The CRO Spotlight Podcast

Matthew Darrow Podcast Transcript

Warren Zenna: Hey everybody, this is Warren Zenna. I'm the founder of the CRO Collective, and today I just had a great conversation with our guest, Matthew Darrow. He's the founder of Vivun. Amazing story. You know, Matt kind of went through just an amazing amount of iterations in his company, and watching Vivun pivot with the marketplace has been really fascinating, and he's really smart, and he's got a lot to say.
So listen to this episode. It's really, really exciting and thanks for being here.
So look, thanks for doing this. I know you and I have, I don't know, known each other a long time, kind of go back and forth and watch your organization continue to iterate and develop and grow. And it's really cool to see someone who's saying, "All right, I'm changing things.
I'm working this through." You know? It's very... We do the same, just so you know. Like, we're constantly re-listening to the market and seeing like, what is it that people want? Plus, because again, what we're doing and like what you're doing, there's a lot of people doing the same thing in some respects, right?
And so it's like, how do you find the right mix between the brand and the focus and the ROI and what people are looking for? And then that changes, so you sort of have to continue. So I'd love to hear a bit more about Vivun and the company and its journey and sort of a bit more about how you've managed to navigate through this incredibly strange time we're in right now.

Matthew Darrow: Yeah, it's... Well, we've got a lot of time here because that's a big question that we can go through, Warren. I think the first thing from the highest level for Vivun is we had to completely change our product, our service, and our offering, our go-to-market because of just the transformation to AI.
So my daughter's six and a half, she's my yardstick for the company. And I mention that because I raised the first dollar of the hundred and thirty million raised when she was born. She was born literally like two months after the seed round. And so I know exactly how long we've been at this.
And you know, what we build, ship, and deliver now was based on a lot of the original learnings of the company, but the product is fundamentally different. It is a brand-new thing that we had to go and build. And I was talking to somebody about this the other day where, you know, about two years ago, we said, well, we had a great business going from the SaaS era.
We kinda had to burn the boats. We said it wasn't gonna be good enough to put AI in the SaaS world because of how quickly the world was gonna change. We had to take the learnings and just create an entirely different product in a similar space and go to market, but it has a different buyer, it has a different user, it has a different way to get inside of it.
And that's been the fundamental core, I think, of our transformation. And to your point too, Warren, like, we're experimenting all the time, and I think it's way too early ever to think about declaring victory here. But you know, we're in a world of saying, "How do we do for sales reps what Claude Code did for engineers?" right?
That's kind of what we're up to. But even over the last 18 months, sales leaders and CROs have changed their mindset a ton, and that's why I value the conversations with you so much and your community because... And that's also a perspective I'm curious to get from your side . It's like 18 months ago when you and I were talking, people were still living in this fog of, you know, what was Agentforce gonna do?
What were the labs gonna do? And I think over the last 12 months, that started to solidify, and now leaders are in a very, very different position in terms of how they're trying to approach challenges, how they're thinking about AI. And honestly, one of my favorite things to talk through is, I think psychologically, sales teams and engineering teams are so very different in how they're approaching AI, their excitement or their fatigue or how they're evaluating it.
That's all changed too, and that's what goes into our experimentation because yes, the market is changing, yes, technology is changing, but the folks that have these opinions, their headspace is very different than it was three months ago versus 12 months ago too.

Warren Zenna: No doubt. It's the fastest changing environment I've ever seen. I'm sure I'm not alone in that. Everyone knows this. But it does create problems for commitment. You wanna double down on something, and we're accustomed to doubling down on things that take a long time to build and a big commitment to make, and the data needs to come in to be able to validate it, and all of a sudden the world's changed by the time all that stuff happens.
So there's definitely a big reluctance in the marketplace to make those types of bets right now. You know, before we get into that, 'cause I do wanna talk to you about that, but what's the line through? So when you started this... By the way, I didn't know that your raise was that big.
I'd love to hear more about that. So when you first started Vivun, what was the sort of thesis? Like what were you trying to solve? What was the mission that you ventured after initially, and then how did it evolve and where is it today?

Matthew Darrow: Well, this wasn't really a story of "I was at Company X, had a good idea", the CEO said, "Here's some initial funding, go raise some capital, away you go." You know, I was an engineer turned sales engineer turned product leader, and before founding Vivun, I was actually a little bit burnt out in the B2B tech scene.
And I say that because we'd just gone through an IPO run at Zuora. That's where I was for the last seven years before founding this company, and it was a phenomenal experience. We went from nothing to hundreds of millions of ARR, right, being traded on the public market and learned a lot along the way.
But at the end of that, I was like, "Wow, I gotta take a breather." So I did what any normal person would do, Warren, is I bought a one-way plane ticket to New Zealand with my wife and a small camper van, and I said, "I don't know how long I'm gonna be down here for, but I'm gonna get intentionally bored and think about what we wanna do next."
And I relay this story because at that time, I actually got kind of manic, and I had all this freedom and I said, "You know what I wanna do? I wanna start a family. I wanna start a company. I actually wanna go to rehab a house and rebuild something from scratch." I had all these things I wanted to pursue, which I ended up doing all those things, by the way.
But the idea for Vivun was this really, really simple core thing, which was, hey, you know, I was in this B2B selling universe for fifteen plus years, learning from the best sellers on the planet, from PTC and BMC, right? Kind of the vanguard of how B2B selling works. And I was running these global technical sales organizations, and I never had any tooling built for me, and I never had any tooling not only built for me, but these people were critical to revenue.
So the initial impetus was very simple, which is like, hey, there's a lot of people that are important to revenue generation that have no tooling. We should go fix that. And that's what got the snowball rolling. Now I'll skip... There's a much longer series on the fundraising side of how we put together the funding and the story behind that.
As a first-time founder, that's probably another hour-long discussion we could go through, but I won't bore you here. But the output of that became, we came to market with a SaaS product that was so critical for folks that had complex sales processes, people that had a lot of expertise that needed to be embedded.
So think about companies like Snowflake, Elastic, Cloudera, right? Those types of organizations that had these huge account executives and sales engineering teams working together to drive revenue, that was our sweet spot, and we learned so much about what do those teams need? How do they sell? How do they think about using their organizational institutional knowledge?
How do these teams work together to get deals done? And so when the AI wave came, it was a very natural transition for us to say, "Hey, instead of building SaaS tooling to organize that work and assist that workflow, well, we just need to build a teammate that is part of that group of individuals that we know really, really well."
And that's what allowed us to say, "We're not gonna go this direction anymore. We're gonna go in a very, very brand new direction."

Warren Zenna: Gotcha. So initially what you're doing, I think I'm hearing, is solving the kind of trying to solve the complexity that goes with complex sales and figure out ways to, was it knowledge shared? Was it a desk? Like, how would you describe what it was you were building at that initial stage, if you were to categorize it a bit?

Matthew Darrow: Yeah. I'll take maybe an example that the audience would know really well is something like Snowflake. So Snowflake very famously, right, eight years ago coming on the scenes here exploding, driving consumption. And it was a very technical sale to the point where they effectively had a one-to-one ratio between their account executive and their sales engineer.
And what would happen is these two folks would come together and pair up in a deal to try to figure out, how do I drive consumption? Well, it turns out that workflow is not only kind of hard to orchestrate and manage, but how you drive consumption means it's a lot to do with your product that you have in the market and is the feedback going back into the product to deliver what the market needs to unlock consumption.
The workflow of actually how you drive deals like that looks fundamentally different. And then how you forecast a deal like that looks really different too. So we came on board, and we were this operational layer that said anybody that had technical sales, that had AEs and SEs working together, we were the backbone of not only their process, but then how they would forecast, and then also how they would drive that feedback into the product organization to keep delivering what the market really needed.
And that was our really, really sort of big sweet spot, was those large complex enterprises that had a lot of these specialties that were coming together to make these deals happen.

Warren Zenna: Got it. Got it. Got it. Makes sense. So now AI comes into the picture and I can understand how you can go, "Wow, this could completely revolutionize this idea," right? So what'd you do? Like, what was the way you first initially embraced the artificial intelligence models to enhance your product and what came of that?

Matthew Darrow: Well, I think it's one of those moments where we kind of all remember in tech where we were when the ChatGPT 3.5 release came out where, you know, voice mode was front and center. It was solving math problems. It was doing all these things. And as soon as that came out, it became kinda clear that the curve of how quickly these models would get better, you know, it was gonna be exponential.
And when we sat there and just said, "What does that mean to the space that we've been playing in?" And we're like, "Well, there's a couple things that probably make this true over time." One is there's probably not gonna be a world in the future where humans are going into these bespoke SaaS tools to do their one-off work, to organize their day. And the second thing was, you know, the beauty of all of this knowledge work is you could collapse a lot of these different roles into smaller groups.
Meaning, you know, the reason that a company like a Databricks or a Datadog or a Snowflake or a Cisco, why there's a Workday, why there's 10 people on an enterprise deal, is that there's just too much knowledge for one person to hold at any one time. You have the account executive quarterback, you have the sales engineer technical quarterback, you've got the industry expert, you've got the subject matter expert, you've got the global services deployment expert, you've got the value consultant, right?
You have all these people, and we said, "Well, shoot, actually, some of the roles that are gonna be affected first are gonna be the specialist roles," right? The ones that orient around sort of the core nucleus of the seller or in the world of engineering, sort of the person figuring out what to ship in the product.
So the writing was on the wall for us as like, well, if we just kept plowing forward and saying there's gonna be a lot more AESC pairs in the future, and there's gonna be a lot more need for these SaaS tooling to organize these workflows in the future, right? That was just kind of like a bet that was gonna go nowhere.
So we said, "Okay, well, what is the future gonna look like?" We're very pro-human here, meaning like my future vision was never that robots would be the sales team. I think that sales folks are like even in the AI world, critically important because of the relationship and how they operate.
But everything around that salesperson, the ratios that they're normally running, the types of roles that they need to lean on for help, right? That was all gonna change. So what we ended up doing was we came up with a completely different direction for an idea, and I remember going to my Q2 board meeting, now two years ago, and we presented that.
And we said, "Guys, I don't think we can keep going left anymore. We gotta go right, and here's what right means." And the whole board was behind it, and then we got to building, and we were very fortunate that we had some amazing customers from sort of where we started the company that wanted to be on that journey with us that became some of our initial design partners that are now rolling out across thousands of sellers.
And it's been sort of a fun journey to go through with them.

Warren Zenna: Cool. So now, I'm just asking this question, what does Vivun mean?

Matthew Darrow: Another good one.

Warren Zenna: Vivun?

Matthew Darrow: Why Vivun? So this goes back to the founding story too. So I'll give you the direct answer. I'll tell you the story behind it. It's Finnish for lever. That's what the name means. And so where did this come from? Well, when I was tootling around in New Zealand on my one-way plane ticket in my camper van, figuring out what I was gonna do next, when this idea hit me, I needed to start to figure out, well, how do I put a company in place?
How do I write the first lines of code? How do I get all this infrastructure set up? And the name is always the critical element. You gotta have a good name, and it's gotta be available. Unfortunately, there's no dotcom in the English language that's five to seven characters that's anywhere available.
Even this was six and a half, seven years ago. So what I did was I said, "Well, what's a list of analogies for what we're doing?" And I used a word like lever was one of my top three that I had because the whole notion was, when we started this, this notion that the technical sales organization could be massively leveraged if used correctly in a revenue organization, that's where this metaphor came from.
And the metaphor still holds today because our AI sales teammate gives massive leverage to the revenue organization too. So the lever holds through and through. So I took this term. I went over it. It would've been a lot easier if I had ChatGPT or Claude to work with to do this. This is like an old school version of this exercise.
I go to Google Translate. I put these synonyms and things across multiple different languages. Then I'm going and scouring across GoDaddy and all the domain services, and I'm like, "Well, what's available?" And this one popped up. I registered for it. And actually, funny story, the .co was only available, and I had to go through a brokering process to get a domain name squatter out of Indonesia to get off of my dotcom to finally secure the Vivun.com.
And then sort of the rest was history after that.

Warren Zenna: Thanks again for listening to the CRO Spotlight podcast. We're excited about all the great guests we have, and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free to share the CRO Spotlight podcast with any of your colleagues.
We just think there's a great wealth of information here, and we wanna get the word out to as many people as possible, and your support of the show is really appreciated. I wanted to share information about a program that we offer called the CRO Masters Council. The CRO Masters Council is a bimonthly group of six seasoned chief revenue officers who are looking for a chief revenue officer board of directors, so to speak, that they could share what's going on with them, collaborate with ideas, get some feedback on what's going on in their current role, and these are great conversations.
I facilitate them. The CRO Masters Councils, again, they're twice a month, and they last for at least six months to a year. So if you're interested in having your own CRO suite, your own board of directors of chief revenue officers, it's a private, confidential conversation that we have. It's infinitely useful.
Imagine having a room full of other chief revenue officers you can talk to and say, "Hey, I'm working on this," or, "Have you guys figured that out?" Or, "I'm having this issue right now with my business or my results." These are just invaluable conversations with chief revenue officers. Chief revenue officers have a very, very unique role.
It's a very lonely job, and only other CROs understand what you're going through. So that's why we created this program. So if you're interested in being a member of the next CRO Masters Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me Masters or Masters Council, and I'll follow up with you and set up a call or send you some more information about it.
Looking forward to seeing you there, and thank you.

Warren Zenna: Gotcha. Amazing. I love it, I love it. I love all that stuff. So okay, it's cool. So now today you have an AI assistant, a sales assistant, and you know, I've been playing around with it a little bit, frankly. And I understand it's intended to sort of be a co-pilot of sorts, right? To help you navigate through discussions and dialogue.
But you know, not as a product pitch, but just more I'm curious, how is this an iteration of the Lever and how did this evolve to this point? And what is it? Has your ICP changed? Has it become a different business? This is interesting because as these things navigate, how far do we stray from the original story?
How much do we stay with the original story? It's a fascinating sort of thing we all have to go through, all of us do.

Matthew Darrow: Totally. Well, and I think what's... So I'll give you all the details of how this has morphed over time, because where it is in its current state is very different from where it was twelve months ago and twenty-four months ago. And I think the interesting thing from founders and builders right now is your entire playing field keeps shifting because, you know, in the SaaS era, it was relatively straightforward.
You knew what the incumbents did, you knew what they didn't do, you knew what tools and technology you had available to you, how to create multi-tenant SaaS, how to create mobile applications, how to use a series of APIs and integrations, and then you would go solve a new problem. Relatively straightforward, incredibly oversimplifying the fact of how hard it is to build something from scratch.
But now what's kind of happening is the technology landscape is shifting all the time. Like, things that we could do today, we couldn't do three months ago. And then at the same time, the labs are changing all the time, what they're focused on. And then the incumbents, who normally you could always kind of count on Salesforce being in a certain lane or Microsoft being in a certain lane, like they're all over the place too.
And that's a very, very new sort of playing field to deal with because everything is changing so quickly, and that doesn't even take into account the headspace of the people that are the users out there. So this is this sort of big Rubik's cube that you kind of have to solve here.
So here's where we started. So two-plus years ago, when I mentioned more and then we were like, "Hey, there's not really a future of these SaaS apps that these specialized roles are gonna be collaborating in. You know, that's just not gonna be a thing. So the world has to go to a different place."
One of the things that we felt very strongly about back then was where the LLMs would naturally hit a wall. Like, the fact that, you know, where the next iteration of GPT-4 or 5 or what Claude was doing would eventually tap out. And our point of view was because of how they're built, they're never gonna be great at truly understanding your business in the context of a very specific domain expert.
So back in that day, like about two years ago, we focused a lot on building our own reasoning model for selling. It's our own domain model that is actually, you know, the foundation of a bunch of ontologies and graphs that basically ground the LLM to do something very specific. And so our bet at the time was, well, hey, you know, if you could just produce work running it through this different brain, then that's really where we're gonna play.
So we built this model, and you can see people starting to finally catch on to this, where you're talking about things like graphs and ontologies, brains, like these buzzwords that you're hearing now. That's what people are searching for. They're like, "Hey, just throwing Fable 5 at the problem is powerful, but it's not great for legal or great for medicine or great for, you know, sales."
It doesn't think and rationalize the way that probably you would after such a storied career, Warren, or a doctor of medicine would. So that's what he had to solve. And I think the challenge with that was we're like, "Hey market, we've got a better brain, and it's a sales brain, and it's gonna do better work for sales."
And what we found was the work that we were trying to do, to say it nicely, it's like people didn't care the difference between getting an A or a B-minus on the test. Meaning what we were focused on at first was, "Hey, let me go and do a really great med pick analysis for you. Let me go and build a really great value case for you."
And what happened was they're like, "Ah, I could come to you and get like an A-plus value case, or I could say, I don't wanna learn a new system, I just wanna keep the stack that I have," foundational models, meaning I'm standardizing on ChatGPT or Claude, and Claude does like a B-minus/C-plus job at something like that.
I'm just gonna keep it for that. And we're like, "Huh, unexpected." I was like, "Well, I would've thought that, you know, the higher quality of work people would really gravitate toward." But what they gravitated toward, this is why the psychological dimension is so fascinating, Warren, they gravitate toward humans who don't like change, and they're like, "You know what?
B-minus is worth not changing." So then we're like, okay, so then we're kinda hitting a wall there, and we say, "Okay, well, where do we apply this really powerful reasoning model at a place where an A-plus actually matters?" And what unfolded over time for us, and this wasn't even our initial hypothesis, like customers drug us here, was what you and I are doing right now, which is having a live conversation.
And I think that was the huge unlock for us, which is if you could take the thinking and the reasoning of the world's best seller and insert it into the moment that sales happens, which is the actual live moment between the seller and the customer, that's when A-plus matters, and that's when the business value unlocks, which is execution.
And that's the thing that CROs have been searching for for the dawn of the role. There's more I could say there too, but I just went like that's how that started to change over time. And then there's a lot of interesting findings I could walk you through around what people feel about robots selling to them versus humans and how that's evolved our thinking too.

Warren Zenna: Yeah, and the cool insight, I like that. And I love it. I'm a huge psychology fan. Like, I think about this a lot almost obsessively, frankly. Why do people do what they do, right? That's pretty much the question I'm always looking at. Even myself, why am I doing what I'm doing? I'm just kind of fascinated by it.
And I think you're right. I think that change certainly is something that people don't like. They resist it. They will seek answers that will allow them to stay where they are. They'll look for the answers that actually support their desire to not change. But there are some outliers who want change, and they look for reasons to change, and those are interesting people, right?
It's a really fascinating thing. But you're right. On the whole, I would agree. People tend to be comfortable and they just wanna stay where they're at for a lot of reasons. One of them is fear. "I don't wanna move to a new thing 'cause it's unfamiliar," and unfamiliarity breeds the unknown, and the unknown is the unknown.
Control becomes lost, and I don't know what to do in the face of that, so keep me where I am. Just to see where I am better. And then there are some other people who are like, "It's probably where I am right now. I'm here because I'm comfortable, and I need to move beyond it 'cause I know that there's something else that I'm not thinking about, and the blinders I have on right now are stopping me from seeing the next thing.
So please give me more data to change," right? That's just a different mindset, and unfortunately, there's less of those people, but that's just the way it is. That being said, right, so I would agree too. If I'm in a situation where I'm actually speaking to a customer, and in that real-life situation, someone is in my ear talking to me, they better be right because I can't screw this up, right?
I don't have a window of time to correct it. I have to trust the data and deliver it and think, "Oh, person." You know, it's like when the lawyer asks a dumb question 'cause they didn't know all those facts and they go, "Oh, you asked the question, you revealed the thing." You know, it's like that sort of thing.
So how does it do that? And again, this isn't a product thing, it's more I'm interested in the... 'Cause you mentioned something I just wanna maybe push back on a bit. Maybe I'm wrong, but there are a lot of vertically-oriented products coming out now. The company I know for, frankly, they're building, and there's Harvey, of course, that they're making these vertically focused platforms that are really smart lawyers and smart doctors.
So, you know, you can build a knowledge base up for this. And in fact, like I'm sure you do, I do, I've got an IP bible in my large language model that informs everything, and it gets smarter all the time. So I do think it can be replicated. You just have to borrow it from someplace else. It may not be you, but...
So I don't want to drift off to that, but it's just an interesting idea. I sort of do think that there will eventually become a battle between third-party vertical large language models that are specifically for certain verticalization expertise and just, you know, Claude will come out with Claude for legal, Claude for doctors, Claude for car mechanics, Claude for this, Claude for that, because it's listening to a lot of this data.
It massages it, and eventually it's pretty damn good, right? So I don't know. I mean, I would venture to say my opinion is that the human value is that it's a person. I mean, there's just something like we just know we're talking to a person. You know, I don't know if we're gonna get to a point where a robot's gonna be able to replicate human beings to the point where you don't know the difference. It's the difference between a chatbot.
If a chatbot has good answers and it directs me in the right place in a really smart way, I might go, "Oh, that's nice and surprising. That was a really good chatbot conversation, really helpful." But if I'm having certain types of conversations, I want it to be a person. You know, I wanna press zero and say, "Get me an agent.
Get me a person," right? And I think that's where that magic probably will always live, and that's why I don't think humans are gonna be replaced, and this is a big rabbit hole everyone can go down. But that being said, there is value in having a dashboard in front of me when I'm having a call with somebody.
Like, for example, okay, I'm not doing it now. I sort of don't need it. But let's say there was a dashboard right now in front of me while I'm doing this podcast that says, "Hey, you know, Matt's talking about this right now. Ask him this question." Or, "You know, Warren, there's a really interesting angle here you can reflect right now."
And if it makes me smarter, okay. I mean, it's sort of bionics in a way. It just makes my legs go faster, makes my arms lift twice as much, but I'm still lifting it. It's just I'm being assisted by something, right? How competitive is that space? I gotta imagine there's probably a place that people are playing in right now, and what's the way that you see that playing out?
Matthew Darrow: Yeah. There's... I feel like there's like six good questions in there, Warren, that I want to take the time to answer. I will say, actually, I wanna go back to a story when you talked about press zero to get a human. So like I was doing some remodeling recently. I had some old furniture I had to give away, and I was like, "Oh, I scheduled 1-800-GOT-JUNK."
'Cause I need someone to come and take this stuff away. We've all always used it. And I get a phone call back. It was not announced that this phone call back to me that was gonna confirm my appointment was AI, but you could tell something was off. And I just straight up asked it.
I was like, "Are you AI?" And then it had to disclose itself to me. But everything from mimicking the environment, you could hear keyboard clacking to try to make it go through this, but just these little idiosyncrasies kind of tuned you into that this wasn't necessarily real. I wanna come back to that thought a little bit around humans, like our perception on when we're talking to AI and not, and how that changes our behavior, 'cause that goes right into your question around like what that means for sales individuals in terms of getting help and boosting.
Warren Zenna: Sure. Go for it. Yeah. Answer any way you want. You know, I toss a lot of shit around, I know, sometimes. So don't worry about it. Just answer however you want. I'm interested in your point of view on this.

Matthew Darrow: I'll go from where you started, though, when you talked about these Claude for legal, Claude for this, Claude for that,

Warren Zenna: I think it's happening already, right?

Matthew Darrow: of this too. For sure, even when you see what's happening here. I'll go towards this.
There's a difference between when you give a model access to a lot of data and say, "Become an expert based on data," and actually doing the work to model what an expert does. It might sound a little wonkish, but this was at the core of our research where there's a difference between, you know, every college university has a bunch of textbooks with all the information ever needed inside of those textbooks, but the experts that come out of those universities, they're not all uniformly the same because of how they think of, how they rationalize that information is fundamentally different.
And that's the same in medicine or law or sales, whatever it happens to be. So I bring that up because in the sales world, let me give you a very simple example. Most sales conversations might center around a customer's use case. And that's a very complex related thing because a use case is tied into the customer's pain, which probably is tied into their current state realities, which is probably tied into their future state aspirations, which is also tied into constraints that are preventing them from getting to those future state aspirations.
That use case also is tied into what your product can and can't do to resolve it, as well as tied into actual logical proof points of customers in the wild getting value. Where I'm going with that is you could see how this one very simple concept of use case in a world of selling has a very complex relationship that's not straightforward across all of these other sort of related adjacent ideas.
That's what modeling expertise really means. Like, if you go to an LLM and give it a whole bunch of documentation about your product services, customers are saying, "How would you rationalize this?" It doesn't hold this expertise in its latent space. Like Fable 5 just doesn't hold that.
So you have to give it to the model. So it's not necessarily that people like Harvey in legal or us in sales or, you know, Sierra in service are building different LLMs. What they're saying is these LLMs are really good, but you need to ground them and route them through a chain of reasoning that an expert would use to actually rationalize and solve a problem and attack a problem.
So that's a big piece of how you get to, why is the thing that's gonna show up and talk to you gonna be fundamentally different? Now, flash forward to the call. To your point where you said you gave us a really good visual example here of if I could be talking to somebody and getting something sort of whispered in my ear, is that gonna make me better?
We also, for our team, didn't start up knowing that this would be the logical conclusion. Where we started was, and some of our, more to your point about people liking change, some of our most progressive customers, they said, "You know what? Our vision with you guys isn't necessarily that AI robots will replace our sales organization," because to your point, this is the golden goose of any company.
You don't want to just say, you know, hopefully we make $100 million next quarter, leave it to the robots. Like, that's just never gonna happen. So the whole notion of just letting the robot handle your deal cycle is kind of always a dead-on-arrival concept. But they said, "Hey, I actually want an AI full-blown avatar working like you and I might be here working together on a phone call."
And that was the initial push for us. And what was fascinating is, you know, we've got folks at one of our biggest clients, like at ADP, where you'll get like a 24-year-old kid out of college selling payroll, tax, HR services to a 55-year-old CPA financial sort of planner in Kansas, and there's a gap in terms of the perception of does this young kid actually know what they're talking about?
And this was like a kill zone for an avatar use case where this other thing would come on the phone, which is the expert that can be leaned upon to give trustworthy advice and answers without breaking the sort of relationship that the seller was actually doing. Now, that's still happening today.
Like if you guys... Somebody wants to go out there and you know, it's a great product, go buy ADP. Like you can literally go and have this experience. It's phenomenal. And then DocuSign followed suit with us too. Guidewire followed suit with us, right? These big public companies are doing this.
And then here's what they found. The CEOs were like all about this. This is a way to showcase how forward we are in AI. These teammates are working together. Like, the CEOs are loving it. Boom, boom, boom. Change the market, change the market. And then what they found was, like, this is a great conversation we were having with DocuSign.
Like, they'll go sell to a nonprofit, and the person in the nonprofit is like so not in AI like we are in Silicon Valley. They're like: "Hey, man, I don't... Like this robot, this shit's crazy. Like, what's going on here?" And it became a distraction for them. So we're like, okay, there's like two ends of the spectrum.
There's one end of the spectrum of the people in the market that are actually ready for it. Like, you can do things that fundamentally change the whole mechanics of team structure and then experience with the client. But the reality is like 80% of buyers, they're just not there yet. So what happens is like, well, how do you...
Like where are they? And where they are is they still want that human relationship and the human still wants the support, but you need to give the human the support very passively and sort of like a whisper discreetly behind the scenes. And then that does a couple things. The human gets the great benefit of not needing to extend their sales process by pulling in other resources.
The management chain has lower ratios of support, so the cost of sale goes down, right? All these other great things start to happen. But the humans also start to really trust AI and be like, "Oh shit, this thing actually knows what the hell it's talking about." So then when they're ready to put the robot in front of the customer on the phone with them, they've already bridged that gap of...
It's kind of like, Warren, over your career, like you guys hire a new sales leader and sales guy and gal, and they come on a sales call with you for the first time. You're like, "Oh God, what's this person about to say?" And then when you realize they know what they're talking about, then you get more comfortable with them.

Warren Zenna: Hey, everyone. Wanna thank you again for listening. Get great comments across LinkedIn and other channels about the show, and it's really gratifying to see that we're having an impact on you. Another thing I wanted to let everybody know is that we also produce events. About two and a half years ago, we started these CRO roundtables, predicated on the idea that...
Well, two premises. One is that CROs are looking for other CROs to talk to, which is really true. It's a very lonely job. Now, how do we get a bunch of CROs in a room where they're not being, let's say, disintermediated by panel discussions and sponsorship events and demos and stuff, and really give them a chance to talk to each other?
So we created a roundtable event that is essentially that. It's a three-and-a-half, four-hour discussion between 20 and 30 chief revenue officers, and these are amazing events. The format took off. People love them, and I get requests all the time as to, "When is your next CRO event?" So to that end, I just wanna let y'all know that we have a number of roundtables coming up over next year, over the next, like, 2026.
I wanna share them with you so you can... If they're in your market, you can come. So the next one we're having is gonna be in London, actually, in February. February 24th in London. So if you happen to be a chief revenue officer in the UK or even in Europe and you wanna come by, you'll be hearing about it more on my website and my LinkedIn.
But throw it on your calendar. And then following that, we're probably gonna be doing an event in San Francisco in March. There's gonna be one in New York in March. I'm gonna do another one in Chicago, probably in April. And then I'm gonna do an event in Boston. I'll do an event in Atlanta. I'm gonna do an event in Salt Lake City.
I'm gonna do an event in Austin, and I'm gonna do an event in Los Angeles or the Southern California area. So those dates are to be determined, but they'll be going across all next year and these events are taking on huge momentum. They're the place to be if you're a chief revenue officer and you want to be in a room with no interruptions and have an opportunity to really share with each other in a sort of a private and confidential, open discussion about everything that you wanna talk about as a chief revenue officer and collaborate with great people.
So thank you and thanks for supporting the show and I look forward to seeing you at the events. Bye.
Warren Zenna: Yeah, trust is certainly built over time. I agree. You know, you make a leap of faith, someone passes an interview well, or they do some couple things and you say, "Okay, I'm gonna trust that my instincts were good and I'm gonna throw them on stage and see how it goes." And if they do, you're like, "Okay," breathe a sigh of relief.
We didn't make a dumb mistake, and then they get better, and then now you leave the room altogether, let them run everything for you, right? I agree. It's an interesting point you made, though, 'cause we see this too, by the way, so I don't want to change topics, but we built, I have an agency, a marketing agency as well, and it's another business.
And we built technology. It's an AI platform that solves a search engine optimization problem. It's actually really interesting. Different conversation. But the clients like it, a lot of them, because like they said, there's a mandate from their organization saying, "We gotta do something with AI. This is a perfect example of something we can do," and they can go to market and say, "Look what we're into experimenting.
We're forward-thinking. See? We're doing cool things." That's a very motivating thing for companies to try stuff, 'cause there is the desire to sort of feel like we're moving forward in the marketplace. I think that's an interesting hook for an opportunity to get into companies who right now are still more nascent with these things.
You go to like these companies that you and I deal with most of the time, they're already experimenting with this stuff. There's a huge swath of companies right now that aren't doing anything with this 'cause they don't really know what to do, and given the opportunity, they're like, "This is a great thing."
So I saw it as a big insight in the marketplace, particularly in the non-technical space. It's a great, great opportunity. There's a huge hunger for executives right now to be able to announce that they've adopted some AI platform, and it makes them look good. That being said, it has to work, right?
They're still making an investment in it. And it's almost like there's two KPIs. One is, "Okay, great. It showcases that we're forward-thinking. It showcases we're part of the future. It's good for our organization. It helps our, you know, put some shine on our brand, and it makes us feel more modern." And then that wears out over time.
It's like, "Okay, Steve, we met. Is this working now? I mean, how long are we investing in this idea? Like, people know it already." So if you can do the do thing, you get in the Trojan horses, they wanna feel relevant. Number two is all of a sudden it's like, "Ah, this thing really does work," then you got a double whammy there, and I think that's an interesting thing we're seeing.
But to your point, right? I think it's a really cool idea, and I agree with you. I mean, I don't think people are yet at the point where they're ready to have a robot on the Zoom call with them right now. I think it could just seem like a distraction. You know, people are sort of staring at the robot wondering what it's gonna say next or if it's weird or if it looks bizarre or something like that.
And I think it would take away from the experience. But if it's over your shoulder whispering in your ear and you know it works all the time, you can maybe then the next iteration I can see it being is that it's not on camera, but it's a voice. Like it says things, you know. So it just sounds like someone else is on the call who's just not on video and it's really smart, insightful.
People have some latitude there. And then later on maybe you can say, "You know what? I'm gonna take the veil off. I wanna introduce you to Angie, you know, she's our robot. She's been talking to you for the last 20 hours and she's really smart." But I do think that eventually what'll happen, I think, we're gonna get to a point where I think these things probably are ready for prime time to some degree, and there'll be enough of it that we'll get used to it.
I mean, think about it. There was a time when I went to a website and a little dialogue button popped up and it said, "Hey, welcome." And I was like, "What the fuck is this? I hate this thing." I tried to click it off all the time, you know? Like, it was just ridiculous, you know? Now it's like, okay, you know, I get fine.
You know, I've sort of gotten comfortable with it mainly because instead of answering three questions really poorly and sending me a link to another part of the website, now it actually starts to give me some good stuff, you know, and it's fine. And I think the other part of it too is that we have developed another part of our brains where we're talking to these things all day on our own or how much dialogue are we having every day with these things?
So it becomes a natural part of our consciousness to do this elsewhere. So we're developing another wing in our homes here, you know? And that wing offers a lot of doors for us to enter into and start to use it for different things. I think that we're at a stage where a new sort of thinking, a new UI, a new ergonomic is being created amongst the population that is gonna open itself up to a lot more receptivity to things.
We're gonna allow things into our world a lot faster. It's gonna make us more interested in this stuff. And I think we're just at that point yet where it's still, you know, you and I will probably listen to this episode like 10 years from now. "Remember those days we were laughing about how weird this was?"
You know? Meanwhile, you know, you're a robot and I'm a robot. We're not actually having a conversation, you know? And you know, I think the whole thing is fascinating. That being said, I think I wanted to draw back on something, which was how do you navigate... This is a PLG motion for you now, right?
Is that correct?
Matthew Darrow: Well, both. So there's two... There's the old pincer movement here too, 'cause we've got a top-down motion that's through a normal sales assistant, but then also you can come in bottoms up. The troops on...
Warren Zenna: ...can go in and you can sign up and... Right? Okay. So how do you navigate the mercurial nature of today? Like, you come out with a new thing, it makes a lot of sense, and you can put a lot of investment. You have to build it. It takes time and programming. I don't care how fast it is to make this stuff, it still takes time and investment and commitment.
Now you have to commit to a marketing campaign. You gotta go to the market with it. You gotta talk about it. You gotta say how great it is. You gotta set expectations up. You gotta get customers in it. Three months from now, all of a sudden, you know, it's a totally different world. Like, how's the way in which, as a founder, you navigate this accelerated timeline of things when you're really white-knuckling it?
We are, everyone is. What do...
Matthew Darrow: Yeah. Yeah. Well, this is... we have a big mantra around, like, you know, there's like no sacred cows here, plus also experimentation at the basis of everything that we do. Even if I take the through line of this conversation over the last two years of like what we have gone through since the pivot,
Warren Zenna: Yeah.
Matthew Darrow: You know, I think there's a couple things that fundamentally...
Like from a founder's chair, when I look at myself directing my own organization, like not having a vision that waffles, I think is really important. So you know, at Zuora, I worked for our CEO, Tien, who was one of the first 10 employees at Salesforce, so I always had a very Salesforce-y lineage.
So V2MOM was part of my DNA. That was, you know, Marc Benioff's operating framework: vision, values, methods, obstacles, metrics. We've done one every 12 to 18 months since the inception of Vivun. And actually, what was fascinating is over the last two years, our V2MOM hasn't really changed in terms of the vision, the direction that we were going, in terms of what we were trying to accomplish by being able to bring the most capable teammate to life that's gonna go and radically sort of change how people sell alongside of AI.
Now the things that change quite frequently are like, what are the capabilities that actually spike? How do you go and use the changing market to get in front of people based on where their headspace is? So that's like my case in point of, hey, we made a big bet that said building the brain was gonna be important because otherwise you can't have something that is like an A+ in quality, which is what you need if you're gonna actually move the needle on sales execution in the moment.
And then the other thing is we were going to strategically own the live call moment. And that was something that was never possible in sales before AI. You think about what we used to do, Gong would record a bunch of shit, and then you would read it afterwards and you'd tell the rep, "Why'd you mess that call up?"
Or you know, you put a bunch of crap in Seismic and then you'd say, "Well, did you do your 10 hours of homework this week?" And it's like that world is kind of dead. But like if you wanna change execution, you change it where it happens. You're like, okay, that's what we are pushing toward.
But then, like again, what we've sort of found is, you know, we thought the world was ready for avatars on the call. And even to your point about things being creepy, it's actually not really. Like the technology is quite good and like our work with ADP and others, when you get on the phone with them, there's like no latency, personality baked in.
It's sort of configured to match their personal style. And you... It's kind of hard to tell if it's even, you know, not even a human. But the learning there was that buyers aren't ready for that quite yet. Like there's still, like my 1-800-GOT-JUNK comments around when I called, even though I knew it was AI, she actually did a really nice job of just scheduling the whole pickup.
It went off great and I was a happy camper, but people are still getting used to that too.

Warren Zenna: Yeah, like I said, if it works, it works.

Warren Zenna: Thank you so much again for listening to the CRO Spotlight podcast. This podcast is an important plank in the CRO Collective communication strategy, and we're really thrilled to have such great guests on here. So listening and sharing the podcast with other people is really vital because we wanna get as many people listening to this great stuff as possible.
A couple things to note. If you're an aspiring CRO or a recently hired CRO or even an old, salty CRO, and you're looking to either become a chief revenue officer or improve your chops and gain some more insights and improve your competencies as a chief revenue officer, we offer the CRO Accelerator course.
It's five years now. It's the first CRO-focused course that was out there. It's a 15-week course that is populated by aspiring chief revenue officers and CROs. We're pretty selective in terms of who can be a member of the CRO Accelerator course. It's people who are probably more ready to be a CRO right now.
They have a number of years under their belt as a revenue leader, whether it be a sales leader or a marketing leader or even rev ops leader, and they either wanna move into the C-suite or they're CROs that wanna just make sure that they win in the role. So if you are interested in being a member of the next cohort, please just write me a note on LinkedIn.
Just DM me, CRO Accelerator, and we'll set up a time to talk, and then I can send you more information to give you a brochure of the course. So again, CRO Accelerator course, 15-week program for aspiring and newly hired CROs. Take advantage of it. It's been great, and you'll see some more information about it on the website.
Thanks.

Warren Zenna: It works. I think that's gonna be the test. You know, if I make a phone call and it's a robot and it's good, I don't care. I mean, I just want it to work, you know? You know, a lot of times too, I could see, you know, it's interesting, even interaction with humans is really frustrating, right?
So you know, when you get to these call centers, when you're dealing with things like, I don't know anything, you know. You know, the way they read their scripts and you know, they're trained to be really polite and like to repeat everything to make sure you're hearing me, and it's really annoying, you know.
And if you're like me from New York, you know, it's like, "Would you just please just answer my question? I don't need the 'Yes, so sorry to hear this happened to you. Let's see how we could figure this out.'" You know, it would be really cool if you had, and this is something that would be really fascinating, if you had like, let's say I'm on a call, it happens now, when you get a...
By the way, I thought this was a brilliant idea, and I'm so glad someone came up with this. It was like, you know, pick the kind of music you wanna listen to while you're on hold or zero if you don't want any. That's great. Like, thank you for that choice, right? Zero every time. You know, I don't need fricking music.
But you know, some people might want reggae or something, whatever. It would be cool if it was like, pick the personality type you want this customer service rep to have.

Matthew Darrow: Yeah. So...

Warren Zenna: ...polite and repeated and slow talking, or do you need someone that lives in the Bronx and, you know, was behind the counter selling you a deli sandwich?
I would love that because, you know, this is so easy to do, frankly. You could just program it and say, you know, "Be Ralph from Schenectady," or, "Be Joanna from Idaho," and that's the personality I wanna talk to right now. And you can have the interaction that you want. And I think this is where it gets really interesting.
And similarly, your platform, I could say, "You know, I don't need a lot of fluff. Just give me the five top things I should say right now."
Matthew Darrow: Yep. Yep.
Warren Zenna: ...you know? Or, "Give me the deep dive." That sort of, I think, that sort of personalization, 'cause we can't do that with people. If I meet somebody, I get what I get.
Like, I'm stuck with you. I can't say, "Hey dude, act differently for me. You're annoying me right now." I can't say that to somebody, you know what I mean? I'd like to, frankly, but I'm sort of stuck with what I got. But if I could say, "Look, you know, hold on a second. Program Z, please.
Thank you very much. Okay, thanks. I'm in a rush." I mean, that's... I think there's something really huge there. So I...

Matthew Darrow: I wanted...

Warren Zenna: Go ahead, please.

Matthew Darrow: I wanted to comment on that though, Warren, before you, because you are correct, and actually most people miss this, so I'm glad you brought it up. And what you're describing in personality is almost the same bar of importance of what we talked about, like building reasoning models for how experts truly think.
Because there's twofolds to this. We also published this research paper that showed when you give agents different personality types, they actually do the work differently. So here's a very simple example. You have an AI agent that has access to 10 different tools, and it writes to memory as it's doing its work.
If you make the agent, say, more self-conscious or more sort of biased towards governance, like there's these different parameters you can play with, not only does it respond to you differently, the fascinating thing is it will actually do the work differently. It will have different tools. It will use different information in different ways.
It's not just a veneer over, "Hey, give me an accent from Jersey versus Brooklyn versus SoCal." Actually, how it does the work changes. So this has, again, going back to can you trust AI? Can it do real work? Can it not be a liability? Personality is critically important. So to the point where that's another big push on our front, where even, 'cause I know that you recently downloaded our desktop app.
What's interesting is when you connect the MCP to your Gmail, the first thing it does is it starts to understand your personal tone of communication, and then there's a section inside of the application where you can tune its personality, and then it continues. The more you use it, the more it adapts to you too.
So I'm bringing this up where that's a very internal case of you wanting your team member to kind of mimic and work the way that you would expect it to.

Warren Zenna: And also the way your culture is. I mean, I run my company a certain way, and I want it to act the same way we all do. And I think that's really cool. I mean, this sort of stuff is interesting to me, and I think this is what's gonna end up happening. But you know, we touched on something earlier and I wanna make sure we touch on it, and that is there's two parts to this. You know, the reason why we work together is because we both have an interest in the chief revenue officer as a target for these sorts of things. And this role has changed a lot too, right? This is another whole evolution, right? And to some degree, not at all, like even totally stagnated in some respects.
It's a very weird thing. So in one respect, you've got the role itself that's still frankly very loosely defined. It still hasn't really... It's gotten better. I'd say when I first started doing this six years ago, it was like maybe 10% of CROs were hired, in my opinion, the right way. Now it's like 30, maybe 40.

Matthew Darrow: Mm-hmm.

Warren Zenna: And even still on the fringe of that 30, 40, it's still not exact. You know, sometimes it's like a sales and marketing leader.

Matthew Darrow: Yeah.

Warren Zenna: You know what I mean? Like some will throw two functions at you, you know, sort of thing. Which I think is worse in a lot of ways, but we can get into that another time.
But I'd say what I'm seeing now is more CROs are now, without question, just all they ask about is AI. Like, they just wanna know how do I use it, what's the right way. And they're getting smarter already. Like the speed is better. Like the questions I get now are different than even two months ago.
Now it's like, "Well, I know how to use it. Now what do I do with it?" Then it's like, "We know what to do with it, but why is it not working?" You know? And it's changing quickly and I think that trust is the big issue. I see, like you said, you know, they'll likely trust a Gong or one of these big go-to-market platforms just because why not?
Like a Salesforce or something. And they know this. Like these big companies know they've built that trust and they can get a lot done that way. And does that mean they'll actually do it as good as everybody else? No. In many cases, they're too focused on too many things and they can't be as specialized as they might want, and they throw another product feature in there to get more consumption up, and that's the play.
But you know, there are some companies that do a pretty good job of product extensions, but likely, in my opinion, it's gonna be the more like your type of organizations, you know,

Matthew Darrow: Mm-hmm.
Warren Zenna: ...like the mavericks who are gonna come out from nowhere and kind of build something really great and get lightning in a bottle.
But then, you know, you gotta get it to be bought, and you gotta get it to be circulated and operationalized and accepted and adopted and used properly, and it's gotta be trained. And there's too many dashboards, and who am I talking to? I think the MCP connections make a big difference now. You can connect things. So I think that what we're seeing now at CROs is, you know, what's the decision process of how we determine not what I experiment with, because I can sit here all day on my computer and download something and play with it, but that's just happening in my own world. What's the point at which I introduce it to my organization and say, "Okay, we're gonna use this now"?
And what are the choices? What's the horse race I gotta deal with between other options and stuff? So what are your thoughts on that, and where do you see that happening, not just with your organization, but in general as you're looking at the marketplace?

Matthew Darrow: Well, if I pair this question back to the story that you just told about the marketing work that you've done and the product that you have over there, I think this is a great contrast to answer this question because it's a lot, I don't wanna say riskier, but it's of higher consequence to test and test wrong in the CRO's organization because what you're doing is everybody wants to go and improve seller execution.
Like, that's the whole thing. It's like, how does my rep retire more quota? It's great for everybody. Ramp them...

Warren Zenna: ...revenue acceleration in general. I just want my customers to go through the funnel faster and, you know, I want each stage to be correct, and I wanna know that we end up with the right person at the end of the funnel that we started with, right? That we get to match and that we know why they're buying our product and that we know we can solve their problem, and that when they do, that we do solve their problem.
We can give them more stuff. You know, people just know a piece of that most of the time. They don't know the whole thing. They really don't.

Matthew Darrow: So here's the biggest thing that we run into. Everything that you just described, and this is like a whole conversation that we had is, not only you and I are aligned, but I think all the CROs that you talk to, I talk to, I see in the marketplace, people are not out there trying to delete their revenue factory of interest through close with a robot.
So maybe some small startups that wanna make some headlines, but that's about it. But that's not real for real companies. So everything that happens there is human plus AI. And why I wanna come back to that is that's why the consequences of the valuations are so potentially risky and high because in the marketing world, no offense to marketing, marketing is a smaller team that executes very specific plans and programs.
Even if I looked at, you know, Qualifii that got bought by Salesforce, you know, Craig over there used to be the CMO, now he's back home. But Piper came out and solved this really interesting thing that said, "Hey, you know what? Your SDRs, your inbound SDRs are asleep from, you know, 8:00 p.m. to 6:00 a.m.
So go throw a robot at it 'cause no one's talking to them anyway." Or a marketer might say, "You know, let me automate a sequence and outbound in a more intelligent way. Like, let me go and do that." So these are all very much there's no humans involved because there was never a human manning the ship at that time anyway.
Or at the same time, it was very much contained to one person who could drive an outcome. Now, in the revenue system, you're like, the human ain't going away, so anything to do with AI, you need to fit it into that person's workflow. And here's where the normal objections were that we get all the time. How many tools do they have to toggle between? How will they learn a new workflow? How do I institutionalize something new, not only across 10 reps, but 100, 1,000 individuals in the organization? What type of outcome am I gonna get for it? How do I keep all this maintained? Those questions don't exist when AI can live in a void.
And I see that as that's the hunger that we have as our CROs that we work with. They say, "Hey, you know what? I've been waiting for 18 months for Agentforce to do something for me. It ain't gonna do it. So now I'm gonna go and focus on execution of sales. But to do it, I actually can't just experiment because every time I run an experiment, it takes my rep that should be on the phone with a customer and pulls them out of that brain space for even just a little bit.
So the payoff has gotta be effing massive if I'm gonna ask some sellers to go and do that." So knowing that those are the fears and the boundaries in what we do, at least our approach has always been we run very, very structured small group evaluations because no one is gonna commit to anything that touches revenue if it's not clear that it works.
But also, that allows you to then roll out a broader program where the rollout is just as important and more important than how the technology works. If you can't help manage the change, because it's a change that hits 5,000 sellers, not like one GTM engineer, and that's a balance I think a lot of people are trying to walk.
Warren Zenna: No doubt, no doubt. And that couples with the idea of like, who do I replace? I don't think people are gonna be replaced as much as they say. I think they'll just be augmented. This is an interesting thing. So someone says, which I understand, maybe this is going away a bit, but there was a long period of time it was like, "Oh, we're all gonna be replaced, and you know, it's gonna be so efficient, we're not gonna need as many people anymore."
So I have a different point of view on this, and maybe I'm not really alone in this, but it's worth articulating is, okay, so if I know now, and conceivably, I don't know if it's true yet, but conceivably I can hire somebody, and with these tools I can make them 1,000 times more productive because they can get more done faster or smarter, right?
It's true. Well, then I'd hire more people, 'cause now I have a lot more productive people than just two productive people. 'Cause the productive people will produce more than the savings I'll get on less people. That's just the way it works, right? So I just think more people are gonna get hired. It's just gonna be a different skill set, you know?
So you sort of have to learn this stuff, which everyone also knows. So I think that it's not that jobs are gonna be removed. I think they're just gonna be redistributed elsewhere, you know?

Matthew Darrow: Different, there's... You could also hire a new person too, Warren, that doesn't have 20 years of innate experience. So these tools allow you to have different people that you can bring into the workforce too that maybe you couldn't have before.

Warren Zenna: No doubt. So you know, I think that the only other resistance I see is, you know, I have 20-year-olds, and they both hate AI. You know, they think it's like evil, you know? And meanwhile they're using it. But it's still like an interesting attitude. I think that we need to work through, 'cause there's a cultural, you know, friction there.
They didn't feel that way about the mobile phones. I mean, they wanted one when they were five, you know? But for some reason, this thing just has this sort of dystopian, weird kind of patina to it that's also been, I think, frankly, a bit sold to them. But it's a different planet. So I wanna make sure we don't run out of time here.
So lastly, I wanna just get some point of view on when you're managing your business right now and the way you construct... If you don't mind, what's the size and complexity of your business? Like, how many people and... I'm looking at it more from how you are operating as a leader and building your organization and going through these changes, and what's the way in which you look at it from a go-to-market perspective?

Matthew Darrow: Yeah. So we're 75 people, tens of millions of ARR, so not hundreds of millions of ARR, but bigger than a breadbasket of just a small startup. And our focus is predominantly large enterprises. So those clients like ADP, DocuSign, Guidewire, Dayforce, right? That's our focus and where we go. Big time tech focus.
That's kind of like the scope of, you know, size of people where we are in our journey, customers that we work with.

Warren Zenna: Okay. So you have a CRO or no?

Matthew Darrow: Good question. I hesitate because I did and I made a change when the pivot came because it made a lot of sense when we were in the SaaS era, and as we shifted to this new world, we're rebuilding a go-to-market muscle in a very, very different way.

Warren Zenna: I understand. Okay. Got it. And so you know, again, I don't know. I think that I read this article, I think it was today or yesterday, where like a 30-something percent of big Fortune 500 companies are not having CMOs anymore. They're getting rid of that title. I think there's a way in which I think the C-suite is shrinking, which I think is great for different reasons than people think.
But how we look at leadership in the go-to-market, you know, as companies get more and more complex, it's just an opinion I have, I don't think it's gonna go away, is that you do need someone to steward the go-to-market function. It can't just be the founder. It has to be someone's job. And we think obviously it's the chief revenue officer job.
So, I mean, is that something that you still feel or are you changing your... It doesn't matter. I have no kind of strong opinion about it. I'm just curious to know what yours is. What do you think about it that way? What do you think about it?

Matthew Darrow: I'm aligned to you where somebody still needs to have that seat. I think that the difference, especially in the AI age, like in our SaaS era, we never had a bottoms-up motion. And like we sold the way that, you know, we used to sell at Zuora, or we used to sell at SignalFx or Splunk or something like this.
That doesn't work in the AI era. Like, if somebody can't just come in to experience it, you might as well just take your ball and go home. Like, you're just not even gonna be able to play on the playing field. And I think that's the transition that we've gone through where what that means for the CRO is also equally important, because that person needs to be able to be a phenomenal partner to produce.
Because so much of the revenue and the journey that comes in the door bottoms up that'll drive the enterprise, that starts as a product part of the journey, and I think that partnership becomes really, really important. Not somebody that just thinks about, "Hey, what's the sales number?"
But how does this whole thing work together from somebody coming in free, hitting a credit limit, buying more? What are the triggers in the product that then make them hit the wall to then call sales to then get into the larger expansion, right? Coupled with you're going top-down in a strategic account and strategically using bottoms-up seeding to go and outflank competitors, right?
So now the CRO has new things at their disposal as well, which I think is fascinating for the role too.

Warren Zenna: It's a different, no question, it's a different brain, but it's still... It's the same thing that needs to be solved, just in a more complex way. So fascinated to see how that goes. But you know, I know you probably feel this way too. We can talk for three more hours, but we don't have time.
So we'll have another conversation. We'll have many. But I just wanna, again, I really wanna thank you for being here again. So Matthew Darrow, founder, CEO of Vivun. The product is Hero. And as always, man, always great talking with you. I love it. Thank you so much for being here.

Matthew Darrow: Same here, Warren. Thanks for having me. Talk soon.

Warren Zenna: You got it.