The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

326exchanges match
235on raw tape
19redirected or not addressed
Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q a difference? Like Box, when you joined Box was still at four hundred million, or I mean, it's a well-established brand, right? So from the front lines, what, before this change in messaging, because you're saying it worked, you picked it number one, so obviously it did work. What were you saying before? What was the team saying before, and how did that How did that change, um, in practice?

A I think, um, a lot of the underlying message was similar, but from a messaging standpoint, we were, we were really on this category shifting journey. So the market that we helped create became known as EFSS, um, electronic file sync and share. And we were helping to evangelize sort of the new cloud version of that category around cloud content management. And so we're having lots of conversations about this sort of journey from the old market EFSS to the modern market. Being CCM, Cloud Content Management, and that from a category shifting and shaping standpoint really makes a lot of sense, and there's a lot of merit to it, but You know, from my experience, when we would talk about cloud content management for seasoned IT buyers that maybe, uh, went down the ECM path, enterprise content management, and implemented those client server tools, uh, that created a little bit of confusion because then they would want to sort of compare the feature set of the old established, 19 nineties ECM category with this new cloud content management version. And then you're constantly in this like never ending feature comparison of an old model versus a new model. Which I don't think was as effective as a crisp and clear message around the content cloud.

AI assessment note: “we were really on this category shifting journey... from the old market EFSS”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q right? What, um, What does it mean? What are you seeing on the front lines in practice? What does that mean? Like are, are, are, can you, can you capture more budget for box if you can capture some of these adjacent spaces or how is it, is it, they want to concentrate the same budget and fewer vendors or who's benefiting and who isn't from that, from that consolidation?

A Well, I think that the extra large vendors will benefit big time as they did in the client server era. And so if you think about the number one and the number two cloud investments at the app layer, not the infrastructure layer that organizations are making at Microsoft and Salesforce. They will certainly benefit from consolidation waves and they'll acquire companies that a lot of those point solutions, uh, will get gobbled up in their portfolios as we've been seen for years. We, we would be sort of an upper middle size cloud, if you will, and maybe a, a large sort of a cloud. And, and so for us, uh, we're in this space where we can be a consolidate or, or we can be consolidated. And certainly we prefer the opportunity to be a consolidate, or if we have a credible, um, Path to help a CIO sort of shrink spend in their SaaS portfolio. And so if you think about us in our core content cloud market, you know, this year, as you know, we added electronic signature to the platform. And that's a really exciting move for us because, you know, it's our belief that electronic signature should be part of your content cloud, not another app that you have to go by. And so I think that for us, it's going to be a combination of lots of net new wins as we broaden the portfolio around content oriented use cases. And then massive improvement in our renewal rates as we give customers more and more …

AI assessment note: “Well, I think that the extra large vendors will benefit big time”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q mean in practice? How did you make, how did, how did you come in and get more folks on team blue? Like what, what besides, and we can talk a little bit about this, this, this tweak to sales comp plans, but that's not really what you're hitting here. You're getting all the functional areas to, to, to buy in and how did, how did you do this in practice?

A Uh, so I think it was the renewals team, and just to correct my color in here, the customer success team that were kind of bearing the brunt of renewals, and the rest of the organization knew it was important, but, but, um, But they weren't, they weren't, they weren't in their hearts and minds understanding that I have a role to play in this. So I think it was just really repeating the message and then getting alignment across the executive team. And, and whether that was our chief product officer, our CEO, Aaron, our CFO, Dylan, our COO, my boss, Steph, like all of us just repeating this over and over and over again, that we're all in the renewals team and everyone highlighting over and over and over again, how important it is for customers to be successful. And when they are successful, they renew. And so we, and we did make the comp changes. We did change all of our operational practices around the Around the way we measure renewals, uh, you know, all the calls and meetings that we have to review those dashboards and hold teams accountable and have interlocks and have clarity on where that number is and where we have risks. I think that the, because we had a relatively small team that really was waking up every day and thinking about renewals because of our book of business, they could only look out, you know, maybe three or five or six months at their book of business, in w…

AI assessment note: “repeating the message and then getting alignment across the executive team”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q and prioritize and pressure to ship faster. Aren't we all under that pressure, right? Um, yeah. Um, and do you find just the penultimate B, do you find that because of this customers are more demanding in terms of when they want those enterprise style commits to come, or are they still willing to wait two to three quarters for what you, what the CEO agreed to in the contract?

A I, I think the customers, that's what well said. I think the Customers are willing to wait, but they want certainty that is more than the agile model delivers. This is a real hard problem. They're used to the old model of, Hey, it's going to ship in Q three of 20, 22. And it's like, I don't know what I'm shipping next week. This is agile. We're, we're not trying to set the future. And so I think that, but the client view is actually reasonable because they're, they have these training cycles. They have the, if you have sell to big customers, they have to train their users. They have to do change management. And so there's this constant battle of like agile, not wanting to have date commits and customers wanting date commits and you have this just back and forth all the time. That's a big challenge.

AI assessment note: “I think the Customers are willing to wait, but they want certainty”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q Yup. The next one, it's a bit of a layup or even a commercial, but I always love to hear what a CEO has to say, which is, uh, what, which new Coupa product or feature are you most excited about?

A Well, the most exciting one for me is community intelligence, which is a set of capabilities that we discuss in the book, but they're in the entire fabric of the product set. So they appear, for example, in expense management, which we don't talk about as often, but we have the hundreds of customers using Coupa expense management. We are mitigating fraud in expense management. We're using the data set of our aggregated customer base and serving up, uh, individuals that are highest likely to be doing fraudulent activities so you can investigate. Rather than rigid kind of, you know, policies or a free-for-all, we found a way to use technology to be prescriptive, which is the P in Coupa, prescriptive to, uh, to, uh, individual, uh, controllers and people responsible for, for spending in a company, leveraging community intelligence. And that's just one example of, of, of many capabilities, leveraging community intelligence within Coupa.

AI assessment note: “Well, the most exciting one for me is community intelligence”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q 50%, right? It's hard to even tell on this chart. It's 26. I mean, it's low, but like, it seems like a long time ago, but like the mood was so gloomy in February 2016. People thought it was over. A leading VC who I love was throwing unicorns at the founder saying that unicorns were dead. Uh, it seemed pretty bad for like 13 days in 2016, didn't it?

A Yeah, that was a ServiceNow and LinkedIn missed their quarters. There was some fear that it was going to roll through, fell 30%, and we'd fully recovered by December. It was a, it was sort of a false crash on, um, signals that, uh, people overread. Um, uh, this by contrast is the fastest 30% plus decline, um, by the broad market in history. I mean, this beats the, the great depression, the oh, wait, the dot com, et cetera. Um, so the, the magnitude and speed of this pullback across all sectors, not just tech, is unprecedented. Uh, the, the good news is that it is driven by this external, um, shock that will have a finite end. Uh, it, it's not the unknown like the housing crisis was or the, or the Great Depression where you had a whole economic, you know, complex equation unwind. In this case, a vaccine will ultimately solve this. The problem is that will probably take, you know, experts are saying nine to 18 months to mass produce, and so you could have this huge economic lag that's dependent on that, and then a, a rebound cycle that's unknown, uh, even after that, and so, um, I think from a total market perspective, uh, you know, we have to be pretty conservative in our expectations, but from a multiple perspective, I think that the thing to call out here is, even after this pullback, We're still looking at, you know, eight, nine, 10 X multiples in the public markets on revenu…

AI assessment note: “Yeah, that was a ServiceNow and LinkedIn missed their quarters.”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q a lot of loyalty to because they did so much. How do you, ah, we, we, we know in our guts, but from a process perspective, how do we put that in practice with our teams? How do we, how do we know how to, can we measure this toxicity? Can we, is it, and how do we, how do we optimize the action, ah, that we take on it?

A So part of what you have to define is what toxicity means to your organization, right? So for us, it's really focused on culture. So we define what our culture is, and then we can actually talk to someone about the degree to which they're falling short or exceeding those values. Part of the benefit of the anonymous employee survey is you hear very quickly from people's peers who those toxic folks are. And so I already mentioned, we share all the data that's received, including things about our management team. So if there are things about me or Darmeshin there, they're shared with the whole company. Anyone on the management team signs up for that. But if we receive anonymous feedback about one employee who is a frontline employee or a frontline manager, we go directly to that employee, and we say, we just want you to know there were five comments in this round of the ENPS just about your behavior. And we go to their manager, and we have a conversation, and we're like, ok, sometimes that's people reacting to change. Sometimes people don't like being challenged. So some of those people can be our best employees. And it's my job to have the conversation and go, ok, Is this person just pushing the status quo? If so, let's help them do that in a way that feels more relevant, and kind, and contextual to the people they're working with. If that person is truly toxic, we need to help p…

AI assessment note: “Part of the benefit of the anonymous employee survey is you hear very quickly”

Answered raw tape D 5 · C 5 · P 4 · Cm 5 4.75

Q Got it. And did you, I know it's a little bit nerdy or tactical, but did you put new GMs in charge of it? Did you create little pods? How did you attack these different verticals?

A I would think of them more as campaigns. So we said, okay, we want to go win in field service, or we want to go in construction. Let's go understand the customer. Let's, we have to build some technology partnerships because they would integrate with different pieces of software. So let's go do that. Let's of course speak their language, right? So when we're doing marketing case studies, but we never specialized the sales team and we never specialized the product teams, except for public sector. Public sector has a different buying cycle, right? And they have like different contracts. So government sales is a little different for us. But it's the same use cases. So we try to sell the same products across the board, in other words.

AI assessment note: “we never specialized the sales team and we never specialized the product teams”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q could, could help Plan the agents. Who's responsible for the agent? When it's just a human make taking the action of Rubik, the human's response. I mean, if Rubik has a bug, that's on you, right? But if the human makes a mistake, it's on the human. When you have these agents out there, this is not Sastra pulling up a parking pass application. Who's, who's, is it the GSI?

A I mean, at the end of the day, we're still responsible. Even when, when a customer makes a mistake and something isn't working, they blame us and rightfully so. They should. It's our responsibility to make it obvious what the right choices are. And today people do make mistakes because there's so much complexity in setting up our product. And even though we have constantly sold on a message of simplicity and we have beautiful design experience and all this stuff, it's still people can make mistakes and people are going to make mistakes more than agents if we build our agents with the right guardrails around it. And so our belief is that actually we'll make fewer mistakes in an agentic world We'll tell people what the right solution is. We'll keep, take more of the guesswork out of the equation, which there's a lot of guesswork, a lot of different ways you could configure things, give them best practices, and that will actually yield better outcomes for them.

AI assessment note: “I mean, at the end of the day, we're still responsible.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Has that changed in the age of AI? Are they looking for something different? What, what, how has the urgency changed or the discussion changed with BIOS?

A I think urgency has changed significantly, right? Like, um, we used to joke about this that in the, you know, Databricks has been a data and AI company now for what, like, 13 years at this point, and we used to have to, we would scream the data part, we'd whisper AI, because AI people were like, that means like self-driving cars and iRobot, who cares? And so everybody wanted to do it, but if the answer was, look, I want to bring in my data and it's helping me replace my data warehouse or my data engineering system to be able to get good analytics and fun. Now what's happened is everybody's like AI is a top line imperative. I need to use AI. I want to drive all of it. And they immediately run into the problem of you'll hear different words. Like I have data silos. I need an ontology. I need a semantic layer. I need context. Right. And what they've realized is what's actually really, really hard for in order to get AI work, I have to break down all those different silos. I have to understand, make my data high quality and be able to be accessible to agents, not human to really transform this. So the urgency of I need to kind of get my data state in order and governance around it and context has gone through the roof because people realize without that, they can't actually get AI to work in any meaningful way.

AI assessment note: “I think urgency has changed significantly, right?”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q classily great at going into a room and saying, we will solve your problem for putting your data on the cloud. We were just going to solve the problem. What's that Databricks pitch today? So they have this anxiety. They want to get ready for agents. They want to get their data. What, how are you, what's the pitch that the big problem you're solving for the stressed out CIO?

A So I think that there's a couple of different points. You talk to every organization. They're like, AI is going to transform it. I want intelligent apps. And by the way, I don't want intelligent apps, just my engineering team, what it's building. I want sales. I want finance. I want my like merchandising team, all of those being able to use it, but I struggle. I can't today. And the main reasons that they say it is like. A, there's way too many things to choose from. Like I have, am I picking one of the different hyperscalers? Is the right answer gonna be, do I pick anthropic? Do I pick, uh, open AI? Do I pick Gemini? Do I pick open source? So one is like, which one of those do I build on to move forward? Second, like my data spread out, help me there. Third is, can you actually talk to me about context? And context is different than data. Think about it as you're onboarding a new employee. How do you explain Everything that goes on in your organization so they can operate effectively. How do you get back? Cause that's what agents are. Um, and then lastly, how do I control this? Cause agents sound great, but my favorite was everybody was like open claws out. So what I did is I took a Mac mini, disconnected it from the internet and put open claw on it. And I was like, great. Congratulations. What does that do? So how do I unleash all of these, but make sure that governance works…

AI assessment note: “And so the Databricks pitch is like... We break down all the different silos.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I know what, but How in 2026, what does that mean to a CIO? What do they, and maybe what that really means, I assume what that means is they want to do more with their data than they could do before, but context is super important for agents, but I want to know what does 95% of the world mean when they want you to help them with context?

A Yeah, so look, I think that there's a couple of different ways to think about it. There is one in some organizations that you have, especially if you're in a regulated industry, like I was meeting with a large bank yesterday, and the answer is if somebody wants to, let's call it talk to their data and ask questions, when you say, hey, show me what does my revenue look like, or what is my loss, like, those are not just a table called revenue. They have very, very clear definitions, right? And so you want to be able to map those somewhere, which is like, these are our core terminologies of what it means to our industry and our world. I think that's one. The second thing is though, there's a lot of different things that are kind of Let's call it shorthand that is not captured somewhere. I'll give you a very simple answer. If I ask, ah, you know, I'm talking to my data and I say, hey, can you show me in the last fiscal year, what basically my top spenders were on the major clouds that we support, ah, at the end of the last, like fiscal quarter in EMEA, what's the answer? Sounds like a simple thing. Anybody at Databricks would know what I mean, but then it's like, what does he mean by clouds? What is fiscal quarter? What is their fiscal quarter? What is inside of EMEA? How do you think about top spenders? Like, These are all ones that you, if you were normally in the company, you're…

AI assessment note: “these are our core terminologies of what it means to our industry and our world.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What are folks exaggerating, getting a little bit wrong? What are you seeing for real from the front lines?

A Look, I think if you sit on X, it's kind of interesting. You'd get this viewpoint that everybody has figured out, you know, AI, everybody's building their own LLM resource agent to do everything. Yep. I think the rest of the world is definitely a little bit different. You know, still how many of them actually properly adopted AI in the way of coding tools or like systems is pretty nascent. But every one of them, we were talking about this backstage is realizing Every CEO says, if we are not adopting AI, we are behind, right? And so now you have all of them telling their employees, if you're not using AI, we are behind. You've got to figure it out. We're going to measure your performance by it. Go use tokens. And so now we have this other problem, which is happening where everybody's like, okay, all my employees are token maxing. My spend on tokens is going up, but I have no idea what I'm getting out for it. Right? So I think everybody realizes how important AI is outside of the We're gonna give them access to pick one of the models, and we're gonna start using coding in our engineering team. It's still early days for many of them, and they're all looking for how do we redesign our processes, and how do we actually think about governance and data to make AI work well, right? So, I mean, that's what we at least see in many of the organizations we work with.

AI assessment note: “You'd get this viewpoint that everybody has figured out... rest of the world is definitely a little bit different”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q the whole world for him. Like it was crazy. And then for it's 18.2, because he literally has maxed out the global market share for what he has. Do you ever think about, because Calumni is a little bit like that and that every, I mean, everybody uses it, right? Is there some magical number of knowledge workers that Talendly today can access? And do you have all of them?

A We do not. We definitely do not have all of them. So if you have family members out there, friends, whoever, please tell them to sign up ASAP. You know, we do think a lot about, we think a lot about that, but I think maybe that, like I said, like, I think the short answer is that we have a lot more to go. But we think of our ideal customers as people in external facing roles. So these are people who are typically doing performing activities, you know, sales activities or customer success activities or recruiting activities. And globally, that looks like, you know, 25% of the, typically, you know, about 25% of the headcount in a business is doing those activities. And if you say you have, you know, a billion knowledge workers globally.

AI assessment note: “We do not. We definitely do not have all of them.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q That's interesting right there. You broke it off, right? It reports, right?

A Exactly, exactly because I really felt that, like, first of all, I found personally, I think being a very successful field marketer has more to do with having very tight alignment with your regional sales director. I mean, that's the KPI for me is, are they happy with them? And the way I like our field marketers was to ask the regional sales director, have you worked with somebody you liked before? Cause that will make it successful. So like in some ways I did not have a lot to give there, right? Like it's not something I felt like it's so important for them. I want the sales or to choose them and like them and work with them. I will still give the content. I will still tell them how they eventually look like. But it's more important that they work closely together. Things are very regional. So in my mind, that belong with sales. It also works that way when you hire, like you hire X sales person in Y region, you get the field marketer. So like, put it there.

AI assessment note: “So in my mind, that belong with sales.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And then you realize like they work like, cause they're a touch. They are at You know, if you're doing them right. And so how, how do you, how did you measure it? Measure its contribution, that kind of stuff on the, on the quantify it.

A Yeah. I think because I came over to marketing from an engineer perspective, people really expected me to be like so obsessed with the numbers and not care about brand. When actually in reality, I kind of felt like the thing that will actually help me close deals is the brand side, like people hearing about us, hearing good things. First of all, I'll say that to this day, I'm involved in deals and I, you could sense it changing very easily over time. Like when I started, we would walk into a room and it was Cold, right? Like you would start from zero. You would have to be like, hi, I'm with, we're about security company. And then over time, you feel that the worms get, the room gets warmer, right? Now you walk into a room, it's warm, and your AEs feel it too. So there's also measurements that are not just numbers. But when it comes to numbers, I track a couple of things. First of all, my audience, My buyer, the budget at the end comes from CISOs, the, the senior executive that owns a security budget. They are a lot on LinkedIn. Like I trap how well we do on LinkedIn, how fast we grow. I need that exponential growth on LinkedIn. That's a good indication for me for brand because I can see the amount of buyers that Are subscribing to my content there. Then I have the other type of people, the people who actually use with like the, I mean, at the end, you'll have a CISO approve the…

AI assessment note: “when it comes to numbers, I track a couple of things.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q expert, but let's take it out a couple months, right? So you've got this data lock, right? But if my MCP is great, maybe I just grab those box files and that data, and I abstract away box. And sure, box has the data and the healthcare company. But if I can talk to it through a myriad of different levels and MCPs and everything, is it really a moat?

A I would actually argue that MCP is a thing that only enhances the underlying moat. Because data wants to be free. That doesn't mean that there's no moat around managing the data and making it useful. It wants to be incorporated in some other workflow. So for us, the more places where customers can use their data is only a net positive. We want to connect to every MCP, you know, environment that that's possible as a tool. And that just makes the continued feedback loop of having more data, at least in our environment, more valuable because, because you know that it's going to be accessible from all these other systems. So I think of that as kind of a, the analogy would be like, did APIs reduce people's modes? No, it actually in many cases made companies more sticky over time because they could be embedded into even more software, which made that even a greater level of, of sort of concentration. So, so I, I, I mean, I, I see no reason why MCPs wouldn't be just analogous to all of the, the APIs that we built over the past couple of decades.

AI assessment note: “I would actually argue that MCP is a thing that only enhances the underlying moat.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q at sales. They were so his top reps, his top reps. So one meta topic for snowflake is talking to your AI, right? Which you used to need to date. Maybe you still need a data scientist and a data engineer and the whole team, but tell us like. Versions of that story and where will, where's snowflake going in 20, 26 in this age of AI, where's it going?

A Yeah. I mean, first of all, Snowflay is the AI data cloud, meaning we basically want to be a cloud computing platform centered on data, whatever you want to do with it. Obviously there's simple stuff like analysis. You bring some data in. You want to make it easier for people to bring that data in. We're going to release a pile of new connectors. But then analytics is what we were always known for. Infinitely scalable analytics. Difficult. Everything from AML to predicting next best action, or as you pointed out, churn detection. But for us, AI is a big unlock as far as getting value from data goes. If we can make any business user be able to ask questions off of data quickly, that's a big plus. You just showed me your chatbot. On your website. It's pretty amazing. If you folks haven't tried it, you should. But now imagine being able to do that on every dataset that your company has. That's sort of, that's our thing. And the pieces to do that are already there. And the next steps then are going to be, okay, how do you stitch these data flows together? If you're a salesperson and you want to make a new pitch for a use case to your customer, you want to know perhaps like what are open use cases that other customers like this have deployed that this person should. You also want to make sure you know the latest about what's going on. How do you bring that into a single experience? …

AI assessment note: “That's kind of where Snowflake is headed, which is all of your enterprise data”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Absolutely. But I, but it happens every week I get an email like this. So how's it gonna change with AI?

A Look, the, the biggest change that's happening is that you have to do more to get your customers and prospects to pay attention to you. There's just an explosion of content. There's an explosion of emails. There's an explosion of outreach. And how are you going to cut through that noise? Not by, uh, first of all, if you have like egregiously wrong information, like Oh, your conference is next week. Then you're out. Like, you don't even get 10 seconds in that email, and you'll become a case study for what not to do. But then it becomes a, what does it actually take for a CEO like you to open that email and to engage? It better be exceptionally targeted. It better be personal, not personalized. We've been talking about personalization for a very long time, which is You segment your customers. You take your customers, and you personalize your data, and send it to everybody in that segment. That doesn't cut it anymore. It needs to be personal. It needs to be, Jason, here are the four posts that you did. Here is why I can help you with this single problem that you have, and let me get 10 minutes with you.

AI assessment note: “the biggest change that's happening is that you have to do more”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And I want, I've got a bunch of stuff I want to talk about, but when you said mandate for your team, cause this is a question we got even to Yaman yesterday. What does that mean? How do you show the team the path forward for AI and sales?

A It has to start with you as a leader. I'm in these tools constantly. I'm definitely the most well-versed in this area of the business. And I think I find a genuine curiosity. I'm interested in it. And also like I, I'm, I have such high conviction that this is going to be the most important thing that we can figure out in the next, uh, 12 to 24 months. And so anything that I'm doing, I'm putting into our leadership channels, my personal Clay workflows or the ChatGPT projects like that I use individually for me as a leader. And I take a lot of demos. I talked to a lot of founders. I listened to a lot of content to try to stay on the cutting edge with it, because like you said, it's changed radically in. Yeah. And the risk reward is so big that it takes up a lot of my mind share.

AI assessment note: “It has to start with you as a leader. I'm in these tools constantly.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q to do it out of the gate. So if it's, I hear you, you're the best of the best, but the next CRO I interview, I'm going to ask, how are you going to manage a team that's 25% AI and 75%? And if his answer is, I'm going to go, I'm going to find an AI guru, I think I'm going to tell the CEO not to hire him.

A That's a fair point. Yeah. And maybe it's semantics. There's a bunch of my personal workflows that are all, and we're saying anything AI is an agent now. I have a different definition of agent, but we don't need to get into. But yeah, a lot of my job is done through AI. So am I managing agents today? Sure, you could call it that. But I think the point remains, a lot of your job is going to be through AI workflows and agentic services and managing all of these tools. A lot of my job is managing the system and infrastructure of our business anyways. And so the same thing called by another name, I think the point is you need to be a highly systems engineering focused CRO to survive over the next two to five to 10 years. Yeah. If you don't have the acumen to be able to understand how customer journey connects to systems and infrastructure and connects to the rep process, And how this whole orchestration works, you will greatly struggle because you can't win on. Oh, I'm a great sales guy and I'm a good manager and people like me that I'm a good manager.

AI assessment note: “you need to be a highly systems engineering focused CRO to survive”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q migrated to the CIO. These are big decisions now, right? And the CIO, if I'm going to put more money into Google cloud, just generically, that's a CIO level decision. But if all the budgets go into AI, it's an interesting, it's not a tension, but it's a huge dynamic because so much budget It's going to AI, right? So I guess it's empowering the developers more in the org.

A It is, and I think, and I think they were empowered already with the cloud decisions. I do think they were weighing in a lot, and I think they were heavily weighing that, but it's, when it's a ten-year, five to ten-year contracting commitment, it just, it just gets bigger, and the influencers and the decision makers that are involved in that buying decision just balloons, versus AI is all, it's all experimental, and then yes, there's going to be the larger, bigger enterprise deals over time. We've got many of those too, but the developer usage is what's Teaching us what the future of this platform and our product set and our models and our infrastructure really needs to look like.

AI assessment note: “It is, and I think, and I think they were empowered already”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q question for you, having seen all of it with the sales team and the GTM team, like how do you get it just right? So you remain super customer centric, because if you're in sales, I might love to, I might Push a little too hard. Bring everything up for tomorrow, Sarah. How do you help the team manage that? Because it could be the better half a decade, right?

A Yeah. I honestly think we're playing the long game and I think the team fully appreciates that. And we think about our investment and time spent with customers as the payout doesn't happen immediately, nor should it, because they have to build trust. They also have to learn and we have to figure out what it is that we have to help support them with. To learn to then migrate. And so there's a ton of work we do right now that's around just training and how do we think about investing in their developer community within those companies? How are we educating them? How are we bringing them along on the journey? Because it's one thing to sell something to a CIO or a CTO, but it's a darn big another to go deep into the org and figure out how you actually get a lot of those developers. Many of them are certainly certified in using other cloud platforms if they're not already using Google. So It's a long game and it's actually something we talk about this a lot. You don't see this immediate return necessarily from investing in students, but it's the right thing for the future of where cloud and AI are going.

AI assessment note: “we think about our investment and time spent with customers as the payout doesn't happen immediately”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q the only thing anybody wants to talk about, but be a, be both objective, but a proponent. Why are you gaining share? But there's, you don't gain share at this scale, right? Unless there's two or three core reasons folks come in and they just pick, at least for more of their budget, if not a hundred, because we are in a heterogeneous world, but why are you gaining share?

A A lot of times, Jason, we have customers who will come in and move one workload over and we, because again, we started out with our core tenants of who Google Cloud is, we wanted to provide choice and we didn't want it to be this all or nothing. You have to move everything to Google on day one or not. And so a lot of what happened over the years is that, especially in the last three to four years, we won a lot of business just with single, mostly like modern app workloads. For example, people would come over and build a net new app on Google Cloud. Start to work with us and see how powerful actually that relationship was. And what you're now seeing in the last one to two years are all of those who three to four years ago took a bet on us and then have started to migrate more and more workloads over the like more recent, 18 to 24 months. And with AI, they're looking at it. We, we were the, we were the third place player for a long time in the cloud space, but we really are the first choice when it comes to AI. So now when all of those CIOs and CTOs had started to consider now, what do I do? They're getting pressure from your boards. Who is the player that actually can keep me the farthest ahead of the curve? Almost all of them came to us, whether they were already working with us for their cloud infrastructure, compute storage, etc. They came to us to actually ask the question f…

AI assessment note: “we won a lot of business just with single, mostly like modern app workloads”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Yeah. This one's the next one. Share the story. Fully commit to the process. Selling's highly distracting. Don't proceed unless you're all in. I do think you have to take baby steps to learn, right? There is a line, right? Where it's not that. One meeting is not a huge distraction, is it? But share your learnings here. Yeah.

A So just in fairness, this is size and this is size dependent, right? Some of what I will say is, When you've got a CEO that has a really good C-suite that's built out, and that CEO is, is not frontline selling, and they've got a fantastic COO and CFO, then it's easier to commit to a process, right? It's easier to spend time on the process. If you're in year three and you're still, it's still like founder-led sales, and you don't have your team built out as much, then the, then the cost of the distraction can be that much higher. But it's even like fundraising, is I see people taking one meeting, and then one fund says they're interested, but you never had any other funds involved, and that just takes on a life of its own. Yeah. Any process, think hard about whether you want to go, and if you do want to go, understand that it's going to take time. Some of the best fundraisers I've seen say, I'm going to effectively take three weeks off my business, and I'm going to raise this round. M&A, you've put so much time and effort into building your company, into putting this team together, energizing the team, you name it, every aspect of building, and yet you're going to half-ass your sales process, like arguably one of the most important things in your life, and I see it done. So I think the fact is, it's not just the founders that have to be fully committed and aligned and in agreeme…

AI assessment note: “this is size dependent, right? Some of what I will say is, When you've got a CEO”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Yeah, for sure. Okay. Manage team expectations. We probably hit this one before. It's as simple as manage their, don't let them start planning their new Tesla or beach homes or anything actually beyond that?

A It's a bit of many a slip between the cup and the lip, like this is a three percent, like just because we're going into play doesn't mean we'll get it done, doesn't mean we'll get it done now. And the default is you have a job at a company that is hopefully doing well. Again, if you've got a company that is not doing well, that is not growing, that is not meeting your expectations, your funder's expectations, your market expectations, then you've got a different situation on your hands. And in the context of this conversation, I guess it's not fair not to mention that side of the spectrum, but over there, probably the expectation to manage is this is going to be very hard to sell. This is going to be very hard to sell other than as an acqui-hire because we've taken a lot of money. We, unfortunately, we've made some mistakes and we don't deserve much more than that. So either way, being Open and honest and aligned with your top stakeholders can save you a tremendous amount of time.

AI assessment note: “just because we're going into play doesn't mean we'll get it done”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Just, you guys have been so analytic since day one, right? Yeah. Which if we have time, I'll, I'll touch on at the end, but at your scale at 250,000 customers, 1.2 billion, do you pretty much know how every quarter's gonna be and your job as CEO is next year, five, six quarters out? Like, do you sweat any given quarter anymore within, within, within a range?

A In a way, I would say there's some, some flexibility within the quarter. I think what's great about SaaS businesses and one of the reasons why, as a category, we enjoy a relatively high multiple is the predictability of the business. Once you go into a quarter, once you publish the results, you're already halfway into the quarter, and SaaS is a very predictable business. You have NR, you have your existing customer base in large numbers, how they're going to behave. So I think that's one of the great things about SaaS companies, and specifically for Monday, because of that, we have high Prediction ability into the quarter. And you can see a lot of SaaS companies when they give guidance, it's usually like they give a very narrow range in terms of revenue, sometimes even a few millions over a billion, which other industry can offer such prediction and guidance.

AI assessment note: “specifically for Monday, because of that, we have high Prediction ability into the quarter.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q told folks who are saying, oh, it's hard out there, it's gotten harder, I say to this that only some folks get it, go find your Monday. Go for it. Because Monday, like, it's always been an engine, and I want to talk about that in a minute, but any meta takeaways for folks on how you've been able to maintain that engine, right? Even as others have more variability.

A Um, yeah, so you mentioned a lot of kind of financial metrics, but I think it eventually it all boils down to the, your customer base, the product, uh, the expression, expansion potential. And I think maybe what's a little bit unique about Monday is the variety of customers, not just the, you know, total number of customers, which is relatively high over 250,000, but the variety across different industries, different markets, different countries, geographies. And I think this diversity in a way creates stability in a business because you're not overly exposed to one business sector for better or worse, right? I think a lot of companies who build specifically for tech enjoy the tech boom in, in, in, in, in, in, in, in, there's a flip side to that as well. So I think eventually companies who build for the actual industry or the some representation of the variety of businesses we have, how dare enjoy more stability over time. Yeah.

AI assessment note: “this diversity in a way creates stability in a business because you're not overly exposed”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q So I should know. So 2018, you start to go So two, like the GFC brings you into the commercial side from residential, and then, but you're 14 years in before you really go big, I'm all in on what we would call enterprise. And What was that accelerant? What was that? What created that big change?

A So we were being pulled into bigger and bigger companies. So the interesting thing about construction is very transient. So project manager, one company goes to work at another one, they bring Procore with them. And so we were getting pulled into bigger and bigger customers and we decided we were going to focus on one particular market. So we chose the Boston metropolitan market, which actually had some of the largest contractors there. And so we Myself and one of our salespeople, we just went knocking on doors and we finally found somebody who would let us in and and we basically We're able to show them the value of what we were able to provide. We clearly were not enterprise grade at the time. They knew that, but they basically worked with us. And then the thing about the construction industry is because it's so hyper local, if you think about it, if you're a construction company and you have a D a bulldozer, you're not going to work. 400 miles away. Cause how are you going to get that? 25 ton equipment over there because it's so local every there's a FOMO factor there. So the minute we got one, everyone else wanted to take a meeting with us. And so we just leveraged that. To get into all of the other ones. I mean, we get a pilot project and man, they would rake us over the coals and they would put us up in front of these committees of 50 people that were like judging our sof…

AI assessment note: “we were being pulled into bigger and bigger companies”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What, tell us what, what you're thinking, what you're working on and how did the customers think about it? Are they begging you for more AI? Do they want more automation, more work clothes? Do they want some part of Procore just to be easier to use because it's 20, 25? Like, how are you thinking about also how the customer, what are the customers asking for?

A All of what you just said, but it, by the way, it does start with ease of use. So forget about AI for a second. People need tools that they can actually use. So we invest a lot in our UX kind of investment front. But when it comes to data, what people are asking for is, first of all, our customers tell us that they can run 50% more construction volume on, uh, through their business if they're running on the Procore platform than if they're not. And why that matters is in the construction industry, it's a very low margin business, like two to three percent gross margin business. So you're talking about 80%, like imagine running that business, like a grocery store, it's very difficult, low margin. And so every Every time you can avoid hiring the next person, especially in a constrained market, like construction, there's not enough people to do the work. You actually have a competitive advantage. So first and foremost, they want to be, to increase the productivity of their workforce by leveraging technology. But that's usually starts with just managing workflows and capturing data and stuff like that, which is fine. But what the industry is waking up to realize is that, wait a minute. A lot of money is lost in construction because mistakes are made that shouldn't have been made because somebody didn't have the pattern recognition that they need. So now that they want to leverage t…

AI assessment note: “All of what you just said, but it, by the way, it does start with ease of use.”

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