication." And they're listing these very functional things. So I think when people layer on AI they have to decide: am I saying the AI helps you do the functional thing that you bought this for better, or are you making a wholesale product positioning pivot where you are now an AI agent company?

So we saw a pivot back and forth. This is a company I called Hockey Stack. They were doing attribution.

>> We know them very well.

>> For sure. So they were doing attribution. That was their whole thing. It was like this new way of doing attribution.

>> Then they had this giant pivot and they were like, "Now we are doing agents for revenue stuff." And they did that for a while. And I haven't checked in a little bit, but I think if I go back to it I always type Hockey Stack because my eye's ready for the other team.

>> That's still what they're doing. They're doing really, really well at it. Well, let's see though. Now if you go on their website—

>> Yeah, now if you go on their website, they're back. "Modern attribution that captures the complete buyer journey" is their headline. Whereas if you go back to the Wayback Machine, it was like, "AI agents to do all the stuff for your revenue." From a messaging perspective, they've actually gone back to the attribution functional one. Now, is that because they finished fundraising and now they're like, "Let's go back to what people are buying us for?" I don't know, right? It could be that people treat their homepages as ways to announce new products and they don't realize the implications. Like, "Hey, we just launched AI agents, let's put them on the homepage." Where someone who doesn't know Hockey Stack would say, "You guys are like an AI agent company," and then they have to answer a completely different question of, "Well, why should I use your agent instead of Claude?" Whereas before, if you're an attribution platform, no one would be like, "Should I get Claude or should I get Hockey Stack?" It's functionally in different places in their brain.

So I think that's where AI—I think that the great decision facing software companies is: do we want to talk about AI in the way that it helps them do the functional thing that we do better, or do we want to say, "No, we're making a wholesale pivot and now we are an AI agent company and you're buying us for the agentic capabilities, not for the old functional thing you were buying us for?"

>> Yeah, that's something we could spend all day on, but I want to touch on what you said. You talked about—and I'm going to paraphrase here—but more people are taking your advice now because some of the early stuff you shipped wasn't great. My words, not yours. So on your podcast, while we were doing some research, I found something where you said you feel bad about how rough your process was with your first ten clients. And that quote, "You'd almost send some of them a refund." Without naming one, I would love just to know, because we feel very similar, by the way. Like when I look at our first client, I'm like, "Holy dude, man, we're lucky that check cleared the bank." Tell me about one that went sideways. What did you get wrong?

>> Yeah, I mean I just think our framework was not very robust. So we fell prey to a lot of the same issues that we think other positioning people are still kind of struggling with, which is where you become overly prescriptive in these very narrow ways. So you're like, "If you really want strong positioning, you have to tell me exactly what industry you're going after." And so verticalization, like "We are the X for Y," becomes prescriptive and the clients would push back and we would then push back. And over time, as we got bigger and better at what we're doing, we realized that's actually not the only way to do this. Nor is it the right answer for a lot of people to push people down an industry-specific path. A lot of times, if they don't have industry-specific credibility and expertise, they will get laughed out of the room. Even if they have niched down, right? They're like, "We are the attribution platform for healthcare startups," or something, right? If they go in there, then the healthcare people are like, "So you're for me, a healthcare person? What are you guys like, MDs in your background?" And they're like, "Oh, no, we just picked this industry because we have a client concentration." They're like, "Do you even understand healthcare?" They're like, "No, not really." That's not going to be helpful.

So knowing that now—that narrowing in an industry-specific way is not always the right answer. And so just, like, our framework has gotten so much more robust. In the beginning, we were sort of building it based off of a lot of the other ones that you've seen out there that kind of look like almost Mad Libs: "We are X type of company for Y type of customer in Z industry," you know, these kind of very long sentences like that. The funny thing is, like, if you try to fill these out for real companies, you're like, half of these are blank. Half the companies didn't do this. They didn't pick an industry and a department and blah blah blah, and that's how they got big. They segmented in very different ways. And some of those different ways we just didn't have a vocabulary to talk about them that we now do. And we have a way better lens of exploring it and showing it to the clients to really figure out what really is the range of options that would make sense. Yes, maybe verticalizing in one industry is one of the options, but more often than not, it's actually not one of the options.

>> Here's something I keep seeing with sales teams I work with. Generic sequences don't work anymore. We've all gotten so good at tuning out the noise that even your own buyers are ignoring you. The problem isn't your reps. It's that your sequences are static and your signals are somewhere else entirely. That's why our clients use Nooks. And the thing that stuck with me is that their sequences actually stay fresh because the signals update them automatically. Right buyer, right moment with no manual babysitting. If your outbound feels like it's shouting into a void, go check them out at nooks.ai/thebridge.

I'm a little curious as you've progressed. So you've built your framework, but I understand all the Mad Libs—like, we've gone through brain exercises and framework exercises actually twice since we've been around, just because things evolve. And actually it's changing even faster now. It's like, every three months things, new competitors, everything's changing. So are you finding that customers are coming to you more often to try to rebrand or have a conversation about that? And as a part B to that question: are you injecting more AI ability into the framework so you can speed up that process?

>> Yeah, I mean, because we are so singleminded and narrowed into what we do and who we're for, pretty much every sales call runs the same way. People come on and they say, "I'm rewriting my homepage or doing a website revamp and I need to figure out our product positioning." And they usually have been following us for a long time. Though I will say we are getting more people coming in from Claude and ChatGPT and stuff, which is really cool. But they come in basically knowing that they have some level of a positioning problem, which falls into different buckets. It's like, people read our website but they don't get it, or they do get it but they don't know why they should pick us over the other people, or all of our teams explain us in a completely different way. And it's usually like the trigger is like maybe a fundraising round or a hiring of a new head of marketing. People coming in and they're like, "Before we do all this new stuff, spend all this money, do we even have a unified..."

What's the story that we're going to tell? So that's usually like the problem people come to us trying to solve. We do this two-week sprint with them, and then they feel like they have the story and the narrative. Then it gets documented and rewritten on a homepage to put throughout the rest of their marketing, which we don't touch, right? We don't really have an upsell. There's no retainer. There's nothing. It's really just this two-week sprint we do with each company, and that's basically it.

To your second question about AI, we use it a little. Probably not as much as we could. We've ping-ponged back and forth. It's like the better I get at positioning, the less I need the AI. I will say the AI stuff has helped with synthesis of large amounts of research. So for example, pre-AI, we would watch every sales call that the companies would send us, and we were really only able to watch like one or two, right? Because just of time constraints—it'd be like an hour-long call. But now they could give us 10, 20 calls, and we could use the AI to ask questions across all of them, looking for very specific things: how they're perceived, what people are asking for, and how they describe themselves. So I think that type of stuff has really drastically sped things up.

But in a lot of ways, it's still sometimes faster to just type the stuff ourselves, you know? Going back and forth with the prompting, you don't have to think as hard because you're offloading the thinking. You end up sometimes spending more time. For example, if I write a sample hero—like an H1 in the body of a specific positioning strategy to help the company know if this is a strategy they want to take—we'll usually give them a sample. This is what it would look like on your website if you did this strategy. Here's the headline and here's the body. To get that down, sometimes I just write it because I'm pretty fast. If I ask AI and give it more context, there's probably ways we can do it better. We're like talking to some AI-native consultancy folks who are trying to help us really create things for this bespoke work. But just using them off-the-shelf sometimes, it's just faster to do it yourself.

I don't think there's an off-the-shelf thing, and I think it will evolve. Yeah, I appreciate that because we've been thinking about it a lot. We do a lot of repetitive stuff, and I do think gathering all the data and consolidating it into a digestible piece—then you've got to trust that it's doing it properly.

I wanted to move over real quickly. We run into this problem a lot as well. I think there's a lot of parallels here. Some of the biggest obstacles, as you've mentioned, is moving from a founder sales motion to a company-led sales motion. Most of the leads are falling in, and a lot of people want to talk to the founder directly. It's easier for the founder to make that motion more successful, and then you bring in somebody else, and it's not successful. The founder is like, "The salesperson sucks," or whatever it is. But that's not really the case. I'm curious what advice you've given yourself or to founders in positioning their company and giving yourself and Rob how to position your own company.

Yeah, I think with founders, the biggest thing is showing them that they are tailoring the story differently for almost every one of their customers. In founder-led world, it is incredibly rare that the founder is like, "I am going to market with one specific narrative and all my sales calls look the same." It's almost always, "I am getting introductions through my VC network or through my personal network to all sorts of different companies with all sorts of different problems and pain points, and I am able to—because I'm the founder—tell a different positioning narrative for every single customer." You have the passion around it. You have the passion around knowing exactly what you're doing. It's just very difficult to replicate.

Yeah, I think when you're telling these stories, right? I always try to remind people: okay, so we're going to go to market. Now we want to scale beyond just me. So I hired an AE or an SDR, right? Out of high school. And they're like, when I look back at all of our customers, I've been selling to the C-suite. So we probably need to write the message for the C-suite for all these enterprises we're going to try to sell into. And I always say, okay, so when you've got this 18-year-old SDR, they're going to cold call a CEO of an enterprise company and you think they're going to get through to them and then be able to hang on the call with them and have a meaningful conversation? And I ask, how did you get introduced to all those CEOs? Did you cold call them or cold email them? No, our VC intro'd us. No, this guy I used to work for, he was... and it's always the case that way.

So you say, okay, so if we remove your personal network... and I'll say, because you want this to scale, right? Like, how many more CEOs are you friends with? Have you gone through them all? And usually they're like, yeah. And I'm like, I mean, maybe you could go and make a bunch more friends. Like, you could join some country clubs, get out, hit the golf course, and that can be your go-to-market. Like, it sounded like you wanted to do this, right? Like, bring in account executives and people to do this who aren't you. So we're not going to be able to rely on your personal network or your VC network. Okay, so then let's back up and say, what's going to be our most likely entry point to get conversations? Well, say you want to land Salesforce as your customer, right? You're going to try to go to Marc Benioff? Come on. There's way more directors who probably would take a call with your AEs. So you're like, I want to sell this big enterprise, but I couldn't get through to this guy or this guy, but maybe these people over here I could get through to them.

I think Marc just picks up cold calls all the time.

I'm sure he does, right? From STRs and AEs and stuff, especially the AI STRs. I'm sure he loves chatting with them too, you know.

And then your other question, Dale, was around our service. We try, as much as we can, to let the marketing do the heavy lifting and put everything out that we can to make it very, very clear: what do we do? How do we work? What do we cost? So by the time they get on a call, they're kind of already bought in, and we can have all those sales calls run effectively the exact same way.

A process. Imagine that.

Let's shift to the Triple M—Anthony, which is what we call our Monday morning move. This is a practical takeaway that our listeners can start Monday morning when they hear this. And I'd love to know what you would add, change, push back on, or just tell me, Adam, you're right—which never really happens, but I'm happy to take it.

All right. So this week, what I want people to do is open their homepage and look at it through a lens like you've never seen it before. Read only H1 and H2—so your headline and your sub-headline—out loud. If you can't then say in one sentence who it's for and when they'd use it, that is not a marketing problem. That is an alignment problem at the top.

You then need to get your exec team in a room—not just marketing, every person on the exec team—and have them write down on their own in one sentence who this is for and what does it solve. Then compare answers before anyone says another damn word.

After all of that, paste it in AI and ask AI to describe your company to a buyer because I promise you, if you can't do it and your executives can't do it, AI isn't going to recommend you either. This isn't a copywriting problem. It's a problem of whether the people running the company actually know, and Dale and I talk about this a lot, their ICP, the problem they solve, and the messaging used to describe it.

I love it. I would add just one more thing. I think this is kind of like one of our probably the biggest insights from all the projects we've done: it's that people think of things in terms of categories, right? We categorize everything in our life. This is my car. These are my shoes. This is my wife. This is my son. We put everything in categories to help make sense of the world.

Software is a category—just software itself—but it's an incredibly diffuse and diverse category, right? It's like saying goods or services, right? It's so vague that it doesn't mean anything.

So when people are evaluating the website of a software company, they are trying to figure out: is this a type of software that I have seen before or is this something new? And so that question is answered sort of from a category perspective. Are you a company in an existing category or are you trying to create a new category?

And you will see slices of this. I was just talking to a company that basically has a CRM but is not just a CRM. They're...

# Selling a Platform with Confusing Messaging

Selling a platform that includes a CRM among other things. So because of this, their messaging is super confusing. You'll see things high level, just not go high level. Oh man, they'd be a good client though. Good logo to have on there.

People will take three or four different product categories and sort of sell them separately but then also say that they are a platform, which becomes really confusing because then people are trying to figure out, "Wait a minute, what does this replace of what I have? Is this something new? Like, do I need to get rid of my CRM to buy this?" It's unclear.

So in your exercise, the thing I would ask everyone to do is to say, are we positioning ourselves primarily in a mature existing category, or are we primarily trying to put out a new category that doesn't exist yet? And if so, what is it and what is it for? And I think that question really creates a lot of clarity in the fact that there is a lack of clarity.

You'll get some people who will be like, "Well, yeah, we're a CRM. I'm on sales calls every day. I'm getting compared to HubSpot." And the other person's like, "No, no, no. We're not a CRM. We're fundamentally a different thing. We're a new platform." And then you're like, "Okay, well, what's that new platform for?" And they're like, "Well, lots of stuff, right?" And then you get this ambiguity.

# Uncensored Questions

I love that. That's a really good add. We do this thing called uncensored questions. So we're going to kind of rapid fire a couple questions at you and see how you handle them.

This first one does not necessarily need to be a customer. What's the worst homepage you've seen of a company that raised more money than it deserves?

Oh my gosh. We have a whole Slack channel. We have so many. I just did a post about this, so you can go look at it if anyone wants to check out my LinkedIn. I was looking at four years of the last homepages of the company Gong, which I really like the company. I like what they've done for the world. I like that they've kind of ushered in this whole call recording thing, which has made my life so much easier. I'm not a Gong customer, but I looked at four years of their homepage and four different heroes and they create a new category every year. Every single year they come up with a new category. And I always am like, man, it's crazy.

Because I think of someone like, well, think of Salesforce. I'm pretty sure their stock ticker has been CRM since I don't know, the early 2000s, and they're not creating a new category every year. But maybe Gong is. Maybe it's working, maybe it's not. I would assume it's probably not working because the idea of creating categories that stick and you're like the leader of it—so if you have to change it every single year, maybe it's not working.

So that's probably one of the more recent ones, but there are so many. It is not difficult to find terrible, confusing B2B software companies.

# A Loaded Question

Here's a loaded one and I don't know if you're going to answer this: Name one of those ten clients from the first ten that you would generally refund if they called you and asked you to do so today.

Has it been long enough that we could do that? Or name the industry or the problem.

I'll go one further. I won't force you to throw a name out there.

I mean, I think it's possible that we did refund some of the people in the early days, or like I think we maybe refunded some of the process. I would have to go back to find a specific one. I remember we did a project with this guy with a company called Yobi. It was Y-O-B-I. And they were probably one of the first, maybe the first or second. I don't even think we ever finished. Basically, the project just ended and I think he just ghosted us and didn't even reply.

I love that you gave the name and gave the refund.

Yeah, I think we did.

# Final Question

I'm going to give you a super simple one to finalize this: Dream vacation destination.

Oh man. Always his favorite.

Oh man, I don't know. I'm more of like an out in the mountains kind of guy, I think, than I am a beach kind of guy. But I don't know, as I get older, I just—I have two young kids, so travel is significantly harder with two young children. So now I'm like, the vacation would be they all leave and I'm just at home. That's probably the dream vacation this year.

# Where to Learn More

Anthony, where can people learn more about you and your company?

Yeah, my LinkedIn would be a great place to start. I think secondarily is our website, fletchpm.com. We just launched a newsletter and we've done maybe five or six longer writeups. That's the main thing that we're pushing people towards. It's like one step deeper than the LinkedIn posts. LinkedIn posts are always very ephemeral.

We will backlink that in our show notes for you to try to get you some subscribers. Anthony, thank you so much for joining the show, sir.

Thanks very much for having me. This is Sublab.