Cold open
When you are in a wartime or a hard time, you are optimizing for speed of execution. When you are in peacetime, you are optimizing for getting a consensus around what you’re trying to do. You got to be good at both and many other modes of operating. B2B apps are not winner take all markets. Whether you look at HR, finance, CRM, they all have multiple players. The best competitors make you better. And I think Salesforce does a really good
job of This is 20 VC
Intro
with me, Stebbings, and today we focus on HubSpot. HubSpot is one of the category defining companies of our time. Before HubSpot, no one believed that you could build a monster business focused on SMBs. No one also believed that you could come in and compete with Salesforce in the most competitive software space of all, CRM. Well, they did both, and now they have a market cap of $31,000,000,000 and revenues of 2,600,000,000. Joining me today, we have HubSpot CEO, Yamini Rangan, who joined us in the studio in London.
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Conversation
Yeah, Yamini. Listen, I spoke to Brian, I spoke to Pat, I spoke to Jay Simons, Claire Hughes Johnson. I mean, I think I stalked the shit out of you bluntly before No, this god. I know, terrifying, but thank you so much for joining me.
Thank you for having me, Harry. It’s been a long time. I’ve been long time listener, first time talker to you there.
That is fantastic. I wanna start with the movement into the role of CEO. It’s a $31,000,000,000 public company. I mean, the size of HubSpot is incredible. The question that I wanna start with is, the founders are still fairly involved. Yep. What’s it like being CEO where the founders are still fairly involved?
It is a privilege and honor to take over from a founder. And it’s hard and tough work to make it work. I think for me, I’d been at the company for about a year. 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. Those are decisions that I loved and I completely believed in. So I think that is the easier part and that’s the pro of working with founders who know the company, who have taken it from very small start up to scaling it to a public company and beyond.
I think on the flip side, it’s a lot of work. When the transition happens, you have to think about a lot of things during the transition and throughout 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 like make it work, right? So there’s a lot of work that you need to put in. And just like any relationship that you have, right? First of all, you have to commit to it. And then you got to put the work in order to make it function. And so, there’s a lot of work.
That’s why I’m single. That’s just now I get it. You said about the deep conviction there across 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?
Yeah. You have to have deep conviction in order to run a public company. If those decisions and the choices that you make are counterintuitive, even better. You’ve got to forget that you’re a public company and you’ve 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.
What do you think is the most counterintuitive decision that HubSpot is making today that may not be obvious?
A couple of things come to mind. I would say pricing. When AI came on the scene in twenty twenty two 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 gonna monetize it? You know, What are you gonna do with monetization? And we have a deep conviction that there’s one product, which is an AI product. 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 that SKU or they put a 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 gotta do when a big tech shift like this happens is to focus on customer value.
I’m a fan of making bold statements unsupported by data, because I’m a venture capitalist. So when you look at outcome based pricing, it is impossible, unless it is completely non human in the loop. Because otherwise, there’s always gonna be this continuous debate, well, actually Yamini, I did 80% of the sale and your agent only did 20%, so I don’t wanna pay a 100% for your outcome.
How
do you think about how quickly we’ll be able to move to outcome based pricing and whether that even is the solution for a next generation of AI?
There’s a lot of swirl, isn’t there?
Yeah.
I mean, I think there’s a lot of swirl on, is it seats? Are seats going to completely go away? Is it outcome? Is it some form of consumption credit?
But also, you’re a horizontal based product like HubSpot is, you have some customers that will use you for LPs, like I will do for fun. That’s very Versus high a florist, which is a very low ticket. And so you can’t just have the same outcome based pricing.
Yeah. We believe that in the fullness of time, we will have hybrid pricing. We’ll have some seed based pricing and some usage based pricing. I think it’s really hard to think about outcomes for exactly the same reason that you’re talking about, right? Which is, how can you validate an outcome? And especially if you offer a platform, which on one spot can resolve a ticket, on the other can help you set up a meeting, on the other, write a blog or a social post for you. The outcomes are so different.
How are you going to validate all of it? The simpler way, at least for SMB, our customer base, to think about it is results. And it’s more of usage. Are you using a certain credit? Are you using something in our AI platform? It’s a credit based mechanism rather than an outcome based mechanism. So that’s how I think it’s going to evolve.
I do want to go back and just before we move to the leadership element where we mentioned obviously the transition to some elements hard, some elements easier. Yeah. Can you describe one thing that I thought was just brilliant question. I can’t say who it was from, but it was great. Describe one thing you’ve changed at HubSpot culturally or strategically since becoming CEO that might not have happened under Brian?
Look, I think we are going from a scale up to a grown up stage. And one of the things at HubSpot that I heard when I took on is that we don’t like process. Process is a four letter bad word. We don’t wanna talk about process. And you need a certain amount of process as you grow and you become a bigger company, distributed company across multiple offices. So, one of the things that I’ve done is really focused on tying strategy to priorities to outcome. And when you run a large grown up company, the clarity of what is important is really needed.
So, strategy is just that. What’s the most important work that we do as an organization? Then the second part of it is priority. Off that strategy, what are you going to do this year? That’s a priority. And then the third part of it is what do you commit as outcomes based on the work that you’re doing this year, and are you accountable for that outcome? And the strategy to priority to outcome is something that I’ve obsessed about for the last couple of years.
Just so I get an example So of what strategy
the strategy is threefold, Harry. Super simple. Focus and obsess on our customer. Everything starts with the customer. Second, make our product easy, fast, and unified. And third is have a growth mindset and become grow getters ourselves. That structure of going from strategy to priorities to outcome is something that you need as you scale and you become even bigger and distributed. I can’t see Brian is awesome. He probably would have done a lot of things. I don’t know if you would have put a framework like process that we have driven.
Can I ask you, online is the have a growth mindset? Always think you want something where someone can take the alternate side. Yeah. So for example, for me, I believe working unreasonably hard yields better outcomes. There you go. Work life balance is a complete myth.
Yes.
But many people disagree with me and that’s fine. Yeah. But you take the four or against. No one wants someone who doesn’t have a growth mindset, do they?
That is not true. I’ll push you on that. Go on. I mean, people love the comfort of what they have done every single day. Look at AI, which is coming, you know, and one of the things that we’re talking to the whole company about is can we become AI first ourselves? Can we learn how to do proms? Can we start using AI every single day? Well, the answer is not everybody wants to do that, because they’re comfortable. Some of us are comfortable doing whatever we’ve been doing for, you know, the last decade.
And so I think growth mindset, the alternate is comfort in how you do what you do, and maybe even comfort in the expert level that you have based on what you have done for a long period of time. Asking questions, being curious, learning, adapting, that is not a given in any company, or that’s not even a given in the mindset. And I think the larger you become, you do have people who like the comfort of, I’ve done this before and I’ve done it a certain way.
I know how to do it and I’m very comfortable doing it the way that I have done it before.
I totally agree with you and I think that’s absolutely fair. I think I probably just don’t like those people.
But you’re
right. That is, you know, I’m sure a large portion of large company workforces. Can I ask what were you comfortable in how you did that you’ve had to change? Was it leadership change and becoming CEO? It’s a big transition. What did you have to get comfortable that you weren’t comfortable doing before?
Look, one of the biggest changes when you go from any in a 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 look at you is 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 do something which 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 on a given day? How do you pivot? You said it comes from resource allocation.
I actually think about it as resource alignment. What I mean by that is, have you heard this term, that culture eats strategy for breakfast? I said this to our team, alignment eats strategy for lunch. And what I mean by that is the biggest job, 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 distributed, as they get much bigger, vectors are totally not aligned.
Can you help me? Where were they misaligned where you aligned them, and what was the outcome?
Think about this, Harry. You have a sales organization that’s optimizing for this quarter. You might have a customer success organization that’s optimizing for the segment of customers staying and not churning. And those two are not always the same. And then you might have a product organization that’s trying to launch a product. And how do you align every one of these functions that are trying to do what they think is right? They’re trying to optimize for subsystems. How do you get them to align on the system?
And the way to think about this is most of the work that gets done in a larger organization is cross functional in nature. They’re not functional in nature. Most organizations grow up with a functional mindset. What am I doing in my team? What am I doing in my function? How do I optimize? And so, really, the alignment is, can we be clearer on what moves the needle for the company? Now, I gave you an example of our strategy earlier, which is we want our product to be easy, fast, and unified.
Now, that’s not just the product’s job. It is the job of marketing to communicate that value proposition to our customers. It’s the value of sales to be able to demo to that and help our customers understand that. It is the job of customer success to make sure that we’re delivering based on that, right? Those are very, very cross functional priorities. Now, if I go to our team and we say, The number one priority for HubSpot today is to make our product easy, fast, and unified, that aligns the entire set of sub functions to optimize for that outcome that we want to drive based on that strategy.
In most organizations, it’s not just about resource allocation. Is it when you allocate the resources, is there duplicate work? Is there clarity in what the resources are going to accomplish in what period of time? Do we know what the goals are? And if something does not work well, is there clarity in who takes accountability to get the right outcomes? And that’s the job. And once you set that up, you begin to see that flywheel work.
When you think about alignment, I think about kind of facing a challenge, bluntly, and you’re aligning against it. And it makes me think of Jay Simons, who I spoke to last night. Oh, nice. He said I had to ask you about wartime versus peacetime CEO ship and hear your thoughts. How do you reflect on wartime versus peacetime CEO ship?
Yeah. Are there different modes, you know, that a CEO needs to operate in? Maybe the modes optimize for different things. You know, when you are maybe in a wartime or a hard time, you are optimizing for speed of execution. And when you are maybe in peacetime, you are optimizing for getting a consensus around what you’re trying to do. And those modes are completely different. And you do have to operate. And the question is, should you be good at one or the other? The answer is you’ve got to be good at both and many other modes of operating.
You know, there are years where you get into the year and you’re like, This is go, go, go. You are optimizing for speed, which means we are going to be very clear in terms of what we want to accomplish this year. We’ve to get like people just follow there. That’s the North Star for this year. We’re just going to go, and it’s optimizing for speed of execution. And that’s completely different when you need to enroll everybody in your strategy. You’re doing roundtables. You’re getting everybody to align on what the priorities are.
And the mode of execution is really different. You’ve to do both. And sometimes, you gotta change the mode in a year or maybe even a given quarter.
You say about the importance of speed then. Can you take me to a time where you move very fast? Yeah. And maybe you should have moved slower. And what did you learn? There’s a moment with people where they know something in their head and it’s like, do I say that story? You
know, I I laugh, Harry, because so I’ve been getting, like, performance reviews forever and ever. Oh my god. Oh my god. Yes. Exactly. And the consistent theme across now twenty five plus years of my performance reviews is go slow. Because I have, you know, natural mode is really going super fast. Very early on, I was in sales, you know, I’d just gotten promoted to a sales manager role. That was the first time I got that feedback. Go slow because your team is not behind you. You need to, like, explain things to them.
You need to ask questions rather than give answers. And I have a sticky that is probably a decade old, and I can’t take that sticky off my computer because it says, Slow down and ask questions. I smiled and laughed because, you know, this is a lesson in the making. My mode of operation is always for speed and speed of execution. And I found that when you spend the time providing the context to your team, when you ask more questions so that they can get to answers, when you enroll them in what you want to accomplish as a whole organization, then you go far.
And sometimes you optimize for speed and you turn around and you’re the only one there. And so, what I’ve learned is that there is a ton of context building when you are making a pivot when you’re changing a direction of something, you have to provide the context, you have to provide the why behind the what you’re asking to do, and that is a process of slowing down in order to go far.
I’m intrigued when you think about making those big decisions and providing context for them. One thing that, again, everyone actually said we should talk about was the transition in in and that’s not fair to say transition, but the moving up also of customer ICP, embracing a larger enterprise client. Yeah. Why did you decide to add mid market and enterprise to the pretty purely SMB HubSpot?
You know, that’s a great question. I’ll tell you then, when I joined HubSpot, this is January 2020, I looked 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 4,500 person company. So well out of our target segment zone and our ICP. It was working beautifully. 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 upmarket? And just so we know, we’re talking about 2,000 to 2,000. 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 2,000 to 2,000. But the opportunity to go to a 1,000 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.
Is it not an entirely different business in the way that you’ve suddenly got to scale an SDR, a BDR, an AE team, a customer success team? These are really complex GTM motions functions. Is it not an entirely different company that you’ve got to build?
No, I don’t think it is that 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’s a myth that there’s a completely different motion and you gotta go and hire all these enterprise class 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 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 1,000 and taking it up to 2,000. That is a much better way of scaling upmarket. And we’ve been able to bring along our reps by upscaling them.
We’ve been able to bring along our partner ecosystem by upskilling them. We’ve been able to continuously drive innovation in the product as we go upmarket. That’s
Where does it feel most different? You know, when you go from 200 to 400 and then 400 to 800 and then eight fifteen, where is that like, oh, this is different to the last phase?
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 maybe the board, then it probably gets a little bit more different. And that’s where we have 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 up market, right?
So, I think there is an organic way of upskilling that you can do to make sure that your team is enrolled in the process, the skills are getting better, and then you begin to set the flywheel in motion.
When we think about the movement up to a higher employee base, you do more and more nudge into Salesforce’s territory. You’ve always Not you, but HubSpot’s always been quite like, Yeah, no, we’re not really competitors. No, no, no. And they’re always like, No, No, no, they’re competitors. You kind of are, right? Look,
it’s a it’s a it’s a very large market. B2B apps are not winner take all markets. It’s different than consumer apps. You know, consumer apps, you see one use case, there’s an app that comes in, and then it’s like 90% of the market is just like one provider. That’s not been the case. Almost any of B2B apps, whether you look at like HR or finance or recruiting or, you you look at like CRM, they all have multiple players. And I think the way we look at it is for the 2,000 to 2,000 segment, 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 enterprise segment that they’re really good at. And so, yes, is there an overlap in the upper end of our upmarket, 2,000 person company? Sure, we see them. And they probably are like, yeah, we have a whole space in enterprise. And okay, there’s some overlap there. So, yeah, are we competitive in one portion of the segment? Yes. But we also focus on really delivering for that entire SMB, which is the 2,000 to 2,000 space we’ve been talking about.
What do you think they do better than you that you’re like, you know, we can learn from that. We respect that and we can learn from that.
I always respect and learn from, you know, competitors. The best competitors make you better. Salesforce does a really good job of marketing and telling the story and creating the narrative. And we look at that and it’s like, you know, we’re very impressed and we learn from it.
What do you think they should learn from you?
Making the products easy. And that’s not what customer platforms applications have been. And so part of what we have been doing is to train the market, train our customers that easy is a really important attribute.
Saying the easy to use product, Pat Grady told me that I had to ask this one, which was when you have an incremental dollar, how do you think about where to invest in? Whether that’s investing in product to make it easier, the product like growth motion more kind of fluid, or actually in a more sales led motion, which obviously increases the higher ACV and touches the larger customer base. How do you think about where to spend that incremental dollar?
If we really had to make a choice, it would be product first. The more you can invest in the product for it to be intuitive, unified, the easier it is to get the sales and marketing engine going.
Oh, I do wanna talk about SMBs in particular with regards to AI because you said something fascinating before. You said AI is history’s greatest equalizer for SMBs. Yeah. 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?
50% of companies that get started fail within the first five years. Starting is hard, but scaling a company is absolutely brutal. 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. They are expertise constrained. They don’t have an army of consultants and resources to kind of like bank upon. So, they operate under constraints, but yet have grand ambitions.
And when I said that AI is an equalizer for SMBs, It removes each one of those constraints. So, 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 customers that you want to be able to prospect and get much better conversion rates. So no need for huge budgets if you’re leveraging AI to send personal messages. And then think about sales. The expertise that you need to sell and you said this earlier you need a presales consultant. You want a demo. You want a solution consultant. You want all these experts to be able to scale selling.
Well, you can get demos done through AI. AI can actually help in a lot of those areas. And so when generative AI came on the scene, we got super excited, not because it was a shiny, cool technology that we all wanted to hype about, but because it unblocks SMBs in the core areas that we focus on, marketing, sales, service. That is exciting. Taking a pretty sophisticated technology, making it super simple.
You mentioned like sales tools. Yes. They can do all these things. Yeah. If you actually speak to most of the customers, they’ve churned and said they’re not very good. And this is for point solutions, which are like purely tailored to a specific part, demoing, interviewing candidates, whatever that is. What is hype and what is reality?
Lot of hype, isn’t it? I mean, look, I think this is why the north star for us has always been customer value. We talked a little earlier about companies slapping an AI SKU and pricing it, and then you begin to see there’s churn. And one of the things that we have focused on is let’s build great product and let’s make sure that there is repeat usage, repeat value with customers. And when we see it, then we can scale it and then we can price it and then we can do all kinds of things with it.
And so, to your point, it’s early, but we are seeing clear signals in terms of agents.
What signals do you think we’re seeing that are most exciting?
Look, I think support is a very clear signal. We have agents, a customer agent that we have. We have 1,500 customers, and within weeks we saw 42 to 45% of tickets being deflected by AI. And that’s 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 driven conversion rates and that has helped us scale marketing. And so, it’s early, but at this point in the technology, we’re looking for signals.
In terms of the slapping on AI, what’s the difference in, like, slapping on AI in the way it should be done for a lot of scale ups? Say your Notions, your Canvas, you’re in that realm, like AI, I think they’ve done it well, the way, but like AI is added to an existing product base. What’s slapping on and what’s doing it the right way?
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. 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? Don’t you think, like, this is the time where you got to dream big and you have to iterate small and you’ve got to start with a couple of use cases and continue to build patterns in terms of customer usage?
Do you worry about margin degradation with the integration of AI into your tools? And what I mean by that is obviously you sit on top of models. Yeah. And you have to pass through a lot of the revenue to them. It’s expensive to use them.
Yep.
That is more expensive than just running traditional HubSpot, though.
First of all, model costs and cost of inference has come down pretty significantly. 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 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. 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.
Who actually is most advantageously placed? Is it startups with no legacy code, much more nimble? Is it scale ups, you know, I don’t know, 500 to 2,000 people? Or is it like your HubSpot’s of the world, your incumbents of the world?
Companies with speed will win. It doesn’t matter whether you’re a startup or a scale up or a grown up like HubSpot, Anybody who operates with speed, can innovate, will win. And at this point, HubSpot is operating like a startup. We have the speed, the agility, the focus, the urgency like a startup. That’s what Do it
always have done?
No. This is a pretty big shift in our culture. As soon as we really pivoted the organization towards building an AI first platform and building all the features for AI, we also said that we needed to become agile. We needed to move with urgency. So it’s What specifically culture
do you do to move with urgency and agility where it wasn’t before? Is it like devolved decision making? Is it removing one on one? I don’t know, whatever it is.
I think it is speed and cross functional decision making that needs to get faster. We talked a lot about alignment. In a company like HubSpot, getting work done is getting cross functional work done. And getting cross functional work done is who’s making the decision, is there clear accountability for the decision, what happens if the project goes south or if it hits a pothole, how are we going to solve for it? And that is the speed that we’re trying to get people to rethink. And I also think it’s about the fluency of what AI can do for us internally as a company as well as for customers.
And so part of driving that urgency is, are you AI fluent? Are you getting better at writing prompts? Are you getting better at use cases within your function? And the more conviction you have in using AI every single day, the more conviction you’ll have in educating customers and getting customers on AI.
I got told I had to ask this one. How do you personally use AI every day? You said about writing prompts there.
I do. Look, I think my workflow has changed quite a bit. I have Claude with few projects set up.
You have Claude?
Yeah. I have like projects within Claude set up.
Wow.
And there is one Why do you
have Claude?
I mean, I have all of them. So I have Gemini Gems. I have I’m
just intrigued why Claude. So I’m gonna I lose friends because, like, Mike Crieger was just on the show. And and, you know, and I put
in
a prompt Okay. For Yamini.
Okay. And did
it. Yeah. I I did for every single show. And I do it across Grock. I do it across Perplexity, OpenAI, Deep Research, and Claude. It comes out with amazing ones from Claude. And it says, Yamini said this, and Yamini said this, ask her this. And I say, amazing, where did Yamini say that? And it comes back, oh, we didn’t know you actually needed real statements, she said. And I’m like, woah, woah, woah. I could have said to her, you said this, And you’re like, no, didn’t.
These are very, very bad. Then
you’re talking about sourcing and citation, which is really important in certain use cases. I’ll tell you, I use it to write my LinkedIn posts, I use it Do you find
it
help
better than OpenAI?
In certain cases, yes. And I will tell you that I have a project for earning script writing and I’ve literally fed it with the last 16 quarters of earnings script. What
you do? You feed it, like the PDF? Yeah,
it’s basically all of the docs of the last 16 earnings script. I fed it into Project. And when I’m about to write the next one, I give it, you know, here’s the parameter of the story that I want to say. Use the approach that I’ve taken in the past 16 and help me write and think through it. It will think through it. And then I’ll ask prompts of, if I needed to make sure that I communicate this message, can you improve it? And so reasoning, thinking, sorting, analyzing, and then writing is super useful.
And it’s actually really shortens the time. I write every one of the earning scripts. And I now use combination of Claude and a couple other models. I do the same thing, is I’ll try a couple of different outputs with the same prompts and see which one I like better. And that has helped me refine my thinking.
Can I ask, what is your process for writing an earnings script? Do you sit down and do it in one session? Do you do it over multiple How does that look?
Earning script or any writing in general? You’re in an earnings script? Yeah. It’s one session.
Wow.
It is one session. That’s long on me. Sunday afternoon, probably three hours to four hours, and it’s much more about what is the Now clear narrative you wanna have a thought partner and a reasoning partner and a creative partner for doing it. I used to do it all by myself. I’m like, Ugh, get me through the Sunday afternoon. Now, I’m actually enjoying it because I’m like, Did I get this message across in this paragraph? Analyzes it. No, you could probably say it this other way. And so, I think it really helps with being a partner in terms of some of this process.
And it’s, you know, I actually enjoy it. You know, as much as I say it’s a lot of work, I really enjoy it because it is a time for me to reflect on the past quarter or reflect on the year and think through where did we make progress, what has worked, and how can we clearly articulate that story to a really wide audience.
This may be way too in the weeds. Sure, go for When we think about SEO today, I’m sure a lot of HubSpot’s traffic is SEO.
Yes. It is.
An unbelievable content engine. SEO is slowly transitioning from Google and from search engines to ChatGPT and to other providers. How do you think about that? Is that a concern?
Well, it has been something that has been happening for a few years, right? If you look at the SEO traffic, especially after AI overviews and what perplexity and some of these sources actually provide. The big shift that does happen, Harry, is search engines used to provide blue links that you can click and then reach someone’s website. Now they’re providing answers, which means you no longer need to click. And I think that’s a shift that’s going to continue for a while.
Then you were sponsored beneath that, and then suddenly you’re page two, page three.
Exactly. So I think there is a whole process that’s going to happen. I don’t think that this is surprising to us. We’ve been really looking at diversifying our content strategy for the last three to four years, even before AI came in. That’s a process of expanding to podcasts. We actually brought a podcast network and as you know, we get like millions of users listening to our podcast. We’ve actually bought a couple of email newsletters, old style email newsletters, and those get like daily coverage and provide us another way to expand kind of our distribution.
How do you
think the ROI of those media acquisitions? You know, I know them and they’re fantastic properties and well done for them. But how do you think about the ROI of conversion attribution versus brand and marketing? It’s difficult to do.
It’s just distribution. It’s like top of funnel. I don’t think that there is one user who’s just gonna listen to podcasts and immediately buy a product. But the awareness building, how do you think about brand in overall? The level of awareness of your brand and the level of multiple touches it takes for someone to look at your brand and then continue the process of being even more curious about the brand and then getting converted into sales, that’s a multi touch attribution model. I don’t think like we look at it on single property basis.
It’s the how is our overall awareness increasing across these multiple channels.
It’s very difficult when you think about the shift away from SEO. That is one that I’m just spending more and more time thinking about.
The way we think about it is where are our customers? It used to be the customers just visited our website. But today, they are on YouTube, they’re on Instagram, they’re on other, you know, TikTok, and they’re on LinkedIn. And you need to be where your customers are, not just expect them to come to where you are, which is your digital presence, which is what SEO helped us do, which means it’s a much more customer centric marketing strategy, which I love.
One of my favorite segments is the quick fire segment, though. I’m gonna say short statement and you’re gonna give me your immediate thoughts. Does that sound okay?
That sounds good, let’s
So what do you believe that most around you disbelieve?
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 gonna monetize it? And what’s 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 pricing is to maximize every dollar and therefore get to revenue maximization.
We actually think about it as market share maximization, which means you’ll approach pricing very differently.
You can buy and hold one public stock for the next ten years, not HubSpot.
No, Microsoft. I think Satya Nadella is like one of my all time favorites. He’s just done such a phenomenal job.
What do you learn from Satya?
How he has bet all in, first on cloud and now on AI. How he has used culture to pivot the company. How he has instilled this growth mindset and curiosity within a company that seemed super siloed, you know, before he started. I’ve read the book Hit Refresh and was obsessed with it. I’m like, This is amazing. This is just a whole lesson in terms of company building. And he’s just done a phenomenal job. And he talks to customers, talks to partners, talks to investors, new companies.
I’m like, That is incredible.
What board member do you not have that you’d most like to have?
The CEO of Anthropic. I think he is just phenomenal. Deep research, exceptionally well thought out process for safe AI. Just a researcher of incredible caliber.
I’m gonna get in trouble, definitely, then for my review of Anthropic. What few, I’m like, Oh, no, I shouldn’t have said that now. What have you changed your mind on in the last twelve months?
Okay. I have a personal story. So my son is applying to universities.
I
wanted him to be in California. That’s where we live. I’m like, you gotta stay here. There are like plenty of great schools. He’s just like really focused on East Coast. And we went there. We looked at the colleges. He fell in love, you know, with East Coast. And I changed my mind. I saw him there. He felt really at ease in a completely different part of the country and very supportive. He’s going to university in the East Coast.
Does being a parent make you a better leader?
Definitely more patient leader. I have two teens. And a lot of times what I go through with my teens is exactly what I’m going through at HubSpot. We also happen to be in teenage.
There’s a brilliant book, Speak So Children Will Listen and Listen So Children Will Speak.
And it
actually talks about kind of how to communicate to children and teens effectively. And it being very much largely the same.
I’ll have to buy that.
I’m gonna go there, why not? Unlimited vacation, mental health days, no meeting Fridays. Was this just like signs of woke times or is this like a part of culture?
Hey, we just actually made a change from unlimited vacation times to flexible time off. That is something that we have moved the culture around. Now, a lot of what you talked about happened in 2020, 2021. And those were times that, as a humanity, we were going through pandemic for the first time, and people were losing their lives, livelihoods. 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. We’ve now really refocused the company in terms of customer outcomes, mission orientation.
We just made this change into flexible time off. Don’t ask me how it goes.
I’m actually not. I’m gonna leave it there. Really like you. Thank you. Concerns you most in the world today?
I read a stat recently that gender parity at the rate that we are improving it is going to take one hundred and thirty four more years. It’s going to take one hundred and thirty four more years to get to gender parity just across broad health, longevity, the kinds of work that we do, the pay, all of that, that’s a really long time.
Do you not think we’re seeing a reversion in the work that was done over the last years? It’s one of those actually sad truths, but when you look at good times, see things like gender parity being more of a focus. Bluntly, when times are hard, shit, inequality is worsening, conflict’s happening. Respectfully, it is not a priority and it is instantly deprioritized.
I know. I know. And that’s scary. That’s scary.
Very scary. It’s like climate Yeah. Very similar. Yeah. What’s the biggest surprise, or what thing do people not understand about being a public company CEO?
It’s a rollercoaster ride. Every year, there’s some new challenge, and you don’t know what the challenge is going to be, and it’s a rollercoaster ride.
Do you find it hard to regulate yourself when it is very volatile?
I think you have to have good practices for yourself to ground. And for me, it’s been meditation for a very long time. Meditation and yoga. So there are things that ground me, and that is important to me and centers me. And so, yeah, there’s a lot of volatility. There’s a lot of uncertainty in the role. Every year feels very, very different than the previous one, but you gotta ground yourself.
One thing I find hard is that when companies reach a certain size, no matter how good everything is, there’s always one thing that’s bad. Yep. In every company at a certain size. There’s something that’s wrong with HubSpot today.
Oh, of course. And
so you can always choose to be down.
Do know what I mean? Absolutely.
It’s hard.
Absolutely.
And if you’re a perfectionist, you focus on that thing that’s wrong. I know 98 is good, but that sales motion is not working.
That is right. I’m struggling with that.
What question are you never asked that you’re like, I wish people would ask that?
You know, Harry, the number of times I get asked the question, are you going upmarket? So there’s That’s like a a
shit question. Who no would ask that? Right? Right? Then And it then comes it 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 become a very large company is by going upmarket. And I wished 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, ten 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.
That’s a terrible question about moving up market. I can’t believe people ask that. You’re right. Yamini, I’ve so enjoyed doing this. Had, Ally said so many good things from everyone. This has been such a pleasure to make happen.
Thank you so much for having me here, and it’s such a fantastic experience to do it live with you here.
It is so much better. Yeah. This has been amazing. Thank you.
A lot. Take care.
That was such a special show to do in person. I wanna thank Yamini for coming to the studio in London. If you wanna watch that, then you can find it on YouTube by searching for 20 VC. That’s two zero VC on YouTube. But before we leave you today,
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