The Exchanges

Q Um, why did you decide to not move away, but add mid-market and enterprise to the pretty purely SMB HubSpot?

A You know, that's a great question. I'll tell you then, um, when I joined HubSpot, this is January, 2020, uh, I looked at how we were running the company, how we were running marketing sales and service, and we were running HubSpot on HubSpot. And guess what? At that time, we were a 4500 person company. So well out of our target segment zone and our ICP. And it was working beautifully. I could get all the reports. I could get all the insights. I didn't have to ask anybody. It was right there. And we were customer number zero for HubSpot. So product was absolutely ready. Then the question is, you know, can you get the partner ecosystem? Can you get the whole company behind moving up market? And just so we, we know, we're talking about two to 2000. We're not talking about 20,000 person company. We're not talking about 200,000 person company. We're still talking The segment that we were originally focused in, which is two to 2000, but the opportunity to go to a thousand person company and help them grow across marketing, sales, and service was huge. Our product was already there, and so the next step was to state that as part of the strategy and to get the whole company behind serving an upmarket customer in that space, and It's worked out.

AI assessment note: “Our product was already there, and so the next step was to state that”

Q I was like, my word, that is the title of a podcast. What do you mean by AI is history's greatest equalizer for SMBs?

A 50% of companies that get started fail within the first five years. And starting is hard. Starting a company is really hard. You know this. But scaling a company is absolutely brutal, right? And if you think about why is scaling so hard, especially for small, medium businesses, they operate under constraints, and particularly three constraints. They are headcount constrained. They cannot add the next headcount. They are capital constrained. They don't have big budgets. And they are expertise constrained. They don't have an army of consultants and resources to kind of like bank upon. So, uh, they operate under constraints, but yet have grand ambitions. And when I said that AI is a, you know, equalizer, uh, for SMBs, it removes each one of those constraints. So think about headcount. You know, if you're using AI for support, You may not need to hire the next support person for a bit longer, right? So I think it does unblock the headcount constraint. Think about it for marketing. You know, if you have, like, a huge budget, then you can personalize every single message that you send out, but if you don't have a huge budget, you're not going to be able to do that, but now AI can help you look at your ICPs, look at segments, not as broad segments, but as individual You know, customers that you want to be able to prospect and, you know, get much better conversion rates. So no need for…

AI assessment note: “when I said that AI is a, you know, equalizer, uh, for SMBs, it removes each one of those constraints.”

Q What signals do you think we're seeing that are most exciting?

A Look, I think, um, support is a very clear signal. We have agents, you know, that customer agent that we have, we have 1500 customers, and within weeks we saw 42 to 45% of tickets being deflected by AI. And that's a handful of weeks, right? Internally, we've been using AI to resolve tickets, 35% in year one, and now we'll be on to 50%. So, Very, very clear signal in terms of leveraging AI in order to scale support. I would say the same thing in terms of marketing. We've used marketing to drive conversion by having more personalized emails. That has, you know, driven conversion rates, and that has helped us, like, scale marketing, and so it's, ah, early, but at this point in the technology, we're looking for signals.

AI assessment note: “support is a very clear signal. We have agents... 42 to 45% of tickets being deflected”

Q I was like, my word, that is the title of a podcast. What do you mean by AI is history's greatest equalizer for SMBs?

A 50% of companies that get started fail within the first five years. And starting is hard. Starting a company is really hard. You know this. But scaling a company is absolutely brutal, right? And if you think about why is scaling so hard, especially for small, medium businesses, they operate under constraints, and particularly three constraints. They are headcount constrained. They cannot add the next headcount. They are capital constrained. They don't have big budgets. And they are expertise constrained. They don't have an army of consultants and resources to kind of like bank upon. So, uh, they operate under constraints, but yet have grand ambitions. And when I said that AI is a, you know, equalizer, uh, for SMBs, it removes each one of those constraints. So think about headcount. You know, if you're using AI for support, You may not need to hire the next support person for a bit longer, right? So I think it does unblock the headcount constraint. Think about it for marketing. You know, if you have, like, a huge budget, then you can personalize every single message that you send out, but if you don't have a huge budget, you're not going to be able to do that, but now AI can help you look at your ICPs, look at segments, not as broad segments, but as individual You know, customers that you want to be able to prospect and, you know, get much better conversion rates. So no need for…

AI assessment note: “when I said that AI is a, you know, equalizer... it removes each one of those constraints.”

Q Um, why did you decide to not move away, but add mid-market and enterprise to the pretty purely SMB HubSpot?

A You know, that's a great question. I'll tell you then, um, when I joined HubSpot, this is January, 2020, uh, I looked at how we were running the company, how we were running marketing sales and service, and we were running HubSpot on HubSpot. And guess what? At that time, we were a 4500 person company. So well out of our target segment zone and our ICP. And it was working beautifully. I could get all the reports. I could get all the insights. I didn't have to ask anybody. It was right there. And we were customer number zero for HubSpot. So product was absolutely ready. Then the question is, you know, can you get the partner ecosystem? Can you get the whole company behind moving up market? And just so we, we know, we're talking about two to 2000. We're not talking about 20,000 person company. We're not talking about 200,000 person company. We're still talking The segment that we were originally focused in, which is two to 2000, but the opportunity to go to a thousand person company and help them grow across marketing, sales, and service was huge. Our product was already there, and so the next step was to state that as part of the strategy and to get the whole company behind serving an upmarket customer in that space, and It's worked out.

AI assessment note: “we were running HubSpot on HubSpot... So product was absolutely ready.”

Q What signals do you think we're seeing that are most exciting?

A Look, I think, um, support is a very clear signal. We have agents, you know, that customer agent that we have, we have 1500 customers, and within weeks we saw 42 to 45% of tickets being deflected by AI. And that's a handful of weeks, right? Internally, we've been using AI to resolve tickets, 35% in year one, and now we'll be on to 50%. So, Very, very clear signal in terms of leveraging AI in order to scale support. I would say the same thing in terms of marketing. We've used marketing to drive conversion by having more personalized emails. That has, you know, driven conversion rates, and that has helped us, like, scale marketing, and so it's, ah, early, but at this point in the technology, we're looking for signals.

AI assessment note: “Look, I think, um, support is a very clear signal.”

Q That is fantastic. I want to start with the movement into the role of CEO. It's a thirty one billion dollar public company. I mean, the size of HubSpot is incredible. The question that I want to start with is, the founders are still fairly involved. What's it like being CEO where the founders are still fairly involved?

A It is a privilege and honor, uh, to take over from a founder, and it's hard and tough work to make it work. I think for me, um, I'd been at the company for about a year, and I always looked at, like, the decisions that Brian and Dharmesh made in starting and scaling the company. Deep conviction in SMB. Deep conviction in building a platform and crafting the platform Deep conviction in having culture as a product. Like, those are decisions that I just loved, and I completely believed in. So I think that is the easier part, and that's the pro of working with founders who have, who know the company, who have taken it from very small, you know, startup to scaling it to a public company and beyond. Um, I think on the flip side, it's a lot of work. You know, when the transition happens, you have to think about a lot of things during the transition and throughout, you know, after. What's the cadence? Do you want to send 20 emails a day or two emails? And what's the altitude? Do you want to talk about the strategy and the product, or do you want to talk about the whole business? And if it's one or the other, you really need to make sure that you're covering the bases across all of those conversations. And then what do you do when something Bad happens, which something will happen, right? If you hit a pothole, or if you make a bet that does not work, what happens? How are you gonna, lik…

AI assessment note: “It is a privilege and honor, uh, to take over from a founder”

Q Is it not an entirely different company that you've got to build?

A No, I don't think it is that, uh, you know, different, especially if you think about how we went about doing it is we were already serving You know, companies with 200 employees, and then we started serving companies with 500 employees, and then we started serving companies with thousands. So I think, like, there is a, uh, myth that, you know, there's a completely different motion, and you gotta, like, go and hire all these enterprise class, you know, reps to come and sell, and in fact, if you do that, that will break the system, and that will break the culture. But if you think about, uh, more incremental approach of, Getting the product to be perfect fit for the next higher segment. So going from 200 to 500. And then looking at the kind of sales and support organization that you need and up leveling them incrementally the next year to make sure that they can serve a 500 person company and then taking it up to thousand and taking it up to 2000. That is a much better way of scaling up market. And we've been able to Bring along our reps by upscaling them. We've been able to bring along our partner ecosystem by upscaling them. We've been able to continuously drive innovation in the product as we go upmarket.

AI assessment note: “No, I don't think it is that, uh, you know, different”

Q Ah, that's why I'm single. Now I get it. You said about the deep conviction there across, I mean, it's amazing when you look at the deep conviction to, as you said, SMB, the GCM, doing CRM at all from nothing when it was such a mature space. Are you able to have such deep conviction as a public company CEO when the street does react very strongly to decisions?

A Yeah, you have to have deep conviction in order to run a public company, and if those decisions and the choices that you make are counterintuitive, Even better, right? And it's almost like you got to forget that you're a public company and you got to start with the basics of what do you believe in? One of the things that I just came from talking to investors this whole day, we had a whole non-deal roadshow today. We spent a lot of time talking to investors. They actually appreciate your conviction in your business. That's what they like to hear. And so when we, you know, talk to them about why we make These decisions, why we focus on the segments that we do, they get our story.

AI assessment note: “Yeah, you have to have deep conviction in order to run a public company”

Q What did you have to get comfortable that you weren't comfortable doing before?

A Look, one of the biggest changes when you go from any, you know, position into a CEO, the number of stakeholders that you have is massive. You now have the board, you have investors, you have founders, and you have like a broader employee population across a lot of teams, and so it's like the number of key stakeholders that judge you, that focus on what you're doing, and Uh, look at you. It's just broad, right? So that's number one. What I got comfortable with is that no matter how hard I try, I'm not going to perfectly hit the approval of all of those stakeholders. At some point, I'm going to do something which, you know, is super beneficial to customers. At some point, I'm going to do something that employees are happy about. At some point, I'm going to do something that board members are satisfied with and maybe investors are not. So you're never going to hit that perfect equilibrium where you're Satisfying and maybe even overachieving the expectations of all of your stakeholders. So then how do you make decisions? Well, that's the job.

AI assessment note: “What I got comfortable with is that no matter how hard I try, I'm not”

Q What do you think is the most counterintuitive decision that HubSpot is making today that may not be obvious?

A A couple of things come to mind. Um, I would say pricing, and we'll talk about AI pricing, but When AI came on the scene in 20, 22, November, we fairly immediately moved into products, you know, product building, and we changed our roadmap. We actually stopped our roadmap, changed the roadmap, and started building product. And since that day, they're like, how are you going to monetize it? You know, what are you going to do with monetization? And we have a deep conviction that there's one product, which is an AI product, and it's going to be inbuilt into every hub and every part of the platform. And that means Monetization is the entire platform, and Harry, I can't tell you, every day I get asked this question about 10 times, how are you monetizing it? We're monetizing it with the current product, and that's how we plan to build, and I think it is a, it's counterintuitive because today everybody has an AI SKU, they slap a premium on the SKU, or they put a, you know, usage metric, or they put an outcome metric, and there's just a lot of swirl about how you price products, but I think the first thing that you got to do when a big Tech shift like this happens is to focus on customer value.

AI assessment note: “it's counterintuitive because today everybody has an AI SKU, they slap a premium”

Q What's slapping on and what's doing it the right way?

A Well, I think, um, think about this from an end user perspective. When A product is kind of like neat and novel. They're going to use it for one day, and then they're probably going to check it out again once every two weeks, or maybe they're not going to, and then they churn out. So it's really the difference between neat and necessary, and necessary means you're using it every single day. You cannot get your job done without it, and so the best way to think about leveraging AI and building it into your product is Can that feature go from neat to necessary? And can it become like essential as part of the workflow of your end user that they cannot live without it, right? That's the thing that we have to do, and you can't get it. It's not a slam dunk. You can't just like launch an AI feature next day. You know, it's like millions of users. There's a lot of iterative work that needs to happen to figure out Which, you know, features are going to go from neat to necessary and that's the way to think about building it into the product rather than slapping one feature and then.

AI assessment note: “It's really the difference between neat and necessary”

Q So what do you believe that most around you disbelieve?

A Pricing strategy should not be to chase revenue, but it should be to attract revenue. Most people think that pricing is a way to maximize revenue, and that's why you get all these questions of AI, how are you going to monetize it, and what's the, the next big thing that you're going to do? We always look at how do we provide value for customers first, and we've consistently actually lowered pricing, To increase the value that we provide and the compelling value that we provide attracts more customers. A lot of people think that, you know, pricing is to maximize every dollar and therefore, you know, get to revenue maximization. We actually think about it as market share maximization, which means you'll approach pricing very differently.

AI assessment note: “Pricing strategy should not be to chase revenue, but it should be to attract revenue.”

Q Ah, that's why I'm single. Now I get it. You said about the deep conviction there across, I mean, it's amazing when you look at the deep conviction to, as you said, SMB, the GCM, doing CRM at all from nothing when it was such a mature space. Are you able to have such deep conviction as a public company CEO when the street does react very strongly to decisions?

A Yeah, you have to have deep conviction in order to run a public company, and if those decisions and the choices that you make are counterintuitive, Even better, right? And it's almost like you got to forget that you're a public company and you got to start with the basics of what do you believe in? One of the things that I just came from talking to investors this whole day, we had a whole non-deal roadshow today. We spent a lot of time talking to investors. They actually appreciate your conviction in your business. That's what they like to hear. And so when we, you know, talk to them about why we make These decisions, why we focus on the segments that we do, they get our story.

AI assessment note: “Yeah, you have to have deep conviction in order to run a public company”

Q How do you, like, do you think from a downside protection mindset, from an upside maximization mindset, from a, how do you think about that decision making then when you have so many different stakeholders?

A I, I think you have to have, again, uh, some very strong North Stars, right? Like, what are you optimizing for? And within HubSpot, we've said solve for the customer, SFTC, and solving for the customer is the North Star. So, if there is, you know, ever, you know, kind of a decision between are we solving for the company or the customer, it's always the, you know, customer. And there's something that we say, it's like, Customer over company, over team, over self. And that is a guiding framework and a principle, which means when in doubt, always do the right thing for the customer, then for the company, and you shouldn't be solving for yourself, right? And so I think, like, there are guiding principles in terms of how you think about decisions, which will, you know, shift it one way or the other, but you're still not going to get every one of those decisions right.

AI assessment note: “Customer over company, over team, over self. And that is a guiding framework”

Q Is it not an entirely different company that you've got to build?

A No, I don't think it is that, uh, you know, different, especially if you think about how we went about doing it is we were already serving You know, companies with 200 employees, and then we started serving companies with 500 employees, and then we started serving companies with thousands. So I think, like, there is a, uh, myth that, you know, there's a completely different motion, and you gotta, like, go and hire all these enterprise class, you know, reps to come and sell, and in fact, if you do that, that will break the system, and that will break the culture. But if you think about, uh, more incremental approach of, Getting the product to be perfect fit for the next higher segment. So going from 200 to 500. And then looking at the kind of sales and support organization that you need and up leveling them incrementally the next year to make sure that they can serve a 500 person company and then taking it up to thousand and taking it up to 2000. That is a much better way of scaling up market. And we've been able to Bring along our reps by upscaling them. We've been able to bring along our partner ecosystem by upscaling them. We've been able to continuously drive innovation in the product as we go upmarket.

AI assessment note: “No, I don't think it is that, uh, you know, different”

Q What do you think is the most counterintuitive decision that HubSpot is making today that may not be obvious?

A A couple of things come to mind. Um, I would say pricing, and we'll talk about AI pricing, but When AI came on the scene in 20, 22, November, we fairly immediately moved into products, you know, product building, and we changed our roadmap. We actually stopped our roadmap, changed the roadmap, and started building product. And since that day, they're like, how are you going to monetize it? You know, what are you going to do with monetization? And we have a deep conviction that there's one product, which is an AI product, and it's going to be inbuilt into every hub and every part of the platform. And that means Monetization is the entire platform, and Harry, I can't tell you, every day I get asked this question about 10 times, how are you monetizing it? We're monetizing it with the current product, and that's how we plan to build, and I think it is a, it's counterintuitive because today everybody has an AI SKU, they slap a premium on the SKU, or they put a, you know, usage metric, or they put an outcome metric, and there's just a lot of swirl about how you price products, but I think the first thing that you got to do when a big Tech shift like this happens is to focus on customer value.

AI assessment note: “I would say pricing... it's counterintuitive because today everybody has an AI SKU”

Q What did you have to get comfortable that you weren't comfortable doing before?

A Look, one of the biggest changes when you go from any, you know, position into a CEO, the number of stakeholders that you have is massive. You now have the board, you have investors, you have founders, and you have like a broader employee population across a lot of teams, and so it's like the number of key stakeholders that judge you, that focus on what you're doing, and Uh, look at you. It's just broad, right? So that's number one. What I got comfortable with is that no matter how hard I try, I'm not going to perfectly hit the approval of all of those stakeholders. At some point, I'm going to do something which, you know, is super beneficial to customers. At some point, I'm going to do something that employees are happy about. At some point, I'm going to do something that board members are satisfied with and maybe investors are not. So you're never going to hit that perfect equilibrium where you're Satisfying and maybe even overachieving the expectations of all of your stakeholders. So then how do you make decisions? Well, that's the job.

AI assessment note: “What I got comfortable with is that no matter how hard I try”

Q What's slapping on and what's doing it the right way?

A Well, I think, um, think about this from an end user perspective. When A product is kind of like neat and novel. They're going to use it for one day, and then they're probably going to check it out again once every two weeks, or maybe they're not going to, and then they churn out. So it's really the difference between neat and necessary, and necessary means you're using it every single day. You cannot get your job done without it, and so the best way to think about leveraging AI and building it into your product is Can that feature go from neat to necessary? And can it become like essential as part of the workflow of your end user that they cannot live without it, right? That's the thing that we have to do, and you can't get it. It's not a slam dunk. You can't just like launch an AI feature next day. You know, it's like millions of users. There's a lot of iterative work that needs to happen to figure out Which, you know, features are going to go from neat to necessary and that's the way to think about building it into the product rather than slapping one feature and then.

AI assessment note: “it's really the difference between neat and necessary”

Q That is more expensive than just running traditional HubSpot, no?

A Yeah, I, I don't think the, first of all, model costs and cost of inferences come down pretty significantly. You know, you look at it in 2023 to where we are now, it's come down significantly. I think cost curve is going to continue to, you know, decline. I wish we had a margin problem. That means the usage is going to be really high. I think we're still in the early parts of Getting the features out, getting people to use it on a daily basis. So I don't think that there is margin degradation. Um, and I, I continue to believe that the cost of inference is going to continue to come down, that we won't see that. There'll be a lot more value that we can generate for our customers.

AI assessment note: “So I don't think that there is margin degradation.”

Q So what do you believe that most around you disbelieve?

A Pricing strategy should not be to chase revenue, but it should be to attract revenue. Most people think that pricing is a way to maximize revenue, and that's why you get all these questions of AI, how are you going to monetize it, and what's the, the next big thing that you're going to do? We always look at how do we provide value for customers first, and we've consistently actually lowered pricing, To increase the value that we provide and the compelling value that we provide attracts more customers. A lot of people think that, you know, pricing is to maximize every dollar and therefore, you know, get to revenue maximization. We actually think about it as market share maximization, which means you'll approach pricing very differently.

AI assessment note: “Pricing strategy should not be to chase revenue, but it should be to attract revenue.”

Q To what extent does it sometimes feel like that versus do you believe the other belief, which is like, hey, resource allocation is the sole job of a CEO or the main job of a CEO?

A Uh, politician. No, I don't want to be a politician, and no, I don't think, think of my job. I think I would like not do this job if I had to Be very political. In fact, I want none of politics or none of those considerations in terms of how we make decisions. You know, I took on this role as a CEO for HubSpot because I think we can, you know, we have such a big opportunity. The mission of what we are trying to do, which is to help small and medium businesses grow, is just so personal to me, and it's so motivating and inspiring that that is the focus for me. And, you know, How, how do you make, you know, decisions on a given day? How do you pivot? That you said it comes from resource allocation. I actually think about it as resource alignment. You know, what I mean by that is, you know, have you heard this term that, ah, culture eats strategy for breakfast? You know, I, I said this to our team, alignment eats strategy for lunch. And what I mean by that is the biggest job You know, job number one is setting up strategy, but I think what is even more important and critical in terms of a CEO is aligning all of the resources to accomplish that strategy. And as teams grow, and as they get, like, distributed, as they get, like, much bigger, vectors are totally not aligned.

AI assessment note: “I actually think about it as resource alignment.”

Q To what extent does it sometimes feel like that versus do you believe the other belief, which is like, hey, resource allocation is the sole job of a CEO or the main job of a CEO?

A Uh, politician. No, I don't want to be a politician, and no, I don't think, think of my job. I think I would like not do this job if I had to Be very political. In fact, I want none of politics or none of those considerations in terms of how we make decisions. You know, I took on this role as a CEO for HubSpot because I think we can, you know, we have such a big opportunity. The mission of what we are trying to do, which is to help small and medium businesses grow, is just so personal to me, and it's so motivating and inspiring that that is the focus for me. And, you know, How, how do you make, you know, decisions on a given day? How do you pivot? That you said it comes from resource allocation. I actually think about it as resource alignment. You know, what I mean by that is, you know, have you heard this term that, ah, culture eats strategy for breakfast? You know, I, I said this to our team, alignment eats strategy for lunch. And what I mean by that is the biggest job You know, job number one is setting up strategy, but I think what is even more important and critical in terms of a CEO is aligning all of the resources to accomplish that strategy. And as teams grow, and as they get, like, distributed, as they get, like, much bigger, vectors are totally not aligned.

AI assessment note: “I actually think about it as resource alignment... aligning all of the resources to accomplish that strategy.”

Q When we think about the movement up to a higher employee base, um, you do more and more nudge into Salesforce's territory. You've always, not you, but like HubSpot's always been quite like, yeah, no, we're not really, we're not really competitors, no, no, no. And they're always like, no, no, no, they're not competitors. Um, it's like, You kind of are, right?

A Look, it's a, it's a, it's a very large market. And, uh, B to B apps are not winner take all markets. It's different than consumer apps. You know, consumer apps, you, you, you see one use case. There's a, there's an app that comes in and then it's like 90% of the market is just like one provider. Uh, that's not been the case. Almost any of B to B apps, whether you look at like HR or finance or recruiting or, you know, you look at like CRM, they all have multiple players. And I think the way we look at it is for the two to 2000 segment, You know, we have a great product, and we have a great go-to-market fit, and so we're really good at that, and then, you know, Salesforce has got, like, this amazing, you know, enterprise segment that they're really good at, and so, yes, is there an overlap, you know, in the upper end of our upmarket, you know, a two-thousand-person company? Sure, we see them, and, you know, they probably are like, yeah, we have a whole space in, uh, enterprise, and okay, there's some overlap there, so yeah, are we, You know, competitive in one portion of the segment, yes, but we also focus on really delivering for that entire, you know, SMB, which is the two to 2000 space we've been talking about.

AI assessment note: “are we, You know, competitive in one portion of the segment, yes”

Q How do you, like, do you think from a downside protection mindset, from an upside maximization mindset, from a, how do you think about that decision making then when you have so many different stakeholders?

A I, I think you have to have, again, uh, some very strong North Stars, right? Like, what are you optimizing for? And within HubSpot, we've said solve for the customer, SFTC, and solving for the customer is the North Star. So, if there is, you know, ever, you know, kind of a decision between are we solving for the company or the customer, it's always the, you know, customer. And there's something that we say, it's like, Customer over company, over team, over self. And that is a guiding framework and a principle, which means when in doubt, always do the right thing for the customer, then for the company, and you shouldn't be solving for yourself, right? And so I think, like, there are guiding principles in terms of how you think about decisions, which will, you know, shift it one way or the other, but you're still not going to get every one of those decisions right.

AI assessment note: “Customer over company, over team, over self. And that is a guiding framework”

Q That is more expensive than just running traditional HubSpot, no?

A Yeah, I, I don't think the, first of all, model costs and cost of inferences come down pretty significantly. You know, you look at it in 2023 to where we are now, it's come down significantly. I think cost curve is going to continue to, you know, decline. I wish we had a margin problem. That means the usage is going to be really high. I think we're still in the early parts of Getting the features out, getting people to use it on a daily basis. So I don't think that there is margin degradation. Um, and I, I continue to believe that the cost of inference is going to continue to come down, that we won't see that. There'll be a lot more value that we can generate for our customers.

AI assessment note: “So I don't think that there is margin degradation.”

Q When we think about the movement up to a higher employee base, um, you do more and more nudge into Salesforce's territory. You've always, not you, but like HubSpot's always been quite like, yeah, no, we're not really, we're not really competitors, no, no, no. And they're always like, no, no, no, they're not competitors. Um, it's like, You kind of are, right?

A Look, it's a, it's a, it's a very large market. And, uh, B to B apps are not winner take all markets. It's different than consumer apps. You know, consumer apps, you, you, you see one use case. There's a, there's an app that comes in and then it's like 90% of the market is just like one provider. Uh, that's not been the case. Almost any of B to B apps, whether you look at like HR or finance or recruiting or, you know, you look at like CRM, they all have multiple players. And I think the way we look at it is for the two to 2000 segment, You know, we have a great product, and we have a great go-to-market fit, and so we're really good at that, and then, you know, Salesforce has got, like, this amazing, you know, enterprise segment that they're really good at, and so, yes, is there an overlap, you know, in the upper end of our upmarket, you know, a two-thousand-person company? Sure, we see them, and, you know, they probably are like, yeah, we have a whole space in, uh, enterprise, and okay, there's some overlap there, so yeah, are we, You know, competitive in one portion of the segment, yes, but we also focus on really delivering for that entire, you know, SMB, which is the two to 2000 space we've been talking about.

AI assessment note: “are we, You know, competitive in one portion of the segment, yes”

Q That's a shit question, isn't it? Who would ask that? Right?

A Right? The number of times- Editors take it out. The number of times I get asked that question, so there's a bit of a myth that the only way to grow, the only way to serve millions of customers, the only way to You know, become a very large, you know, company is by going up market. And I wished, you know, someone would ask, why do you have deep conviction in mid market? And we would say, look, there is an enterprise market that's very large. There's a market for SMBs. We want to define a category of mid market software. And, you know, five years from now, 10 years from now, when you have guests in your podcast, I want you to ask them, hey, are you like Salesforce? Are you like HubSpot serving mid market? Or are you like Intuit serving SMB? And That is a question that I'd love to dig into.

AI assessment note: “The number of times I get asked that question”

Q Um, I'm gonna go there, why not? Uh, unlimited vacation, uh, mental health days, uh, no meeting Fridays, or is this just, like, signs of woke times, or is this, like, a part of culture?

A Hey, that, so we just actually made a change from unlimited vacation times to flexible time off. And, ah, that is, you know, something that we have, like, moved the culture around. Now, a lot of what you talked about happened in twenty-twenty, twenty-twenty-one, and those were times that, you know, as a humanity, we were going through pandemic for the first time, and people were losing their lives, livelihoods, and parents were trying to figure out how to work from home, and so I think, It was a time where there was support that was necessary. I think we've, we've now really refocused the company in terms of customer outcomes, mission orientation. We just made this, you know, change into flexible time off. Don't ask me how it goes.

AI assessment note: “we just actually made a change from unlimited vacation times to flexible time off”

Q Where does it feel most different? You know, when you go from 200 to 400, and then 400 to 800, and then 800 to 15. Where's that like, oof, this is different to the last phase.

A When the complexity of the buying process on behalf of the customer goes from I'm making decisions, I got the budget, to I have a committee of people that now need to make the decisions, that includes IT, that includes procurement, that includes security, that includes our maybe the board, then it gets diff, not different, It probably gets a little bit more different, and that's where we had to, like, upskill our sales team. How do you sell to a committee versus an individual owner or a sole proprietor or a VP of marketing? How do you make sure that you're driving a process that makes sense, that works for customers upmarket, right? So I think there is a, uh, organic way of upskilling that you can do to You know, make sure that your team is enrolled in the process, the skills are getting better, and then, you know, you begin to set that flywheel in motion.

AI assessment note: “When the complexity of the buying process on behalf of the customer goes from”