EP 132: Yamini Rangan (CEO, Hubspot) On Sales and Marketing Frameworks That Win in the Age of AI

Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she’s mastered. She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-first businesses and what it takes to stay competitive in an evolving landscape. (00:00) Intro (00:56) Yamini Rangan's Background and Career Journey (02:33) Joining HubSpot and Early Challenges (03:49) Transition to CEO and Leadership Insights (07:33) Strategic Planning and Long-Term Vision (15:15) AI Transformation and Product Innovation (18:57) AI's Impact on CRM and Future Prospects (28:51) Content Strategy and Customer Engagement (37:34) Contextual AI Features for Better Usage (38:13) Human Expectations and AI (39:36) AI in Daily Productivity (42:54) The Art and Science of Sales (51:05) The Role of Curiosity and Resilience in Sales (53:23) Evolving Company Culture (55:27) Leadership Style and Management Lessons (58:27) Scaling Startups: Lessons from Workday (01:02:54) The Future of AI and Incumbents (01:14:10) Concluding Thoughts Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Logan Bartlett?

  Welcome to the Logan Bartlett Show. On this episode, what you're going to hear is a conversation I had with CEO of HubSpot, Yamini Rangan. Now, HubSpot is a $40 billion business in the CRM space. And Yamini, I talk about a number of different things, including how AI is transforming go-to-market, the key lesson she's learned as a first-time CEO, the sales tactics she's mastered and going from an engineer herself to leading sales organizations, and the strategies that she has employed when businesses are going through major pivots, including how to transform into an AI-first business. You'll hear that conversation with Yamini here now. Thanks for doing this.

• 0:45Speaker 01

  So happy to be here.

• 0:46Logan Bartlett?

  A pleasure to have you. I think HubSpot might be my first two time from a single company. We did Brian maybe two years ago.

• 0:55Speaker 01

  That's right.

• 0:56Logan Bartlett?

  And now.

• 0:57Speaker 01

  Thanks for having me.

• 0:58Logan Bartlett?

  Yeah, I'm a big fan of HubSpot. So maybe for people that are listening that don't know, can you give a quick synopsis of your background to joining HubSpot and then your role now?

• 1:09Speaker 01

  Okay, super quick synopsis. I spent the last like 30 years in the tech industry, first as an engineer. I started as an engineer, you know, built some code, then went to business school and came out of business school in 2003, which was another kind of very recessionary time, and joined Siebel, the original CRM company, in their sales organization. Spent a decade in Siebel SAP, mostly in sales, value-based selling, and then spent another decade across Workday and Dropbox, both before going public, all the way through public, and a little bit of scaling. So I would say,

• 1:52Speaker 01

  learned a ton of scaling in those two companies and then joined HubSpot in January 2020. Who knew it was going to be such critical times?

• 2:02Logan Bartlett?

  I joined Redpoint in March of 2020.

• 2:04Speaker 01

  Is that like, oh, okay, your timing is even more.

• 2:07Logan Bartlett?

  March 2nd. I think I got seven days on the ground.

• 2:10Speaker 01

  Seven days on the ground. I had, I felt better now because I'm, I got like two months and seven days.

• 2:16Logan Bartlett?

  It's, it's, it's, I, I, I kindred spirit on this one. It's a weird, uh.

• 2:20Speaker 01

  It was a weird time.

• 2:21Logan Bartlett?

  It was weird to get to know people and all of that stuff. I, I sort of had some arrested development of like getting to know my colleagues and it just, it was, uh, it was an unusual time to start a job.

• 2:31Speaker 01

  It was, and it's so funny. You, you talked about, uh, to Brian, right? So I joined in January and he's, he says, take your time, go slow, meet people, get out to different offices. And then March happens and he's like, go fast. You can't travel. Get moving. What are you doing in five days?

• 2:50Logan Bartlett?

  I mean, it was crazy. And people forget now, cause I think COVID's thought of as the acceleration that it became in the Zerp era and all of that stuff. But the first like month or something was total panic. I remember thinking like, hey, I switched jobs and now I, I probably won't have a job in six weeks' time. Like I know I'm at this new firm and they're just gonna fire me. It was a lot of mental oscillation on that. And then, so, so you joined as, what was your title when you originally?

• 3:13Speaker 01

  Chief Customer Officer. And you know, um, we have this concept of flywheel. How do you bring marketing, sales and customer success together and put the customer at the center? And when you do, you attract customers better, you engage with customers better and you delight customers. And we call that the flywheel. So, uh, the whole idea was that I would come in and take care of this flywheel organization and, um, drive our next phase of growth.

• 3:41Logan Bartlett?

  So, so you had, you joined the, there was a weird, uh, beginning and then COVID happened and it was kind of off to the races after that six week period of time. And then, uh, uh, March of the following year, so 14 months later, you ended up taking over as interim CEO?

• 3:57Speaker 01

  That's right. That's right. So, um, the first year was crazy. At the end of first year, I still remember, uh, it was Christmas Eve. And Brian texts me this article of Jamie Diamond.

• 4:12Speaker 01

  And the article was about Jamie Dimon had to have a critical surgery and he hadn't figured out his succession and he talked about how important it was to have made those decisions. And so he he forwards me this article and he says, if I get hit by a bus, then you're my successor. I was like, you're not gonna get hit by a bus, so let's not worry about that. And that was it. And then March happened and unfortunately, he did have an accident. So he literally says, remember that conversation? Take it on and run it.

• 4:43Logan Bartlett?

  It wasn't a bus, it was a snowmobile, but it was a, which Brian and I talked about, we'll link to that episode if people want to hear that story. But ultimately, he's doing very well today. But he, how long was he?

• 4:57Speaker 01

  He was out, well, we didn't know at the time of his accident, but we knew it was going to take a few months. And our first thing was, you need all the space and time? We've got this. And so I do think that the whole leadership team stepped up. It was, it was, you know, everybody recognizing he needed the time and the space. And then he came back and he's doing really well. But he came back in August of 2021.

• 5:23Logan Bartlett?

  And he came back and said, you you had all these things ready for him? Hey, Brian, I want to run these through with you.

• 5:29Speaker 01

  I had a long list for him. And I was like, here are all the things that you should be doing.

• 5:33Logan Bartlett?

  Win CEO back. Here's what I need. And what did he say to you?

• 5:37Speaker 01

  He was like, great, do it yourself.

• 5:39Logan Bartlett?

  Yes. So you became the full time CEO then at that, at that point in time. I guess I'm curious, I mean, not not a position many people have gone through in the public markets, right? All of this is happening and you guys are, you you have responsibilities to your shareholders, you have responsibilities to your employees, to your customers and all that. I'm curious when that moment happens and you realize you're going from this interim title to the to the full time title. Like, what is that mental shift? Or how long did it take to really set in that like, oh, gosh, I need to drive this bus now?

• 6:10Speaker 01

  It hasn't quite, you know, set in that quickly. Now, I was doing it on an interim basis and I was very clear that Brian had, you know, a long list of things that he should be doing. And you do it, you know, when you are an interim CEO and you're, you know, you're kind of caretaking. You're like, I'm not going to make any architectural changes. You know, I just want to make sure that everything is right. But then when you are taking this on, you got to look at the foundation up. And that is, uh, that takes a brief moment. And the number of stakeholders you now have to consistently manage just broadens immediately.

• 6:49Speaker 01

  When I came in as a chief customer officer, it was the customer partner and certainly all the employees within my team. And now you had the board, you have investors, you have, you know, stakeholders that are kind of much broader in nature. And that takes a little bit of time getting used to. And I think the fact that Brian, uh, is a visionary, you know, leader. And he'd done such a great job. He'd led the company for 15 years and you sit there wondering, really? Like, I'm gonna follow this. You, as a CEO, you mostly want turnaround situations. You know, this was clearly not a turnaround situation.

• 7:25Logan Bartlett?

  You want the bar set low, so you can easily exceed it.

• 7:27Speaker 01

  You want the bar low, but this was like, okay, this is a high bar. So how, how are you gonna do it? And I think the way I looked at it is I can get overwhelmed with all of those things. Or I can look at where should HubSpot be in five years? And what would I feel very proud of having accomplished for HubSpot in the next five years? So let's just go and build that. And that's kind of the working backwards is how I, I looked at it. And honestly, that, that saved me a lot of like sleepless nights.

• 7:55Logan Bartlett?

  So, so five years in the future, cause it's an unusual situation. Cause Brian's still involved, he's executive chairman, right? Co-founder Darmesh is still full time, right? And so, so you have, you're taking the stewardship for the thing that they created while they're still around in some ways. And so I guess it was five years, the right time to pick in the future. And you're like, all right, this is where we're going and you get their buy-in on it? Or how do you sort of orient around those balances?

• 8:24Speaker 01

  It, it is a lot of balancing and I would say that I've now, um, I I think one year is too short and I actually feel five years is too long. And uh three is about right. Because you you can accomplish a lot more in three years than you think. And you you know, one year seems always overwhelming to accomplish. So I've kind of, you know, I think if I were to redo it, I'd probably say three. But now I'm like always it's the next three year plan. So we actually have a cadence built into HubSpot where every Q two, we call it the think big season. And it's the strategy season. And the only thing that we think about is what are we going to be in three years from now? And how do we build towards it? So I think three years is a good season to do it.

• 9:09Logan Bartlett?

  When when did you start doing the three year plan?

• 9:11Speaker 01

  I mean, we've always had the strategy planning process. But uh certainly in the five years I have been, it's always what's the next three year plan look like?

• 9:22Logan Bartlett?

  That's interesting.

• 9:23Speaker 01

  Yeah.

• 9:23Logan Bartlett?

  Do you do you find you have pretty good accuracy around it? Or is it more the exercise? Yeah, the exercise is probably good.

• 9:29Speaker 01

  The accuracy is so poor.

• 9:31Logan Bartlett?

  Yeah.

• 9:31Speaker 01

  I mean, the first year we did it, we didn't know that you're going to go through huge digital acceleration. And twenty twenty one, we were talking about that. That was uh eighty one percent net new error growth. One of our fastest growing years. We were billion and we added like five hundred, you know, million to it like almost immediately, right? So no, we didn't plan for that. And then the following two years was a lot of digital optimization. People pre bought a lot in one year. They bought a lot of stuff and then they were consuming it over the next two years. And so obviously those two years were were not right. And then, you know, there's gen generative AI. We'll talk about it.

• 10:11Logan Bartlett?

  I want to talk about, yeah, I'm very interested in that.

• 10:13Speaker 01

  So it's none of those are are very accurate. But the fact is, you have to think about where is your customer going to be three years from now? And what's the best thing you can do to serve those customers? You know, even before they can articulate their needs. And that allows you to think much more broadly.

• 10:32Logan Bartlett?

  Hmm. And so so is the exercise itself then the reason you keep doing it despite the um the mixed uh accuracy? Uh is it just is it just helpful to get the team outside of the day to day and the the normal cadence of it? Or is it? Future-proofing and making sure you don't get disrupted from something orthogonally and that you're really thinking in the future of where things can come from?

• 10:55Speaker 01

  It is a combination of both. We run such a monthly business. It's a tight business. You're constantly thinking about what's happening this week, this month, this quarter.

• 11:05Logan Bartlett?

  Sales cycles are quick.

• 11:06Speaker 01

  And sales cycles are super quick. So we ask ourselves two questions. What are the decisions that we need to make in order to compete better and deliver more value for our customers in the next three years? And what are the decisions if we don't make today will disrupt us in the next three years? And those two questions, when you ask it consistently, we actually take, you know, a couple of months to write prompts. And the prompt writing process actually makes us all think about both of those questions. What should we be doing and what are we not making decisions that's going to disrupt us? And we go through the process of thinking, debating, discussing, and bringing together

• 11:49Speaker 01

  kind of all top, you know, leaders within the company. Healthy exercise, super healthy exercise.

• 11:56Logan Bartlett?

  I feel that HubSpot was at least, I worked in Boston for three years in venture.

• 12:03Speaker 01

  Oh, great.

• 12:03Logan Bartlett?

  Yeah, and it was pre-HubSpot IPO, but I knew the team and the ecosystem. And I feel like it was maybe certainly never expected to be the success that it has been today. I think it was always a

• 12:18Speaker 01

  Really?

• 12:18Logan Bartlett?

  A strong business.

• 12:19Speaker 01

  I think Brian and Dharmesh would disagree.

• 12:21Logan Bartlett?

  I think they would disagree, but I think they would say that they were underestimated along the way. I think they would agree with that. I don't think the initial investors were expecting it to be a $40 billion plus company. I guess as someone, now you're the steward of it and guiding the ship in a meaningful way. But I guess in coming in, both in the interview process of taking the job and then once you got there. What do you think as a student of business and software and all that? What do you think HubSpot got uniquely right? That's allowed the company to scale to the level it has today.

• 12:54Speaker 01

  Yeah, look, when I was talking to Brian and Dharmesh, this was in 2019. I was looking for what were the founding principles? And what were the founding insights for the company? And what is maybe not as well understood is that Brian and Dharmesh made some counterintuitive bets. And we've continued to make counterintuitive bets. Insights that are uniquely well positioned for you to drive results based on. So the first one was SMB is a big market. Every single time, even now, I get asked the question, are you going up market? Are you going enterprise? And there's just this common belief that you have to go up market in order to scale.

• 13:34Speaker 01

  And the first belief that we had is that the 2 to 2,000 space is mid-market. It's a huge market and point solutions or enterprise solutions don't serve them well. And we have a unique value proposition. That was number one. The second is that you have to be, you know, you have to be something special to become a platform. We believe that we needed to be a platform and we needed to be an organically built platform. You know, I talked about Siebel. You go into SFA and then you acquire a bunch of things. That's the playbook for CRM companies is you start with one product and you buy your way into other products. That just creates a clunky experience for your customers.

• 14:16Speaker 01

  And so we had this counterintuitive belief that if you built it organically, one, you can actually speed up your organic pace of innovation, because any primitive in the platform layer would benefit every one of your hubs. And two, it actually benefited the customers better. And that was probably even more important. So I think the counterintuitive beliefs, and I think the couple of the ones that I really appreciated, you know, is around culture and how you think about culture as another product. And you constantly evolve. You know, imagine a product that you saw 10 years ago. Uh, the UX has changed, probably the underlying data structures, the application logic, everything has pretty much changed. And it's the same thing with culture.

• 14:59Speaker 01

  You have to have some core tenets around culture, but you're constantly evolving it like a product. And so, uh, to me, those three were unique and, um, some things that I believed in. And that's why I've kind of continued to double down on those beliefs and those core strategic choices that they made.

• 15:18Logan Bartlett?

  Hmm. And so, so, uh, ChatGPT happens in, I guess it was fall of twenty two.

• 15:24Speaker 01

  November twenty two.

• 15:26Logan Bartlett?

  Twenty two. And, uh, and you had been, you had been on board for, uh, two and a half plus years, almost, almost three years.

• 15:34Speaker 01

  Yeah.

• 15:35Logan Bartlett?

  And in the CEO seat for however you want to score it, interim versus full time. I guess when, when that happens and you start, uh, realizing that this is going to have big implications, what, what do you do? How do you, how do you become AI native in some ways?

• 15:50Speaker 01

  Look, it is, uh, remember that beautiful strategy planning process that I talked about?

• 15:55Logan Bartlett?

  Yes.

• 15:55Speaker 01

  That process carries through. You have a plan, an annual plan and a product plan and go to market plan. We literally came into the new year and we threw out all of that.

• 16:05Logan Bartlett?

  So, so November it happens, by January you're like, we're done.

• 16:07Speaker 01

  Done. And, uh, we said, this is, this is too big and we're done. And I remember having a conversation with Brian Dharmesh and our top product leaders. And we're like, we're changing our entire product roadmap and we need the first features delivered as quickly as possible. And we started like experimenting and we pivoted the company, pivoted the roadmap. And we said, we need to go fast on this. Our first product, uh, features were released in March twenty twenty three. It was the first version of ChatSpot because the thing that we saw is, uh, you now have a natural language interface into everything that you do within the application. So ChatSpot was our generation one of the product

• 16:52Speaker 01

  where you ask a question, you can get answers from HubSpot as a CRM. And then the other thing that we, uh, launched was content assistant, which is again, Very early on, you knew that content creation, content generation and content, you know, diversification, personalization was going to get completely changed. You know, remember 2017, 2018, we were all asking the question, what's the next big thing? What's the next big thing? And the next big thing is staring at us. And you know, with AI, you can ask questions and get very different answers than ever before. You can look at the potential of the technology and you could say, all of the things that you were never able to do in sales, you now can do in sales.

• 17:37Speaker 01

  The time it took for you to research companies, the time it took for you to discover, all of that changes. So, you know, you look at this technology and the reason all of us got excited was that we could solve age-old problems that we've never been able to solve within the CRM industry with this technology. So, it wasn't, you know, I describe it as a pivotal moment, our roadmap changed. But then, we didn't quite see the full potential. I think that's why, I think it happens in stages. The first stage of it is table stakes, rule basics, right? We can summarize contacts, we can summarize content, we can create content, we knew that was possible. But we also know that there's a couple more stages to play out.

• 18:19Speaker 01

  Uh, the stage that we are in with AI is differentiation. How do you create unique value for your customers that nobody else can actually do? And I think the stage after this is reimagination. You know, uh, we always think about this and say, we're not building a faster horse, we are building a new car. How does that new car look like with AI in CRM? And that's the reimagination process. So I do think that the industry is going to go through all three phases. We are probably right in the, in the differentiation stage right now.

• 18:54Logan Bartlett?

  So, it, it's interesting, I was gonna ask you this. So, so there's the table stakes stage.

• 18:58Speaker 01

  Yes.

• 18:59Logan Bartlett?

  Then there's the differentiation, the reimagination. And so, uh, now we're in this world of people differentiating with some of the existing solutions. As you think about the reimagination stage.

• 19:08Speaker 01

  Yeah.

• 19:09Logan Bartlett?

  Is there something for someone that's listening that understands what CRM is? Or maybe is thinking about how this is going to impact their life in the B2B context?

• 19:17Speaker 01

  Yeah.

• 19:17Logan Bartlett?

  Is there a use case or something that you think about? Like, this is clearly going to happen.

• 19:22Speaker 01

  Yeah.

• 19:22Logan Bartlett?

  And we might not be there right now.

• 19:23Speaker 01

  Yeah.

• 19:23Logan Bartlett?

  But it's going to reimagine how we work.

• 19:24Speaker 01

  I actually want to talk about the differentiation and then I'll kind of, you know, extend that to re-imagination. So when we say, what gives us the ability to differentiate right now? It has to start with data. And, you know, we all know, like, structured data is what is in a CRM or has been in a CRM. You buy a CRM because you want a company record, a contact record, a customer record, and you want to have all the conversations of when you close the deal and how the deal progressed. All of that is the core thing within a CRM. And we've always been really good at that. What has changed, Logan, is what you can do with unstructured data.

• 20:07Speaker 01

  Eighty percent of the conversations that you have with customers is unstructured. It's not in your structured fields within the CRM. It's in the emails. It's in Slack conversations. It's in Zoom meetings. It's in phone calls. It's in all the transcripts. And there are new things that you can now ask of unstructured data in real time to get better insights. And we're so excited about that because we are uniquely positioned. We have, you know, 1.8 million CRM weekly active users. And every day, they're generating all of these conversations and they're using this. So I think we get excited about what we can do with bringing structured and unstructured data together.

• 20:52Speaker 01

  But then it's more than that. The second part of the differentiation is what's the context that you can bring across these two? So imagine... You hiring a new person at your company, you onboard them. And the way you onboard them is to say, this is the voice of the company. This is the tone, this is the language that we want to use. This is our ideal customer. This is our value proposition. That's and a whole bunch more, you onboard. How do you now onboard agents without that context? So there is a context layer on top of that data layer, which is, you know, something that we believe we can uniquely provide because we look across the whole customer journey

• 21:33Speaker 01

  and we can connect the dots and we can give the agent all of the context. Otherwise, you're going to lead to having point agents, very much like point solutions and point apps. They didn't work. So point agents are not going to work either. So we think that there is a ton of differentiation in our strategy and how we're going to be able to bring that. And I think we also believe that the future is a hybrid, you know, workforce, where it's agents and humans working together and augmenting each other to get better results. And in that, you know, world, a network of agents is really important. And that's why, you know, we have agent.ai,

• 22:17Speaker 01

  which Dharmesh is so passionate about. You can see him like post on LinkedIn mostly at 3 a.m. in the morning. And he's excited because the future looks like agents talking to agents and helping humans to do better things. And we're creating a very vibrant ecosystem where people can build and users can leverage it. And we want to make it all easy and simple for our customers. So there's a lot to be done in that differentiation phase, and we're super excited about it. Now, the reimagination phase, which is definitely coming up next, is what happens with all of this? I think, you know, it's, we'll have to extend our imagination.

• 23:02Speaker 01

  You know, go back to App Store. When the App Store was first created and apps started coming on mobile, you had like the basic apps. You basically converted everything that was on your desktop into mobile and put it into an app and you said, oh, that was innovation. And then four or five years later, DoorDash came about, Airbnb came about, Uber came about, things that you never thought were possible in the pre-mobile, pre-app era just happened and that required a little bit of a settling phase. I think that's what, you know, needs to happen. But, you know, you can imagine CRM to be hands-free and that is profound. For the twenty-plus

• 23:44Speaker 01

  years that I have been in go-to-market, you know the single thing that I've struggled with? Getting sales reps to input basic stuff into CRM. Nobody wants to do it. It's such a waste of time. Let me write to you about the customer meeting I had. Let me write to you about the conversation we had there. Nobody wants to do it. But if CRM can now listen to your emails, listen to your conversations, listen to all of the transcripts that you have, then why do you have to type something into your CRM in order to communicate to the rest of the team? So I think there's a future where it's hands-free. There's a future where CRM is actually listening to the conversations that are happening. And

• 24:28Speaker 01

  there is a future where we have compulsable UI. And that in and of itself is also profound. If you think about SaaS, it is point, click, configure. So configuration and ease of configuration was a pretty big deal in SaaS apps. I think when we think about the next five years in CRM, at least in applications, it is, you know, compulsable UI. You ask a question, "How's my pipeline doing?" And your CRM should say, "Your pipeline is doing better than last week. Here are the four regional views of your pipeline. Go take a look at Europe

• 25:13Speaker 01

  because somehow they're lagging behind in pipeline creation." And specifically, look at these four teams that don't seem to be, you know, getting their job done. That's what your CRM should do. And so I do think that there are constructs of how this can really develop. But I think we need to keep expanding our imagination to be able to get there.

• 25:33Logan Bartlett?

  It's, it's an interesting point. We're talking about the data centricity and the opportunity you have to do a bunch of things when you have that atomic unit, which is the customer record.

• 25:44Logan Bartlett?

  Whatever the case may be, one of your big competitors went on a podcast not too long ago and made the case that as we move to more of this headless CRM, composable CRM, it might make products like CRM, crud databases, I think was his word on it. And I think the implication being it would be easier to swap systems than it was otherwise. I guess, how do you think about the tension that exists between maybe UI lists being, people aren't logging in every day to the same extent versus on the other end of the spectrum is, well, yes, but you have the data and the data architecture and all that, which gives you an opportunity to do a bunch of different things. I'm curious your perspective.

• 26:27Speaker 01

  Well, look, first of all, I have a ton of respect for, you know, every one of those leaders. They have led the industry. They have some incredible perspectives and I've, you know, looked at, listened to, listened to your podcast. I think, you know, it's, it's great. It's, I wish it were as simple as, you know, you have a crud database and you're just like, you know, all of that disappears, the SaaS layer collapses and, you know, things begin to work magically. That is really not the world that we are in. I don't see us going into that world anytime soon. And so the constructs of what you do need to get out of, you know, this massive transformation is, can you provide customers an easy ability

• 27:11Speaker 01

  to access all of their data? Can you make that interface more intuitive so that they're not asking questions, they're not coming in every day and, you know, clicking and pointing and configuring? Can you be much more intuitive and can you provide answers to help them grow? Like, our mission consistently has been helping small and medium businesses grow. Can you imagine a 50% or a 500% company becoming prompt builders, LLM experts, knowing the difference between DeepSeek R1 and O3 and which one they should be doing? Absolutely not. What are they waking up thinking? They wake up thinking about growth and they wake

• 27:54Speaker 01

  up thinking about how in this resource constrained world can I grow? And if there is a technology, it needs to be easy, it needs to be simple, it needs to have fast timed value and it needs to be unified. All of that actually requires work. So I don't see a world where everything collapses and it it just becomes, you know, super easy. There's a lot of work that we need to do to get a powerful technology like AI and democratize it for the segment of customers that we serve. And that's why it's super exciting.

• 28:27Logan Bartlett?

  Hmm. On the content side of things, it's obviously, we we live in this world of proliferation and personalization of content. And I think I I heard you say AI-driven personalization has led to, I think, eighty-two percent increase in conversion rates at HubSpot. How do you think about content and conversion rates and what role AI will play for HubSpot customers or any business that's sort of thinking about these things?

• 28:55Speaker 01

  Logan, when just AI came on the scene, everybody's like, we have to create more content. You can create more content. But when you create a lot more content, you know what it's called? Spam. It is spam. Like, we talked about email spam ways ago. And, you know, if you use AI just to generate a bunch of, you know, content and throw it out there, that is spam. So we've been really focused both internally within our marketing team, but also with our customers to really drive a level of personalization and insights. And so you mentioned the eighty-two percent, which is what we shared at Inbound last September. What we did is this. When people come to the website and, you know, they look around our website and they give us the email,

• 29:39Speaker 01

  we didn't just send an email follow-up back. We used RAG to reverse look up which company they were coming from, what their role was, what conversations they've had, the intent that they have. And we have all of this access, right? This data. And then we looked at all of that and we said, let's use the data to then look at our academy courses and the content that we already have and personalize a response back to them. So we did that. And literally, those email responses, the personalization drove eighty-two percent conversion. So it is not about more content. It is about better, more personalized, more authentic, more insightful

• 30:24Speaker 01

  content. And if we can get the construct to go from AI helps us generate a lot more content to AI helps us Get insightful and personalized content, then you can win with AI. And that's what we're doing internally. That's what we're doing with our content hub and marketing hub and helping our customers really understand how to win with content in this new world.

• 30:49Logan Bartlett?

  Are there roles that you think about within an enterprise or an organization that you think will be far more important in the future than they are today as we sort of move on this AI-driven journey?

• 31:02Speaker 01

  I think every employee that becomes AI fluent will become more important than anybody who is not AI fluent. And I think every role is going to go through a phase of evolution, right? Think about support. And this is the primary use case. Everybody knows that it's, you know, AI's number one probe and high-value use case is, you know, within support. Very soon after we pivoted our roadmap, we said to our support organization, can you go and leverage AI to support our customers? And they did.

• 31:44Speaker 01

  As of last year, thirty-five percent of our support tickets are being handled by AI. And I think we'll push the boundaries for this year. But if you take your question and apply it to support, a lot of our support agents are now doing more premium kind of support. They are doing more complex support. They're actually becoming more proactive. When they see a customer who is getting on-boarded into our product, gets stuck in certain places, they're like, hey, can we help you with this? Or here are things that you can do. So their jobs are evolving from support to being much more proactive, you know, in providing technical assistance. And so you can imagine almost every role becoming that way. So.

• 32:26Speaker 01

  Anyone who is AI fluent is going to win in the next, you know, five to 10 years.

• 32:33Logan Bartlett?

  HubSpot was built very SEO oriented, I think, and did a great job of content and would pop up anytime you did Google search. And I guess, search is changing in a meaningful way. I'm curious, do you have any observations about this content and differentiation and all of that as we maybe move to less tembleau links and more knowledge first in the world that we're operating in?

• 32:59Speaker 01

  Absolutely. Look, I think we talked a little bit about counterintuitive insights. One of the early counterintuitive insights we had when SEO started coming up was that you need to provide value before you can extract value and the value comes from much better content and thus, you know, a whole set of optimization for how do you build content? How do you make it show up in the blue links was formed. Now, I think, you know, AI overviews has completely changed the game and it's no longer about blue links that will direct someone to your website. It is about how can you be where your customers are, not

• 33:40Speaker 01

  just within a search, you know, because AI overviews answers pretty much all the basic questions. And if you still are the subject authority, then you become part of the answers that AI overviews give with the sourcing that then still brings you back. But it's not enough. You now need to go from, you know, search to where your customers are and they are YouTube, they are in LinkedIn, they are in communities. And so, our content diversification strategy has been a few years in the making, from blogs to YouTube to podcasts. I mean, how do people consume information? By listening to you, Logan, and by listening to authorities

• 34:23Speaker 01

  in the fields. And I think we've built a whole podcast network for that reason and email newsletters are still in fashion. So I think customers in this age should have a diversified content strategy, which certainly includes, you know, clear blogs where you are the content authority, but you should also be in All of the places that your customers are.

• 34:49Logan Bartlett?

  Do you have customers coming to you, um, helping inform elements of where to take the AI roadmap? And any interesting lessons from some of the conversations with customers and what people are kind of thinking about and trying to push, push the ball forward?

• 35:05Speaker 01

  We are constantly talking to customers, but more importantly, we're constantly observing the patterns of usage, you know, in AI, right? Sometimes when the technology is well established, you can just go ask your customers what, what they want. When the technology is in an early part of the new curve, you just need to observe and see what is happening a lot more. And a couple of observations.

• 35:38Speaker 01

  When customers are using AI, they're looking for intelligence. And in fact, they're okay with, you know, uh, your AI feature thinking, analyzing, reasoning and giving them a better answer. Versus what you were optimizing in the cloud world, which was just giving them information. So there's actually a pattern distinction that's happening from age of information to age of intelligence. And, uh, what is important within the pattern is the more accurate you are, the more you reason. And the better your results are, the more usage that you get in terms of, um, you know, customers.

• 36:23Speaker 01

  That's a new interesting pattern because you know what? For decades, we've been focused on optimizing millisecond speed, right? Like the latency was such an important concept. Now it's like, you're used to thinking, you're used to waiting for, you know, any of your reasoning models actually thinking and giving you a better result. So that's a different pattern right now. The other pattern that's emerging is that customers want context to follow them across AI features. So think of that, like I'll say, my, uh, tabs look very different now than five years ago. I have Claude with projects open, Gemini with gems open and you know, um, OpenAI with

• 37:03Speaker 01

  deep research open and every one of those, I have the context of what I'm working on in each of those. And if, if I'm putting a prompt in and it does not get the context, I'm like, I'm so annoyed. I'm done with it. And that's the thing that is new within, you know, AI is that the context needs to follow you. So who wants to go into every single prompt and give like a huge context window of things, right? It needs to know what products you're selling, uh, what your value proposition is, how you communicate that value proposition, which competitors you can connect with, all of that context needs to follow. And when you build in a way that context is prevalent across your AI features, you get much better

• 37:44Speaker 01

  usage. And then, you know, the other pattern is there's, there's, there are features that are just neat. And then there are features that are necessary. So we are looking, when we launch a bunch of features, we're kind of like looking at usage patterns to see which ones are going from neat to necessary. Because the neat ones are going to go away, you know, and they're, they're just not going to be useful for customers. But the necessary ones are going to drive repeat usage, repeat value. And that is, you know, what we want to double down on.

• 38:17Logan Bartlett?

  The hedonic or the insatiable element of AI is a funny, I mean, anything, I guess, that we go through in society. But it's funny where you go immediately from like just pure wonder and joy that AI can do these things to like a little upset with it that it didn't switch context with you over the course of, you know, a couple of months. It's like, this is amazing. Best thing ever. Now you're like upset with it. I feel the same way about flying. No, no, I mean, Waymo out here. Whenever I, like, the first time I got into a Waymo, I, it was just pure joy and amazement that we've gotten here and that society's at this point. And then I got one the other day and it was like, uh, it didn't stop near enough to where I wanted it to. And I was like, you've got to be kidding me. I've got to walk a

• 38:58Logan Bartlett?

  block to go get this car. And it's amazing, the human psyche in terms of what expectations change and adjust all this stuff. It's true with AI as well.

• 39:07Speaker 01

  It is true, right?

• 39:08Logan Bartlett?

  People's expectations shift very meaningfully.

• 39:10Speaker 01

  And patterns are emerging, which are just like absolutely fascinating to watch. And yeah, I I probably shouldn't be annoyed at AI. I'm like really thrilled. I'm like obsessed with, you know, everything has changed in my working pattern. Because I have these different tabs and I'm al- always asking questions, but I'm also like, no.

• 39:27Logan Bartlett?

  I know. No, no, it's amazing. To to that then, I guess I'm curious, is there, um, what's what's the single thing that you've adjusted most from a day to day productivity standpoint? Or just like how you how you go about your day work wise from AI standpoint?

• 39:40Speaker 01

  Look, uh, I, you know, I have days when I'm meeting with partners and customers and those days are dramatically different. You know, uh, if I'm meeting a new customer, I go to agent.ai. There is a customer research agent and it gives me what used to take me literally hours of researching and putting briefs or having someone in the team put the brief together. You know, I go to this agent and it gives me everything that I need to know about the customer. So I'm much better prepared. If I'm meeting an existing customer, then I go into, you know, our co pilot, like summarize the company, summarize the contacts, summarize all the last conversations. What were the next steps? What are the objections that these customer is has been talking about?

• 40:23Speaker 01

  And where should I hit all that like preparation? And then you go into meetings much more informed. And you, the prefer preparation time has changed. The depth of conversation you can get to in thirty minutes has changed. And obviously follow ups have changed. So I think my day has changed that way. And then, you know, on uh, everything else in terms of it, it is, you know, I have multiple L L M tabs kind of like open and I'm constantly learning. And most of the time I'm amazed that you can take a topic and research it and honestly go to someone, let's say in legal department or finance or even product and we have an intelligent conversation about it because all the basics you kind of like understand.

• 41:08Speaker 01

  And so the depth of conversations have just, you know, changed pretty dramatically.

• 41:14Logan Bartlett?

  Yeah, deep research is getting, I I I haven't yet been able to use uh, the full building block of like deep research for podcast prep or something.

• 41:23Speaker 01

  Yes.

• 41:24Logan Bartlett?

  It's good, though. It's, I I didn't do it for this episode, uh, but I've done it.

• 41:29Speaker 01

  I'm so disappointed.

• 41:30Logan Bartlett?

  I've done it in prep, uh, just sort of seeing what comes back and how it compares. And it's getting pretty close and you can cherry pick questions from it.

• 41:40Speaker 01

  Yes.

• 41:40Logan Bartlett?

  And if someone has a decent web presence, it's pretty creative in terms of being able to be an assistant or a co-pilot for thinking about questions or different things that are interesting. So it's, yeah, I'm trying to integrate it more and so the productivity hacks are super helpful.

• 41:57Speaker 01

  Yeah, and to me it's like brainstorming, right? It is, I want to say this this way, is there a more creative way to say it? Is there a more compelling way to say it? And how would you say, like, I've put all my podcasts and my LinkedIn posts into one project. And now if I give it some thoughts, it's actually pretty clear. It uses words that I have used before and that's just such a, I mean, it's a delight, honestly.

• 42:27Logan Bartlett?

  Yeah, it truly, truly is incredible. I'm curious, so you came up within sales with a technical background. I guess as you think of the world of selling going forward, what role do you think feels uniquely human? And that is always going to exist in the world of sales versus what do you think can be automated? Or AI can play a good role from an augmentation standpoint? Prep's an obvious one, it sounds like, but.

• 42:57Speaker 01

  Yeah, I mean, look, I have always thought of sales as part art and part science. Science can be augmented and science can just get much, much better with AI. The art of me connecting with you and having a conversation and you trusting me as someone I'm selling something to you and you buy, not just because of the product, but because the value proposition that I communicated to you resonates with you. That is art. Art of getting to know what the customer wants, what their challenges are, what success looks like and how you can help them with that. That is art within within sales and I don't think that can be replaced.

• 43:42Speaker 01

  I do not yet foresee agents selling to agents. Can you imagine an agent selling to a procurement agent and both of them are negotiating? I mean, I don't want to be there. I think it's it's humans selling to humans, but with much more insight, with much more personalized, you know, demos, personalized discovery, personalized solution forming, and I think that is an exciting world. So you you said it like on the science part of it. Of course, you can research companies faster. You can uh discover deeper by asking the right questions. I mean, imagine you had the agent and said, look at similar customers and all the objections and be prepared for all of this. You can you can do that better. You can do the follow ups better. It's also all of the administrative work.

• 44:26Speaker 01

  I mean, I I still remember the decade in sales where I was entering information into fields, which I never wanted to. And then, you know, as I went into management, I forced everybody to enter information to fields. All of that part completely, you know, changes over the next few years. And uh the art still remains.

• 44:46Logan Bartlett?

  You were an accidental salesperson.

• 44:48Speaker 01

  Yes.

• 44:48Logan Bartlett?

  Is that fair to say?

• 44:49Speaker 01

  Yes.

• 44:49Logan Bartlett?

  But you stuck with it.

• 44:50Speaker 01

  Yes.

• 44:51Logan Bartlett?

  So so I guess what what element of of sales as someone that was technically trained and uh thinking they're going to go into product marketing uh but lands in sales? Like what what uniquely appealed to you about it? That you you built a career around it uh ultimately becoming a CEO? But that wasn't the path, the the direct path you took.

• 45:11Speaker 01

  That it. Thank you for asking me a question. Yeah, I uh I got out of business school, wanted to be in product marketing, and I got a job in product marketing at at C-Ball. And then they were like, oh, go and be in the sales organization. The first job I took was a value sales engineer. There was a role and there still is a role called value engineer, but it was about uh communicating the value of technology in financial terms. So I was mostly talking. Talking to CFOs back then, NPV analysis, ROI analysis and really

• 45:44Logan Bartlett?

  Building the case, Siebel comes in, hey, you've, I guess, were there homegrown systems that you were competing with?

• 45:50Speaker 01

  Home, ACT, ACT used to be the system that we used to compete with. This was like well back in those days and then obviously homegrown grassroots, all kinds of, you know, green shoot systems.

• 46:00Logan Bartlett?

  And so you're saying, hey, this is a new product, we have Siebel, but what's the ROI for you switching and what's gonna, like, how much close time or rep saving productivity?

• 46:11Speaker 01

  And what I found in my value selling days is that you can really get deep with a customer to understand their problem. I was not very good in the first five minutes of the sales conversation because that was mostly like banter and relationship. I was like terrified of those first five minutes because I probably didn't watch the game that they watch or I didn't go where they were.

• 46:38Logan Bartlett?

  Go to the golf course.

• 46:38Speaker 01

  Go to the golf course. I didn't do any of that stuff. But the next 25 minutes were about, did you, do you understand their business? Can you remain deeply curious and ask about what the biggest challenges were? Can you then connect it to what you can offer in a way that resonates with them? And then when they buy, did they get promoted? That was like a moment for me where a sale or being in the sales organization was not about selling, but was actually about getting your customer promoted. And if you can look at sales that way, then it becomes deeply fulfilling.

• 47:16Speaker 01

  And I think that, you know, over that next decade, I had conversation after conversation. I was, I was on the road. I was talking to customers a lot. And every time that clicked, every time I could connect deeply to the customer, their problems and then You know, six months later, two years later, they get promoted was like, this is it.

• 47:35Logan Bartlett?

  It's such an important point that the getting the person promoted, maybe can you can you unpack a little bit like why that is an amazing North Star to have and and how that's kind of the the canonical thing that you want to accomplish as a as a software seller?

• 47:51Speaker 01

  It it was, you know, I looked at a quarter after quarter and, you know, getting to a quarter is is nice and it's great, but the moments I felt like I was doing something really unique was I'd go back to the customer, you know, and a year after, two years after, and that they had gotten promoted. And to me, that was my North Star. And I've tried to kind of have that customer centric view in almost every company I've gone to because when you collectively think about customer success and their success in metrics that they choose to you know, focus on their success and what gets them promoted, then, you know, you know, you're not

• 48:36Speaker 01

  aligned on in the short, just the short term, because sometimes salespeople tend to think about the month or the quarter or their annual goal. And the way to optimize it is really to optimize it over the medium to long term, which is why that's a much better North Star. It's also like, you know, that's a that's the way I felt much more fulfilled as someone in the sales organization. And I think that builds deeper empathy for customers. And the deeper empathy for customers then translates into the right optimization. If you know you're going to go back to the customer and have a conversation with them

• 49:19Speaker 01

  one year out, two years out, what decisions will you make today? It's a very different, you know, conversation that you'll have today, knowing that you will talk to that same customer a year out, two years out versus you just sell and then you go on to the next deal, right?

• 49:35Logan Bartlett?

  And it's particularly important because, especially with startups, that person is taking a chance on you. They're putting their neck out there organizationally, saying this is the solution. And so if that's your aspiration, not only is it a fulfilling way of going about your days, that they're ultimately going to get promoted, but it's actually one of the best demonstrations that there was ROI, that the value sale actually was material in that way.

• 50:03Speaker 01

  That's exactly right. And the, you know, when you're in the same industry, doing the same thing for a while, you know that that customer is going to go into the next company. And if you've done a great job for them, helping them, then they're going to bring you into the next company and the next company and the next company. And that is like also super valuable. So I think like, maybe the broader point here is optimize for the longer term, you know, and do all the right things that will get your customer to be successful in the longer term, and then everything else will follow.

• 50:40Logan Bartlett?

  As you've continued to rise within these organizations and managed bigger and bigger teams, I know you've coached a lot of young sales reps, sales managers along the way. I guess as you look back and reflect on the people that have been most successful, that you've worked with within sales, is there a certain characteristic that you think stands out the most, maybe as a through line across the people that have really worked and succeeded that you've been fortunate enough to work with?

• 51:09Speaker 01

  You know, I'd say curiosity is probably the number one thing. And

• 51:16Speaker 01

  Resilience, you know, I look for that. I look for what have you done in your life where you overcame odds? And where have you remained very curious to learn and grow? You know, a lot of sales folks, you know, start with their company, their product, their value proposition. And really, the best ones, the ones that have the art form down, they start with, what is your business like? And what are your biggest challenges? And they get like super deep and remain very curious about the customer's business. That's an art form. Asking the right questions is truly an art form and remaining very curious.

• 51:58Speaker 01

  And then connecting your, you're then taking the mental burden of connecting your product and your solution to a customer's problem versus dumping your entire product and the 100-page deck in a 30-minute format and saying, now you figure out how you're going to take this and, and, you know, use it in a way that changes your business trajectory.

• 52:18Logan Bartlett?

  Resilience, I assume there's, you can tease out examples in someone's background of when they've had to overcome something. Curiosity, I would think, is a little harder to try to interview for or figure out. Is there any way that you've found the best try to tease that out through an interview process or a case study or whatever it is?

• 52:39Speaker 01

  There's the simplest question. What questions can I answer for you? Is literally the simplest question that you can ask in the interview. And you know, it is so interesting. Some people will be like, no, I have no questions. I looked at your website. I looked at your 10K, your 10Q. I have no questions. I'm like, how can people not have questions? That, you know, that is literally the question I ask. And half the times I get very thoughtful questions. And then I know they are curious, they're thinking. And then half the time I get the very basic questions that I know, okay, they've, they've not done their work. And so there are basic things you can do.

• 53:18Logan Bartlett?

  HubSpot's evolved. We talked about the, the culture and how it shifted over time and, and being the organization that you are today. I guess, can you share more about HubSpot's culture code? And how the process of actually evolving works?

• 53:34Speaker 01

  Thermes, you know, wrote the first culture code deck. And I think it's now been downloaded. I would say five plus million times, you know, over, over the years. And the idea is simple. Culture is another product and needs to continue to evolve. And uh, culture uh, is what attracts employees. Just like marketing attracts customers into your company. Culture is what attracts employees into your company. And then it's a living, breathing thing. So over the years, uh, every time we have gone through kind of, you know, big changes and sometimes even not with, without big changes. We have looked at what needs to evolve within the culture code.

• 54:16Speaker 01

  So for example, we went through the pandemic and overnight we went from a Boston-based, an in-office company to a global hybrid company. So then your culture needs to evolve around. How do you, how do you have norms and behaviors in a virtual, you know, hall? Where you're not coming into a space and what is the expectation of how you behave? And how you actually bring, you know, your strengths into that, that space? And that is, you know, the culture, culture code. Like last year, we went through a fairly big, you know, shift in terms of the culture. I think we're still going to this year. We're going to go through another big shift in terms of the culture. Uh, now imagine AI comes in.

• 54:59Speaker 01

  What is forefront in the culture is a growth mindset. You know, because in the, in the next five years to 10 years, anyone who can learn, grow and uh, get AI fluent is going to become a much better employee, a much more successful employee than the ones that don't. So we've been updating our culture code to reflect that growth mindset and the growth orientation that is required to, you know, thrive in, in the current world. And so the process is really ongoing changes to it.

• 55:31Logan Bartlett?

  How would you describe your, your leadership style?

• 55:34Speaker 01

  I don't know, this question always trips me out. I'm like, you know, I don't necessarily think about what my leadership style is, but maybe if you ask people that worked with me.

• 55:42Logan Bartlett?

  Yeah, how would someone else describe your leadership style?

• 55:44Speaker 01

  So they'd probably say, um, I uh, have high integrity. Um, I'm authentic. I expect a lot out of people. I have very high standards, uh, but I also, um. Put in a lot, you know, I don't expect anything that I don't put into the business or to the environment.

• 56:06Logan Bartlett?

  I'm curious, management style, I I heard you say that um maybe initially you you had something like an individual contributor mindset around managing. Can you talk about that and what you had to shift to, what you learned from it?

• 56:18Speaker 01

  You know, early years of being an individual contributor, what is really a key is you're prepared and you have answers. And interestingly, the first time I took on management roles, I took that same mindset and went into being a manager. It's prepared and I had answers. So anytime my team would come to me, I'd be like, Logan, this is exactly what you need to do. And what would you do? You'd be like, no, I don't want to do this because I want to find my own way. So I think the first transition that I had from being an individual contributor to a manager was rough. And I had to learn, you know, two things. One, I needed to slow down.

• 57:00Speaker 01

  I needed to slow down to make sure uh the team was going to go far along with me. And that I'm, you know, I'm kind of like, I have this little bit of an action bias, and so that was hard for me. And the second thing I had to learn was um stop giving answers, you know, but start asking more questions. And um how do you ask questions of your team so that they can think a little bit more about what they need to do? Nobody wants to be given a set of playbook to follow. They want to come to a conclusion about what that playbook should look like. And so I still, you know, I I have a tasks board for me every day.

• 57:40Speaker 01

  But the one, you know, uh piece of the task board which is always there is daily reminders. And the reminders that I have go slow, ask more questions. And, you know, slowed, literally, I have to slow myself down every day. And I think I learned it early. Uh but it continues to be a lesson that I want to get better at applying.

• 58:05Logan Bartlett?

  Workday is known as one of the, it's a canonical software business along with HubSpot. And I think it's known, similar to HubSpot, as having a very distinct culture and strong sort of foundation around that. I'm curious, was there anything that you internalized from your time there that you keep with you and maybe that an entrepreneur listening or an executive listening could bring to bear in their own business?

• 58:39Speaker 01

  Look, almost every company, I've been really fortunate to work with great leaders in great companies and I've learned so much along the way. A couple of things I learned in Workday. One, you certainly mentioned that product was as important as the culture and I think they continue to do that. The other thing, I was working for Mike Stanky, who is the COO and he's phenomenal, continues to be one of my go-to mentors. I probably go to him and ask questions. And the thing that he taught me was how to be data-driven and remove emotions out of decision-making and how to recognize patterns in data. So

• 59:23Speaker 01

  I worked with him for many years and he would say something like, "In God we trust, everybody else bring data." And we all took that to heart and you'd go to him with data, but he would also remember a data point that you probably shared with him six months before. And so, being very precise with the data and using the data accurately and looking at how you apply patterns, that was something that I learned from Mike and I continue to use that. Maybe for startups, I thought one of the things that Workday did really well was even early-stage startup, they thought through

• 1:00:00Speaker 01

  The uh the core foundations of scaling a company. Reasonable amount of processes, um good data, good systems, a common way of getting things done. And I don't see that enough. I've had the opportunity to work in so many other companies. People ignore the basics, which is, you know, is there a basic way to get, you know, work done? Is your data in one place? Do you have basic systems to, you know, do like the headcount process? Or, you know, look at your forecasting in a common way. Startups tend to ignore that. I would say, don't ignore it too long. Uh, because when you scale, and I think now the current generation, the current, you know, cohort of startups are scaling really fast.

• 1:00:43Speaker 01

  Your basic infrastructure needs to keep up, otherwise that's, that is going to slow you down. And that's something that I learned at Workday.

• 1:00:50Logan Bartlett?

  The, the basic infrastructure, as you, as you think about it, uh, what, what are those uh primitives? If you're a founder listening to this and thinking like, okay, I, I got, like, I wanna be, I don't wanna break. I don't wanna go too fast and all this. Are there, are there things that stand out as uh examples? Or um potential choke points that you should just get out in front of uh as a, as a high-growth business?

• 1:01:16Speaker 01

  Logan, we were talking about this, the, the times that we've grown faster than our infrastructure. You know, you don't hire well, you lose out people, and you don't find the right customers. You churn out customers, and that eventually slows you down. So when you think about scaling, you gotta get the people processes, right? Do you know the kind of employee that you wanna hire? Are they clear about the value proposition that you have as a company? Are you onboarding them well? Are you making sure that they are getting the right coaching in the early process? And if you can do that consistently, then you can actually scale.

• 1:01:58Speaker 01

  Then on the customer side, you know, you you again have to have the basic processes. Do you know the ideal customer profile is, you know, can you uh get one salesperson to do the job of ten? Well, in order to do that, the data all has to be in the same place. You should know which, you know, customer profile is going to stay longer and get value from you as a company. That means that information needs to be there. So I think like really asking those two questions of uh can you hire well? And can you retain your employees well? Can you find the ideal customer profile and make sure that you don't churn them out? Those are good places to start with.

• 1:02:40Logan Bartlett?

  Hmm. Are there any companies or anything that you're like uh anything that's that has you excited outside of some of the stuff we've we've touched on? Different company types or um work uh trends or um yeah, anything that comes to mind?

• 1:02:58Speaker 01

  You know, I I literally wake up and sleep uh thinking about AI.

• 1:03:02Logan Bartlett?

  Is that is that right?

• 1:03:04Speaker 01

  Literally.

• 1:03:04Logan Bartlett?

  So you wake up every day thinking about AI, which is exciting. Does this remind you of any trends that you've lived through i- in the past? Or do you think this is more internet, more mobile, more cloud?

• 1:03:16Speaker 01

  What do you think?

• 1:03:17Logan Bartlett?

  I oscillate back and forth. I think one of the things I I think is probably when I think about mobile, it changed the world.

• 1:03:26Speaker 01

  Yes.

• 1:03:26Logan Bartlett?

  In a really meaningful way. Uh, the vast majority of value was captured by incumbent players in some way, shape or form. Uh, and so that being Google and Apple and large part to some extent Meta. Uh, there are still really big businesses built around it. Uh, and that could be Uber or, you know, Instagram now or WhatsApp or Airbnb that weren't possible in the past. And I guess I don't know um if we end up with multiple trillion dollar plus companies, which we we had in the internet world. We had Amazon and we had Google.

• 1:04:00Speaker 01

  Yeah.

• 1:04:01Logan Bartlett?

  We had uh Facebook or all kind of internet vintage businesses. Um, mobile, we didn't really end up with any that were like. Well, you could argue maybe Facebook, but like not really. And so I think it's probably more mobile, although OpenAI certainly seems on the path to being a trillion dollar business. At least it seems that way.

• 1:04:21Speaker 01

  Totally.

• 1:04:22Logan Bartlett?

  But I think a lot of the value is going to be captured by the incumbents. So I sort of go back and forth.

• 1:04:25Speaker 01

  Yeah, tell me more about that. And now I'm like asking you a question, but.

• 1:04:28Logan Bartlett?

  Yeah, that's great. You want to switch seats?

• 1:04:31Speaker 01

  Yeah, I would love to do this. You know, I've always wanted to be on a podcast show host. So do you, where do you think the value is going to go? Is it like incumbents or startups? And how do you, what's your thesis?

• 1:04:41Logan Bartlett?

  I think incumbents, if it's an existing, to your guys, not just to compliment HubSpot, but I think that if there's data centricity for existing processes in some way, I think that the incumbent will get 15 chances and the startup might only get one. And so there'll be some that misexecute on it, maybe making this up as ServiceNow misexecutes on ITSM. And so some new company comes in and I, I think there will be one of the potentially big cloud players. If I think about the businesses of your guys' scale and up, I think that one maybe will misexecute,

• 1:05:24Logan Bartlett?

  but there's probably only 10 of them. And so that means 10 will capture the vast majority of the dollars. And then I think there's a bunch of businesses and processes that are just discreet and totally different. And there isn't some data gravity that already exists around it. And that's where we've been spending a lot of our time in those things. And it could be, I mean, Brian talked about, was it service as a software or something? And, and so I think that was, that was his term originally. But there's definitely a lot of service spend that I think new companies will be able to tap into. And one of the things we're seeing is when you're able to price now. Based on some outcome in some way.

• 1:06:06Speaker 01

  Yeah.

• 1:06:07Logan Bartlett?

  The market's far bigger than the seat-based pricing that we saw in the past.

• 1:06:12Speaker 01

  I mean, I, I, you know, you've been following mobile and social and all of those. I lived my life through the on-premise to cloud and now obviously cloud to AI. I think a lot about the, the changes that needed to happen then, both in terms of the technology, architecture, can, you know, customer behavior and pricing. And then now, you know, what is interesting is that when we went from on-premise to cloud, there was a discontinuous architecture where you needed to go from single tenant into multi-tenant. Remember those days? You were like talking about multi-tenancy. Is your cloud product multi-tenant? Every cloud product should be multi-tenant. So we were going through that and that was discontinuous.

• 1:06:56Speaker 01

  Like you had to do something new in a, in a different architecture. But if you look at where we are now, incumbents, uh, you know, can expand to support a Gentic, you know, uh, AI versus a discontinuous thing. What do you need? You need a lot more data. Great. You can grab a lot more data. What do you need? Better context. Great. You can build that context. What do you need? You need orchestration across all of that, better loops with customers. So you can learn whether an answer was good or not. And yes, you can build that. And you need a, a, a more reimagined UX. And so a lot of like what you need in an AI first world,

• 1:07:38Speaker 01

  the incumbents either have an advantage or can innovate quick enough to get there. Of course it comes down to execution and, you know, that's, that, that's a given. But, um, I'm not seeing like a discontinuous kind of like architectural shift. Now, on the, on the pricing side, uh, again, going from, you know, maintenance and, uh, you know, the, the license models and maintenance model into subscription, discontinuous, right? Because your entire revenue model changed because of that. Here, I do think that future pricing is going to be hybrid. You're going to have some. Seed based stuff and you're going to have a lot more usage and results oriented stuff.

• 1:08:20Speaker 01

  But again, that is not discontinuous. You know, if you take HubSpot today, we certainly have seed base, but we also have contacts and things that are much more, you know, consumption usage based. So we'll expand the number of consumption lovers that we have, but it's not a discontinuous move. So maybe my view, and I think about this every day, is there's a lot that we can do. HubSpot has distribution and speed of innovation. We are innovating like a startup and we have to keep executing in how we innovate. But we have distribution and innovation. We have structured and unstructured data. We have context across the customer journey and functional view and lots of advantages.

• 1:09:04Speaker 01

  Of course, execution wins.

• 1:09:06Logan Bartlett?

  Doesn't it feel like the incumbents, and I would call HubSpot an incumbent, I would call Microsoft an incumbent, a Facebook incumbent, like the material businesses in their category. It feels like they're also far better prepared and just executing at a higher level. And I guess I didn't totally live through the vintage of the on-prem to cloud transition, but there weren't that many businesses that survived.

• 1:09:30Speaker 01

  Yep.

• 1:09:30Logan Bartlett?

  And to your point, it was discontinuous innovation and that. But, you know, there were a lot of businesses that failed that transition. It feels like on the AI side, people are a little bit more prepared and forward leaning and they've read all the books about how to be disrupted.

• 1:09:48Speaker 01

  Totally.

• 1:09:48Logan Bartlett?

  It feels like it's a lot better run companies than we.

• 1:09:51Speaker 01

  If there's a foundational value at HubSpot, it's paranoia. We wake up every day being paranoid and I think it's actually served us well. It's been there even before this disruption cycle. Every day we'll think about how do we serve customers better? How are we going to get disrupted? And so I think there's a healthy amount of paranoia. That was not there. I lived through two on-premise companies as we were going through cloud. And, you know, I had the fortune of being in some rooms where decisions were getting made. And we would talk about how cloud companies were growing very quickly in revenue. Every year we would have a competitive, you know, plot and the size of the bubble for cloud companies would get bigger.

• 1:10:35Speaker 01

  And the conversations were not urgent.

• 1:10:39Speaker 01

  And the conversations were like, yeah, cloud is interesting, but you know what? Our customers want security. They want control. They want to be here. I think you're not seeing any of us operate with any of the, you know, that kind of mindset. We are running as fast and I can tell you about HubSpot. Urgency is so critical and we have multiple conversations a week about what we need to do to innovate. And so that's very different mindset.

• 1:11:05Logan Bartlett?

  Is it because we're, we're more interconnected socially? And so you get, uh, maybe information just flowed a lot slower 20 years ago. And so you, you've heard, oh, we were talking to our enterprise customers and GE said they're never going to go. Or IBM said they're never going to go to the cloud. And so we don't have to worry about it.

• 1:11:23Speaker 01

  Yeah.

• 1:11:23Logan Bartlett?

  And now there's more proof points out in there in the wild and it's happening a lot quicker. Why do you think this, this generation's a lot better prepared for it?

• 1:11:29Speaker 01

  I think we all read the same books.

• 1:11:31Logan Bartlett?

  Yeah. And we're all tightly connected.

• 1:11:34Speaker 01

  We're all, we all read the same books. We know, uh, the, the graveyard of companies that didn't transition. You know, different S curves is filled with, you know, case studies and examples. I think we've all grown up looking at who didn't make the transition. BlackBerry didn't make the transition. Blockbuster didn't make the transition. Every one of these transitions, we've read about those case studies and they're ingrained in how we think about, you know, scaling and growing. And that's one. I think the other aspect is that there is true value in this. At the end of the day, you know, I don't get excited about technology unless there is a clear path for driving value and solving core problems of customers.

• 1:12:19Speaker 01

  And this is so obviously the case. You know, it's so obviously the case that you can do things completely differently with AI in support and sales and marketing and coding, engineering. You can almost do any one of these very differently. And so the, the value is also very obvious.

• 1:12:37Logan Bartlett?

  As you shift that pricing, you, you touched on it. It, it made me think of something. As the pricing shifts.

• 1:12:44Logan Bartlett?

  Do you think that ends up being to HubSpot? Obviously, the value will be a conversation between a customer and the vendor itself. But do you think that overall, the value that AI provides will be an uplift for revenue for all of the businesses that are able to do it well? Or do you think some element of the seat-based pricing? And maybe we talk about composable interfaces and all that. It might be deflationary in some way.

• 1:13:17Speaker 01

  You know, there's this very simple equation of P times Q. And everybody talks about, you know, if the quantity goes down, what happens to price? Right? Even in a world where, let's say, there are fewer, you know, support reps doing their jobs, who's doing the job? Software is doing the job. How do you price software? Based on the outcomes and the results at Deloitte. So that world has like more software. And while it might be deflationary from a seat perspective, the value that you are delivering is actually higher in the future world, which means how you'd be able to monetize that is actually going to increase and improve.

• 1:13:59Speaker 01

  So I, you know, I think the world is going to have more productive people with more useful, you know, application software agents.

• 1:14:12Logan Bartlett?

  Interesting. Well, that's, that's it on my end. I don't know anything else you want to hit? Are we good?

• 1:14:17Speaker 01

  I think we're good.

• 1:14:19Logan Bartlett?

  Thank you for doing this.

• 1:14:20Speaker 01

  It was good.

• 1:14:23Logan Bartlett?

  Thank you for joining this episode of the Logan Bartlett Show with CEO of HubSpot, Yamini Rangan. If you enjoyed this conversation, I'd really appreciate it if you subscribed on whatever podcast platform you're listening to us on, as well as share with anyone else that you think might find this interesting. We look forward to seeing you back here with another great guest next week on the Logan Bartlett Show. Have a great weekend, everyone.