Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Chris Miller

1. 0:00 – 4:15

   Chris’s background

   1. CMChristopher Miller0:00

      ... like the actual s- really small initial growth team. We really had an aggressive mentality, an aggressive approach. And what that looked like was, at the time, a very small percentage of, I think, HubSpot's subscription revenue would be described as like self-service. So we approached the team who owned it and we were like, "Are y'all working on this?" Right? And they were like, "No, we're working on a bunch of other stuff." We were like, "Can we, can we take this?" And they were like, "Sure, if you want it." And so we took it and, like, immediately blew it up. And so that attitude of sort of saying that like every problem is our problem, and, and like radical accountability and like ownership mentality helped us find opportunities that maybe the business wasn't explicitly asking us to solve, but we were able to triangulate why it might be important for the business for us to solve it. And when you do that, like we, we look hungry, so let's keep feeding us, right?

   2. LRLenny Rachitsky0:47

      (Instrumental music) Welcome to Lenny's Podcast, where I interview world class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful products. Today my guest is Chris Miller. Chris is VP of product for growth and AI at HubSpot. Chris started as an IC PM at HubSpot where he helped create their early growth team, and as you'll hear, shifted HubSpot towards one of the most successful product-led growth businesses in history. Seven years later, he leads both their growth and AI teams, and advises founders on product-led growth and growth strategy in general. In our wide-ranging conversation, we cover what it takes to become a successful product leader in tech, what skills the most successful PMs need to build, how to find mentors, why you need to scrape your knees as an early PM, also a lot of great stories and insights about what HubSpot figured out about growth across content, sales, product, market segments, and growth loops. I so enjoyed this conversation, and we could have gone for another hour if I didn't cut myself off, and so I'm really excited for you to listen to this conversation. With that, I bring you Chris Miller after a short word from our sponsors. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth. Thousands of fast-growing companies like Gusto, Calm, Quora, and Modern Treasury trust Vanta to help build, scale, manage, and demonstrate their security and compliance programs, and get ready for audits in weeks, not months. By offering the most in-demand security and privacy frameworks such as SOC2, ISO 27001, GDPR, HIPAA, and many more, Vanta helps companies obtain the reports they need to accelerate growth, build efficient compliance processes, mitigate risks to their businesses, and build trust with external stakeholders. Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC2 and these other frameworks. For a limited time, Lenny's Podcast listeners get $1,000 off Vanta. Go to vanta.com/lenny. That's V-A-N-T-A dot com slash Lenny to learn more and to claim your discounts. Get started today. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions. And bigger impact. Guided by world class programming and facilitation, Sidebar enables you to get focused, tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you could meet them at Sidebar today? Jump the growing wait list of thousands of leaders from top tech companies by visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny.

2. 4:15 – 9:17

   Chris’s role at HubSpot leading Growth and AI teams

   1. LRLenny Rachitsky4:15

      Chris, thank you so much for being here, and welcome to the podcast.

   2. CMChristopher Miller4:19

      I'm so excited to be on the podcast. Thank you, Lenny, for having me. Uh, this should be a lot of fun.

   3. LRLenny Rachitsky4:24

      A huge thank you to Kyle Poyer for introducing us. I've heard so many great things about you from so many great people, and so I'm really excited to be chatting. And I wanted to start with your very unique role that you're in now at HubSpot, and it feels like it might be a sign of things to come for product leaders. Your title, as far as I can tell, is VP of product of growth and AI. Can you just talk about what that is, and how growth and AI relate in the context of HubSpot?

   4. CMChristopher Miller4:54

      I've been leading PLG at HubSpot for, like, several years now, and I recently took on the AI leadership role. It's a special place to be in in that I get to help lead HubSpot in terms of how we should be thinking about building the foundational technology to create AI powered experiences, and then also lead the strategy of how we leverage those experiences to help that B2B business builder be way more successful using our platform than they might have been, you know, in, in years past. So it's a, it's a really cool, uh, intersection point between those two things. There's a lot, uh, a lot we can do there.

   5. LRLenny Rachitsky5:32

      One thing I took away from what you just shared is that you are given these two teams to lead, which aren't necessarily connected, but I think it tells me that you're doing a great job at HubSpot.

   6. CMChristopher Miller5:42

      (laughs)

   7. LRLenny Rachitsky5:42

      And I'm gonna try to pierce through your modesty, and I'm curious, what is it that you think you've done really well or been successful at that got the leaders at HubSpot to decide to give you this other team that feels like an incredibly important, uh, initiative in this time of AI?

   8. CMChristopher Miller5:58

      So when I joined HubSpot in 2016, there was definitely like an element of timing that really worked in my favor. Uh, it was maybe like a year or so after, um-... HubSpot had launched their free CRM, which was like a big, you know, strategic play for them and f- for us, excuse me, (laughs) at the time. And it was meant to be disruptive, but I don't think that there was a fully formed perspective on what was gonna happen after that, right? Like, how are we actually going to get leverage and enterprise value out of this sort of (laughs) e- big enormous piece of free software we just put into, uh, in, into the universe, right? And I think the pedigree of product manager at HubSpot at that time was also, uh, a bit different. Like, there were folks who maybe s- uh, started their time at HubSpot in support and so, uh, intimately familiar with the product and with customers. You know, some of these people had closed thousands of, of, of support tickets. And my background was a bit different. I was actually less of a feature PM and I was sort of more of a growth PM in my DNA. And so I sort of looked at this through a completely different lens and, uh, I, I guess I understood that what, that what we were trying to actually do was product-led growth, but we didn't really have the shared vocabulary to call it that, right? And so I think to answer your question, I think I was just willing to take some risks (laughs) a- and really push for the things that I believed made sense, even though maybe based on the titles, uh, that I had at the time, I, I, I wasn't sort of inherently given a seat at the table and sort of really push my (laughs) way into some of these conversations and then was eventually invited to them, right? And, uh, and, and so just always had an interest in driving a strategy that was a, a, a click or two higher than maybe what my immediate team was focused on, and, and was always curious about how other parts of the business functioned. Like, I used to spend a lot of time sitting on the sales floor, um, just going into the other buildings and talking to other folks working on different parts of the business, and, uh, and that's part of maybe the serendipity that I miss about being in person, which is that you might just discover something from, you know, having a casual conversation with someone at the water cooler. You're like, "Oh, that's an interesting problem. Like, I think my team could help with that." And so you absorb a bunch of context around, uh, how pieces of the business are connected and you can start to really widen your aperture in terms of the size of opportunities that might be in front of you that maybe you would've missed if you would've been so heads down on execution work. Um, and so I think that... If, if, if I had to guess how people might talk about that (laughs) if I wasn't in the room, maybe they would cite that, but it's, it's tough to say.

   9. LRLenny Rachitsky8:34

      Hard to do those, uh, serendipitous water cooler chats in these, uh, remote hybrid times, huh?

   10. CMChristopher Miller8:39

       Yeah. Everything's so scheduled and tightly scheduled, then you're bouncing from Zoom to Zoom and, you know, obviously HubSpot has embraced hybrid and there's a ton of benefit to it. In, in fact, you know, I was a new dad, uh, when I came back to work and my, my son wasn't in daycare. And so it was so cool just to be able to like pop out in, in between meetings and play with him for a few minutes just to go back and... You don't get that when you're in the office all day. So, definitely a lot of upside but certainly it's... You got to be a little bit more creative in terms of the, the serendipitous knowledge sharing, the osmosis learning, and, and just contact sharing that happens more organically when everybody's sharing the same physical space.

3. 9:17 – 12:25

   The story of how Chris crashed a party and pitched his idea around pricing and packaging

   1. LRLenny Rachitsky9:17

      You talked about how some of your early success was taking risks and being in meetings maybe you shouldn't be in. Is there an example or a story that comes to mind of doing that where you kind of took a risk early on being kind of an European at HubSpot and... Or something that worked out really well, surprisingly?

   2. CMChristopher Miller9:31

      (laughs) Uh, this is a funny story. For anybody at HubSpot listening, uh, I, I, I apologize in retrospect for this. But, um-

   3. LRLenny Rachitsky9:40

      I'm excited for this. (laughs)

   4. CMChristopher Miller9:40

      ... there was a time where we were having a lot of debates around pricing and packaging, and, you know, there's... And we'll get into this, but our go-to-market model and sort of, you know, where we play in the, in, in the addressable market create some complexity in the sense of, you know, we're serving different parts of the market simultaneously with a connected unified platform, and so how do you think about packaging and go-to-market? And we were trying to just figure out how to simplify, simplify, simplify, and at the time I was an IC, individual contributing PM, so who am I to sort of have a point of view (laughs) on pricing and packaging? But, uh, you know, the person I was working with, uh, my, my designer, um, her name's Mariah Moscato, she's a, she's in product now. She's excellent. We, we were, uh, part of a triad and we, we sort of both had a similar school of thought in terms of what the pricing and packaging could be. And we were over in Dublin where we have our European headquarters, and there was a party happening at the Guinness, uh, sort of storehouse, and I don't know that we were exactly on the guest list, but we figured out a way to get into the party, and we ran into the COO at the time. And out of the blue, I think he had asked us what we thought about pricing and packaging (laughs) , and it was sort of one of those funny you should ask moments, right? And so we ended up kind of pitching in the midst of pints being sort of handed, you know, every which way you, you turn, this vision for a completely different way we might approach pricing and packaging. And he was, he was pretty intrigued and he said, "Why don't you come to the next executive meeting and, and pitch us on it?" I think that meeting was maybe a couple weeks away and so we looked at each other, we were like, "Uh-oh." (laughs) Not what we expec- not exactly what we expected in terms of I think people welcoming maybe a contrarian point of view at that, at that moment in time. And so we sort of were invited into this meeting with folks that we generally don't get to spend a lot of time with to pitch this thing that swam a little bit ups- upstream, and we ultimately didn't go full steam ahead down that path. I think a lot of elements of what we pitched have made it, made their way over time into HubSpot's pricing and packaging, but it certainly, I think opened the door for us and, and, and for me, speaking for myself, certainly for me, to, uh, be welcomed back into that room in the future a- and to be able to contribute ideas towards important decisions, you know?

   5. LRLenny Rachitsky12:09

      I love that it's another example of serendipity and just running into people.

   6. CMChristopher Miller12:13

      Yeah.

   7. LRLenny Rachitsky12:13

      Also, I think it's a really good example of just how important it is for PMs to be proactive and think ahead and not just kind of rely on, like, people coming to you, asking you for your advice and, like, getting invited

4. 12:25 – 16:52

   Relentless curiosity and other important traits to have as a PM

   1. LRLenny Rachitsky12:25

      to rooms. I feel like so much of a, of success in the product leadership role is just, like, suggesting great ideas, being ahead of where people are and having the answers. Like you had the answer right there in the moment, right? And it's 'cause you did the work ahead of time. Is that something you find as well that that ends up being really important?

   2. CMChristopher Miller12:42

      Yeah. Uh, one of the traits that I look for in PMs that I, that I hire onto my teams, and also when I think back to the people that I've learned a lot from working with over the years, one of the common behaviors or, or, or traits is like relentless curiosity, this like insatiable desire to understand things and a lack of fear in admitting when they don't understand things and being uncompromising and getting the answers so that they do understand. And I think if you can bring that to the table, it's much easier to have an outsized impact on whatever org you're a part of or whatever mission you're working on or whatever team, you know, you may be a member of.

   3. LRLenny Rachitsky13:30

      Are there any other traits, uh, in that list of traits you look for that you think are really important that maybe other people don't focus on?

   4. CMChristopher Miller13:37

      Yeah. Relentless curiosity is, is probably my number one.

   5. LRLenny Rachitsky13:41

      Mm-hmm.

   6. CMChristopher Miller13:41

      My number two would probably be resilience. Specifically if you're working in growth, I think.

   7. LRLenny Rachitsky13:48

      (laughs)

   8. CMChristopher Miller13:48

      If you're doing growth right, right? Like if you're doing product led growth the right way, then you're trying to balance the science of, you know, and sort of taking like a somewhat hygienic approach to validating assumptions and hypotheses with being really ambitious and, and really pushing for the things that are gonna have massive impact for your customers at the end of the day. And when you're doing that, you're gonna fail more than you're gonna be successful along the way, right? And if you're not resilient, that can be really demotivating, right? Like I, I think there's a, a stat that some, you know, growth person put out there years ago, which is that like on average only 20 to 30% of experiments a growth team runs might be successful. So that means like 70 to 80 (laughs) percent of the time you're, you're, you're not putting numbers on the board and you're extracting learnings hopefully that you can apply to the future. But I think if you're not resilient, what I've seen happen is you end up sort of grasping for a win, which can sometimes look like making bets that are too small and too insignificant to matter, right? If, if your sort of primary modality of product led growth work is experiment driven product development and you're hitting more than like 30, 40% of the time, (laughs) you're, you're thinking too small, right? And so that resiliency piece is certainly important in my mind. I think coachability is another one, uh, in, in a s- in the sense that I still think that like the sort of subcategory of like growth product management is still like fledgling compared to PMs working on like platform features. And so even when I'm interviewing folks, I'm not necessarily looking for 10 years of experience doing PLG. I think that's a, it's mostly an unreasonable ask-

   9. LRLenny Rachitsky15:34

      Mm-hmm.

   10. CMChristopher Miller15:35

       ... but it can certainly be taught. And even if you do have, uh, some experience doing PLG work, it's important to know that what that work is going to look like is gonna potentially vary in a meaningful way from shop to shop. And so being coachable and adaptable to whatever the context is of the business or problem space that you're working on, I think is an important trait that I look for in, in, in PMs. And then creativity is so important too. Valuing simple solutions to really hard problems. I think if building the next like super sophisticated widget is the thing that gets you out of bed in the morning, like growth might not be for you, right? Like I think the best growth, like product leaders and g- and growth minds that I've, that I've worked with over the years or have had the, uh, the, the privilege of learning from over the years, like I think the thing that I, that I notice about them is they are almost like ambivalent to the solution (laughs) and certainly ambivalent to like how complex a solution may or may not be, and sort of taking like little to no pleasure or pride in the complexity of a solution so long that it delivers the outcome that the business and your customers need, I think is a, is a really cool trait. And I, I kind of like categorize

5. 16:52 – 22:12

   How Chris broke into product management and advice for others wanting to do the same

   1. CMChristopher Miller16:52

      that under creativity.

   2. LRLenny Rachitsky16:53

      You mentioned this phrase relentless curiosity, and it made me think about a story I read about you where the way you got into product management was you were at some startup and the, the founder was just like, "I've read that the cure to all our problems is gonna be hiring a product manager." And you heard that and you Googled, "What is product management?" And then you asked him, "Can I do that?" And that's how you got into the role. So first of all, is that true? And second of all, is what's your advice to people trying to get into product management and what, any lessons from that experience?

   3. CMChristopher Miller17:21

      So first, yes, that is, that is a hundred percent true.

   4. LRLenny Rachitsky17:24

      Amazing.

   5. CMChristopher Miller17:24

      Uh, that is, that is how I stumbled into, uh, product management. So appreciate all the folks (laughs) who took a shot at me back then. But, um, but yeah, I mean, and this was at a time where I would say product management even as a function was definitely not ubiquitous across tech. Like there was a lot more, at least in the world that I was in, a lot more of like a standard waterfall approach to building products with a lot of like middle layers and engineering managers and really no one who had the job of like owning the problem from a customer's point of view. And so there, there wasn't a ton of content out there, and there weren't even a ton of people in the city at the time that I could really talk to, to, to sort of learn. And so a lot of what I did was scrape my knees (laughs) through the first years and a lot of like painful trial and error. And then, you know, eventually I think there's a lot more energy and, and interest around the, the, around the trade craft and, and the function. And so I think...It's much easier today for someone to learn the fundamentals of, of product management without necessarily needing to do it via, like, trial by fire. My, uh, advice to folks who are interested in, like, breaking into product management specifically is, uh, focus. A few things. One, focus on structure, right? I think, like, there's usually a lower barrier to entry to do product management at, like, a smaller shop, which they might not have as much access to the best talent out there, right? But I think what you may often give up in those instances is, you know, structure to your own sort of professional development and formal training and education, and potentially even the opportunity to work for people who are, like, truly battle-tested and have seen the movie several times-

   6. LRLenny Rachitsky19:06

      Mm-hmm.

   7. CMChristopher Miller19:06

      ... and can actually, like, wisdom share. Because truthfully, it looks different in every company. And so, it, it is one of those functions I do believe that taking, like, a truly, like, academic approach towards, you know, upskilling has, like, fairly diminishing returns, because it's, it's tough to field curveballs in a classroom, right? And so, choosing where you want to break in is, is, is almost as important as choosing that you want to break in in the, in the first place. Like, thinking about who you're going to be reporting to, thinking about what's the track record of success for people at that company breaking into product management, trying to think five years in advance and work backwards, I think are all sort of important thought exercises along the way. I would also say that if you're already at a shop, you know, where you are working in a different function and you're sort of, like, product curious, right, like go, go talk to the PM. (laughs) Like, literally what I say is, like, "Go reach out to a PM and ask how you can make their day easier." (laughs) Figure out what you can do in those, in your spare time that they can offload to you and, uh, do a little bit of volunteer labor, even if that's just shadowing, right? Because I think just getting that context and understanding the sort of rhythm of how a team, uh, ideates and defines problems and prioritizes and ships software is the experience that's going to be the most important, because a lot of product management is also managing personalities and figuring out how people want to work with you and figuring out how you work for them. And so, you know, just, just getting that hands-on, you know, hands-on experience or at least direct sight line into sort of the day-to-day of a team is, is really important, because the extent to which you can understand their problem space and understand the things that keep them up at night, you can be valuable. And then, you know, at the very least, what you get out of it is hopefully an advocate, right, or a sponsor at the end of the day who is willing to, uh, gamble some, some professional and, you know, political capital on you to get your foot into the door, even though you might not have any formal experience on your resume.

   8. LRLenny Rachitsky21:04

      There's so much stuff that super resonates there. One is that I always think of, like, the bare minimum job of a PM is just to be useful to people on the team-

   9. CMChristopher Miller21:11

      Yeah.

   10. LRLenny Rachitsky21:12

       ... and help them do better work. And, like-

   11. CMChristopher Miller21:13

       Yeah.

   12. LRLenny Rachitsky21:13

       ... if you do that alone, people are gonna love you.

   13. CMChristopher Miller21:15

       Bring the donuts, right?

   14. LRLenny Rachitsky21:16

       Bring the donuts. Exactly. Yeah. I had Ken on the-

   15. CMChristopher Miller21:19

       Gosh, I'm, I must be old. I don't know that anybody uses bringing the donuts anymore. (laughs)

   16. LRLenny Rachitsky21:21

       No, we had Ken on the podcast. We talked about it. We asked him, like, what is the digital version of that when everyone's-

   17. CMChristopher Miller21:26

       Right.

   18. LRLenny Rachitsky21:26

       ... working remote. I think that's something that even if you're a brand-new PM, you come across soon enough. And then the other piece there, I really love this metaphor of scraping your knees, because I find that to be so important to becoming a PM, is you think you could just, like, read these things, take some courses, and it's gonna go, you're gonna got, you got this and you're not gonna mess up. But I find that messing up is so important in helping to learn to do the job, 'cause like you said, there's relationships and people and changing plans and leaders and it's just like, you're not gonna get it right. And you learn how to deal with all these things by messing it up. So I super agree with that. And even, even though you said it's easier not to learn to be a PM, it's still, I think, important to scrape your knees a number of times for you to actually learn to do the job.

   19. CMChristopher Miller22:11

       Mm-hmm.

6. 22:12 – 26:30

   Helpful tips for learning the craft of product management

   1. CMChristopher Miller22:13

   2. LRLenny Rachitsky22:13

      Along those lines, what did you find was most helpful to you to learn the craft of product management in the first few years? What do you think back to, like, oh, that was really helpful, other than just doing it, messing up, sometimes getting it right?

   3. CMChristopher Miller22:26

      Yeah. So my first product management sort of, like, job/mission was working on a B2B2C product, and there's a lot of unique challenges that came with that. You know, our customer was not the end user of our product. We sold into institutions who then white-labeled our product and then resold it to the end customer. And so at the end of the day, our customers owned the relationship with the end user and not us. And so the challenges that that created were that there was a lot of distance between us and the voice of the customer, or try the voice of the end user, and we ended up building a lot of things to satisfy the buyer and the customer, but not necessarily the end user. And that's challenging, because you don't necessarily know whether you're building something to get a contract signed or you're building something that's gonna delight the, the person using it at the end of the day or provide sort of, like, magical value. And so I, I think I probably shipped a lot of bad product those years, (laughs) if I'm being completely honest. Like, I don't know that I would look back at what I shipped back then or what we, what we shipped back then and sort of say, like, you know, they were the best possible solutions or best possible product. It wasn't until I got my second product management job where it really was an inflection point, where I was like, "Oh. Got it. This is what this is supposed to look and feel like."

   4. LRLenny Rachitsky23:57

      Where was that? Was that at ?

   5. CMChristopher Miller23:59

      Uh, I was, I was, I was, uh, working at a fitness technology company, and the person who really, I would say, changed my entire paradigm of what product management is supposed to be, someone I, I know you know, Farid Mostafa, who I believe was on the pod, uh-

   6. LRLenny Rachitsky24:16

      Ooh, absolutely.

   7. CMChristopher Miller24:17

      ... last October. Uh, shout out to Farid if you're listening.

   8. LRLenny Rachitsky24:20

      Love Farid.

   9. CMChristopher Miller24:20

      Farid is a good friend and mentor and-

   10. LRLenny Rachitsky24:22

       Amazing.

   11. CMChristopher Miller24:23

       ... you know, really-... helped me level up. And what was interesting about those years is it was the first time I'd really gotten to work on a product where it was a freemium B2C run, you know, run tracking app. And so we, we spent a lot of time talking to users directly and like a lot of like guerilla user research techniques, like literally sometimes going outside and just like talking to runners in passing to, to understand sort of like what were the challenges in finding motivation and sort of why do they choose, uh, running assistance, running applications in the first place. And you know, so just that, that having that deep connection to the customer and not feeling like you're being kept at arm's distance was, uh, was eye-opening. (laughs) I was like, "Oh, I didn't know that it could be like this." And then the second thing that we had at our disposal that was, changed the game for me was access to a huge user data set. And so having data at scale to drive decisions, being able to know that if we make a change, uh, we can prove causation, uh, from like a business impact standpoint or a customer delight or, uh, engagement standpoint. And so it was almost like I didn't realize I was blind until... or you didn't realize you weren't seeing in color. It's like that scene in The Wizard of Oz where, you know, they, they land on Oz, and all of a sudden everything's in Technicolor, and you're like, "Oh, my gosh. Like, I can actually make informed decisions about what I'm shipping," right? And, and, and having like a level of rigor around that and really being forced to articulate a hypothesis and have a point of view on what the outcomes might be before you actually build something were all sort of, um, I would say behaviors and just like a philosophy around product discipline that I learned from Farid and that like group of folks that, uh, I worked, I, I worked with closely during those years. And that was I think the... I, I consider that to be when I really became a product manager.

7. 26:30 – 29:34

   Why you should talk to customers, former customers, and potential customers

   1. CMChristopher Miller26:30

      (laughs)

   2. LRLenny Rachitsky26:30

      There's two things I want to highlight there that, again, super resonate. One is just whenever I talk to customers, I always like re- I'm like, "Why don't I do this more often?"

   3. CMChristopher Miller26:39

      Yeah.

   4. LRLenny Rachitsky26:40

      Because every time it's like, "Wow, I had no idea how big of a problem that was."

   5. CMChristopher Miller26:44

      Yeah.

   6. LRLenny Rachitsky26:44

      "Why didn't I do... Why don't I do this all the time?" And then you don't again, and then you do it months later and you're like, "Oh, my God. I learned so much again." And so I think it's just if you're listening, you're just like, maybe just go talk to a customer today and-

   7. CMChristopher Miller26:55

      Talk to customers and, you know, you, we also learned a lot from talking to people who we wanted to be customers but were not, right?

   8. LRLenny Rachitsky27:02

      Mm-hmm.

   9. CMChristopher Miller27:02

      And people who had either broken up with our product, uh, or, uh, evaluated it and never fell in love with it in the first place. And so I think every PM struggles with, you know, time management, and it feels like you need 60 hours in a day to get through your weekly checklist, or 60 hours in a week, excuse me. But, um, finding time to just talk to people. Like even today, like I, I have a lot of friends who are entrepreneurs or small business owners, and some use HubSpot, some don't. But I usually tend to really enjoy my conversations with people who decided not to use HubSpot and to really try to unpack what drove that decision. Was it as calculated as I think sometimes we can all, uh, maybe assume that some of these decisions are? And then you often learn that like there's sometimes kind of emotional, (laughs) like really instinctual and visceral and maybe connected to brand more than they're even connected to product. And there's a lot of like things that I think when you're in the, the, the proverbial like digital conference room with your team trying to understand what makes your users tick, you're just like, "Well, we're actually just, we're illogical humans at the end of the day at our core," right? And like that all rides on decisions people make in the day-to-day, and it doesn't change necessarily when they're engaging with your product as much as we'd love it to be perfect science so that we can, you know, uh, moneyball the system if, if you will. (laughs)

   10. LRLenny Rachitsky28:23

       That reminds me of a story where we were doing some user research on a booking feature within Airbnb, and we went to Paris to do these really in-depth user research studies. We were like behind one-way mirrors and all that stuff, and we were trying to figure out why hosts weren't connecting Facebook to their account. This is like, I don't know, five, six years ago. Because they gave them so much access to where their friends are traveling and reviews and all these things. And especially in France, they were just like, "I don't trust Facebook." And this was before it became a big thing in the US. They're just like, "I don't trust. I don't want them to have any of my data." But like, "Look at all this power you get." Like, "No, I don't care. I don't trust it." And-

   11. CMChristopher Miller28:58

       Yeah. There's a... Yeah. That's why talking to customers is so...

   12. LRLenny Rachitsky29:02

       ... what they can do.

   13. CMChristopher Miller29:02

       Like you could have all the, you know, usage data in the world, and that's gonna tell you what's actually happening in your product, but it doesn't tell you why, right? Like, it'll never explain the why behind a behavior that, you know, you can track through events firing. And so that's why that sort of proximity to the cl- the customer and, and that directing that sort of relentless curiosity towards the, the sort of qualitative stuff is so, so important because you just learn things that are just sometimes really unintuitive (laughs) for, you know, our blind spots because we're often not the people we're building product for.

8. 29:34 – 34:02

   Mentors vs. sponsors, and advice for finding people who will help you grow

   1. CMChristopher Miller29:34

   2. LRLenny Rachitsky29:35

      Absolutely. I want to shift talking about HubSpot the business, but one more last thing I wanted to highlight from what you just shared, which is a really good insight, is you shared that your biggest inflection in your career was a, a manager, Farid in this case, who helped you kind of learn the craft and develop your skills, and that's the exact experience I had too. Just like one specific manager changed everything for me, and that feels like a recurring theme to a lot of people, just having one person that really spends the time to help you learn and correct you when you're making mistakes and all that. So if folks are wondering maybe, "Why am I not learning enough," or, "Why is my career stagnating?" see if you can just find... You know, easier said than done, but oftentimes it just takes one person to change everything.

   3. CMChristopher Miller30:15

      It gets into sort of a conversation about, you know, the difference between a manager and a mentor-

   4. LRLenny Rachitsky30:20

      Mm-hmm.

   5. CMChristopher Miller30:20

      ... versus a sponsor and an advocate. Mentors are great. Don't get me wrong. I have a ton of people that I would consider to be mentors, but when I think about the people in my life who... the time that they-... donated to me, the time that they volunteered to me and, and, and for me. Calling them mentors, I think, s- uh, it sells what they were very short. And I would actually describe those folks as being like sponsors and, and advocates. People who are willing to put up capital, right? Whether that's professional, social capital to, to bet on you. I mean, truth be told, m- when I interviewed, uh, with Farid that first time, I think back to the interview and I think I bombed it. I don't think I (laughs) actually don't think I would have hired me back then. I actually think-

   6. LRLenny Rachitsky31:06

      Wow.

   7. CMChristopher Miller31:06

      ... and I remember the answers I gave to some of those questions and I don't think that... I think they were good but I don't think they were certainly great.

   8. LRLenny Rachitsky31:11

      Hmm.

   9. CMChristopher Miller31:12

      And, uh, and, and if... and I imagine that there was something in there where the decision-maker who was Farid said, "I think I can make something out of this," right? And I think being willing to invest in someone and finding people who are willing to invest in you is what really matters. And finding people who are willing to, to, to again, put something up for you, whether that be whatever kind of capital it is. When I think about true gasoline on the career fire, it's finding mentors but it's also finding sponsors and advocates.

   10. LRLenny Rachitsky31:48

       Is there anything that you think you did right to help find mentors and sponsors and advocates for people that are thinking about like, "Hey, that I, I want... I need this. How do I help myself in the same way?" Is there something you did that helped people get excited to help you?

   11. CMChristopher Miller32:02

       Something I think I certainly continue to work on, but really putting ego aside and embracing not knowing stuff (laughs) and embracing not being good at stuff, and not feeling self-conscious about that. And letting the desire to be the best at something or be... or at least be great at something overpower the fear of being inadequate at something. And, you know, I, I, I played sports growing up and so I, I, I like being coached. Like I can take hard feedback and I like it because if I get better feedback than the people I'm competing against, I, I think I can beat them, right, over time if I work hard enough. And so I think just like taking that mentality with me into product management I think has helped me build bridges with people who don't owe me anything, right? People who don't necessarily need to be invested in, in me, uh, at all, but who might get delight out of it somehow, (laughs) you know? And I don't know exactly how that works and, and the calculus that goes on in folks' brains, but I, I... at least that's... What's within my control is like how I can show up in those... in the, in the context of those relationships and, and sort of really embrace even the hardest, like, ugliest feedback (laughs) and, and, and hope that I can extract something from it that'll make me better at the end of the day.

   12. LRLenny Rachitsky33:22

       I love that advice. Makes me think about Jules Walter's advice, which I've referenced many times on this podcast now, where his tip is when people are giving you feedback, just be like, "Thank you so much for that feedback," even though you're melting inside and just sort of completely disagree with what they're telling you. (laughs)

   13. CMChristopher Miller33:39

       Yeah. Shout out, shout out Jules. Jules is also someone who, uh, has been generous with me in the past in terms of giving time when I've, when I've needed help with stuff. So, ha-... Also a great episode you did with Jules.

   14. LRLenny Rachitsky33:51

       So many people have said what you just said about Jules, about how helpful he's been to them, so clearly a class act, that guy. Maybe we'll have to bring him back.

   15. CMChristopher Miller33:59

       Would love that.

   16. LRLenny Rachitsky34:00

       Yeah. Me too, Jules.

9. 34:02 – 36:07

   What makes HubSpot unique

   1. LRLenny Rachitsky34:03

      So let's shift to HubSpot the business, which is a pretty incredible success story. Eh, from what my notes, it's worth something like 30 billion dollars now as a business. It's been around for 17 years. Still growing, I think, something like 30% year over year. And most interestingly, Okta put out this really interesting report recently where they looked at their data of what tools people are using to authenticate with and they, they show that basically HubSpot is maybe the fifth fastest growing software product in the world. I don't know if it's true, but feels true 'cause all the other companies make sense there. So you don't have to confirm or deny this, but clearly things are going great at HubSpot. I'm curious just what makes HubSpot so special and unique and successful, that's specifically unique to HubSpot versus other companies.

   2. CMChristopher Miller34:51

      There's a lot in there. I ca- I c- I can speak to the things that have resonated most deeply with me in my time there.

   3. LRLenny Rachitsky34:58

      Yeah.

   4. CMChristopher Miller35:00

      The first is legitimate customer obsession. It's not marketing, it's, it's legitimate, right? Like I've, I've witnessed fierce and passionate debates internally that the root of what the people in the debate were really trying to unpack was what was the best thing for the customer. And so really having that be central to our dogma and, and, and how we think about the business and, and, and, and why the company exists in the first place, like really walking the walk there is something that I don't f-... I don't know that that's true everywhere, right? I mean, I've certainly worked at places where that hasn't been true and there's a lot of factors that can lead to those trade-off decisions at times. Like is this the right thing for the business or the right thing for the customer? Being really challenging and I think just sort of having that, uh, customer-centricity really baked into the DNA of the company makes those decisions maybe not easier, but at least you can have more conviction around the why behind the decision at the end of the day. Another thing that I think makes HubSpot-

10. 36:07 – 40:23

    Customer obsession in action

    1. CMChristopher Miller36:07

    2. LRLenny Rachitsky36:07

       Before you actually move on to the next one, I wanna spend a little time on this one because I think people hear this and they're like, "Yes, okay. We're gonna be customer obsessed," and then you have to make these hard decisions. Look at this experiment. It's gonna grow things or revenue 1%, but it's not like really gonna make the customers' life easier. How do you actually make this real? And is there maybe an example where you have to trade off growth versus like we need to make sure the customer is getting what they need or making the customer happy to make it a little more real even?

    3. CMChristopher Miller36:34

       One, I think that's a, uh, a really fantastic, uh, maybe not counterpoint, but thing to call out...My point of view here is that oftentimes it's a function of what's the time horizon that the company uses as their sort of baseline for assessing decisions, right? And typically when you're making decisions that could be described as, like, hostile towards your customers, but are net positive for the business, you're probably not thinking long term enough, right? Because there's no possible way, unless you are completely cornered to market and there is no competition whatsoever, that you could continually be hostile towards your customers and, and grow, right? Like at some point, that's gonna catch up. And so oftentimes, I think it's the tension of what do we need to do in the short term to survive, versus long term, like where are we going, like what's the chart- what's the path that we're actually charting is I think the true tension. But if you're making decisions that might have, like, lasting impact that are customer hostile, like I think that's a really dangerous path to kind of go down. And so having the, I think the, the discipline or the, the, the bravery or the courage, whatever, to, I think, focus on not necessarily tomorrow or the day after and really think about, like, you know, two, three, four years from now, like, what are we, what, what are the outcomes we're trying to drive and what are the decisions we need to make in the interim that are gonna lead to that outcome? If you stick to that sort of framework or first principle is a better way to describe it, then I, I think you'll often end up arriving at the conclusion that doing the thing that's right for customers at the end of the day is the right decision.

    4. LRLenny Rachitsky38:24

       Is there something in the way you operate that helps you systemize that, like in your experiment plan or product specs or experiment results? Or is there a story of something where you just, like, shipped something that shows this customer obsession to make it even more concrete for listeners?

    5. CMChristopher Miller38:42

       Y- there's definitely structure you could put around customer centricity, and I think a lot of it for, for growth at HubSpot and the teams that I lead, it's around, like, forcing specificity of language. Uh, so for example, you know, you look at, like, a lot of standard documentation for features or experiments, whatever, and, you know, one of the first things that's like, outline the problem. I don't know that we even talk about problems without a qualifier. Like, are we talking about a business problem? Are we talking about a customer problem? Are we talking about a, an efficiency problem, right? Like, describe the nature of the problem and parse it out. Because if there's, generally like speaking, if there's a business problem, right, you, you might do the thought exercise of asking, like, "Well, why hasn't that problem solved itself?" Like, what's the actual customer problem that is leading to the downstream, like, negative thing that's happening to the business? And if we can actually, like, create some daylight between those two things conceptually, we can avoid making the mistake of trying to solve a business problem in a way that leads to a bad outcome for the customer at the end of the day. And I think also creating a system that makes it easy for PMs to call out assumptions that they might be making. So if we do this, like what would you predict to be some of the derivative sort of downstream things? And if we can kind of like call those things out and just ki- keep asking, like, "Why, why, why?" to sort of justify some of the direction you want to go in, and then keep asking, "What, what, what?" in terms of what's the sort of like true blast radius and domino effect of these decisions, um, is the approach that we, we take at HubSpot in the tea- in, in my teams at least.

11. 40:23 – 42:10

    How staying in the mid-market space has benefited HubSpot

    1. LRLenny Rachitsky40:23

       Awesome. Okay. So I cut you off in this one (laughs) bullet point so far, so let you keep, let's keep going.

    2. CMChristopher Miller40:29

       Yeah. So, uh, we're talking about things that make HubSpot special, so customer obsession is definitely one. I think where we play in the market too, like, you know, uh, being a company that has been comfortable sort of staying in the mid-market, SMB mid-market space, and, like, resisting the temptation to, to, to try to crawl up into enterprise software, I think makes us special. And, and one of the things is actually, like, really straightforward, which is that, you know, a lot of enterprise software companies, a lot of your revenue is tied up in, like, a small su- subset of customers. And I think what can happen there is that those customers decide that they want you to build something and they're willing to sort of threaten their business over it, then you'll end up building it. And y- is that necessarily the thing that is gonna serve all your customers best? Probably not. Are you gonna end up having to build and maintain bespoke software for one customer? Probably. And don't get me wrong, I think there's a lot of product folks out there who enjoy that modality of work. I'm not one of them. (laughs) Uh, and, and so by playing in the mid-market, it means our revenue is distributed more evenly across our entire install base, which means that there's no single customer who can hold us hostage really. But, but what that does is, uh, you know, with great power comes great responsibility. I think what that does is a forcing function of ensuring that the decisions that we make are a net benefit for the largest swath of customers possible. And I think it really is a guiding light behind some of our decisions around, like, connected experience and, uh, usability and user experience. Um, and, and so playing in the mid-market I think a- affords us to be able to do that. Uh, so I think that's another thing that makes us special for a company, like, of our size.

12. 42:10 – 45:10

    HubSpot’s culture code

    1. CMChristopher Miller42:10

       Culture is another one, and, you know, I won't get into The Culture Code. I think a lot of folks have probably read it. If not, go check it out. But, um-

    2. LRLenny Rachitsky42:17

       I don't, I don't, I don't know if people have heard of that. What is that?

    3. CMChristopher Miller42:20

       Yeah. Dharmesh, uh, you know, our co-founder, one of our fearless leaders, Dharmesh, uh, one of the things he most famously did early on is he published the HubSpot Culture Code externally. You can Google it and find it, uh, anywhere. I think a lot of companies have sort of replicated that over the years. But by being sort of like really open and transparent about the culture both internally and externally, I think, one, internally it creates, like, alignment and it gives everyone something to point to...... to sort of enforce, like, why do we, why did we choose to work with each other the way that we work with each other, right? I think it also helps in attracting the right type of candidates because we put it out there, we're sort of really open about it. If you don't like that culture, chances are you probably won't be super excited to work here. But if that's something that you're craving, and, and I think a lot of quality people crave a lot of the things that are sort of codified in our culture; humility, empathy (laughs) , uh, adaptability, remarkability, transparency are sort of all things that I think people take quite seriously. And so being really open and honest about that, and, and being willing to sort of pressure test it on a regular basis, like, is this still the company we want to be? We've, we're growing really fast. Like, what has changed? What conditions are still able to be supported with the culture we have codified today? What amendments might, might we need to make in terms of who we want to represent, uh, ourselves to be to our customers and, uh, how do we want to work with, with each other? And investing in that, like, in, like, like hiring really good people that can help us scale that, I think is something that makes HubSpot really special.

    4. LRLenny Rachitsky43:52

       Amazing. I'm reading the culture code (laughs) -

    5. CMChristopher Miller43:54

       (laughs) .

    6. LRLenny Rachitsky43:55

       ... on the side here, and there's these little quotes that are really sweet. Like, uh, I really like this one. "Solve for the customer not just their happiness, but also their success."

    7. CMChristopher Miller44:03

       Yes.

    8. LRLenny Rachitsky44:05

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13. 45:10 – 47:36

    Fun rituals at HubSpot

    1. LRLenny Rachitsky45:10

       Is there anything really fun about the culture, like a fun thing that y'all do that's like quirky HubSpot ritual?

    2. CMChristopher Miller45:17

       Yeah, there's a ton. Although, you know, I think, like, there's definitely a very legitimate school of thought around how, like, culture can both contribute to inclusion, but also be a headwind to inclusion, right?

    3. LRLenny Rachitsky45:33

       Ooh.

    4. CMChristopher Miller45:33

       Like, I think a lot of the things that I might associate with, like, HubSpot culture are very much rooted in a specific period of HubSpot, right? It was probably a pre-pandemic period, it was probably a period where we were all sort of working in the same physical space, and so there's a lot of, like, inside jokes, and sometimes the, the, the things are rooted in very specific quirks of specific individuals who may not even be at the company anymore. And so if you're someone who's joined the company in the past, like, two or three years, and that flies over your head, I think we have to ask ourselves, like, what's the value of continuing to embrace these things, right? And so I think what we've been doing over the years is sort of taking inventory of the things that, like, might have been considered part of, like, HubSpot legacy culture and really trying to, again, pressure test it. Like, does this continue to serve us today? And if not, like, we should be really comfortable of letting it go. (laughs) But one of the things that I think is, like, super dope that we do, is we do this thing called Peer Week, which was something that popped up, uh, during the pandemic. And the TLDR is that, uh, it's, it's kind of like a, an event for product and engineering, where, you know, travel kind of changed with the pandemic and, you know, people don't get to see each other in person as much, but, uh, there's a couple weeks in the summer, uh, in, in June where we fly everybody in, either if you're, if you're in North America, we fly you to Cambridge. If you were in, uh, Europe somewhere, then we fly you to Dublin, and we kind of spend a week together. And there's, there's not a ton of focus on just like classic productivity. There's like a ton of focus on building connections and like safety, and just like getting to know people and who they are as like, as human beings. But also like, damn, like I forgot how much I miss whiteboarding and just (laughs) actually being able to get in a room-

    5. LRLenny Rachitsky47:10

       Mm-hmm.

    6. CMChristopher Miller47:10

       ... with a physical whiteboard with people and work on some stuff. And so this is, uh, I think the second year in a row, or second or third, I don't, whatever, pandemic years have really fogged the brain-

    7. LRLenny Rachitsky47:20

       (laughs) .

    8. CMChristopher Miller47:20

       ... that we've done it. And it's like the, one of the things I look most forward to every year is getting everybody in the same city to just hang out.

    9. LRLenny Rachitsky47:27

       I love it. I keep, uh, peeking at these highlights, and they're really interesting. So we're going to link to this, uh, culture code also in the show notes if you want to check it out. But anyway,

14. 47:36 – 55:00

    Key elements that contributed to HubSpot’s early growth

    1. LRLenny Rachitsky47:36

       let's focus on how HubSpot grows. And there's kind of two parts. In my mind, there's just like, how did it start and what worked really well? You're actually on the, uh, inaugural team, I believe, of HubSpot's growth team, and things worked out. Well done. I'm curious, maybe just to start, what you think you did so right early on in the history of HubSpot to help it grow into the behemoth it has become? What was kind of the early success elements that were key?

    2. CMChristopher Miller48:02

       I would say the, the early years of doing freemium. And, and, and for the record, there's definitely, like, a, an iteration of the growth team before I joined that, you know, really, like, Brian Balfour was the person who, I would say injected that first dose of, like, PLG DNA into HubSpot. So shout out to Brian, want to make sure he gets the credit that he's owed.

    3. LRLenny Rachitsky48:26

       Yeah. We're gonna have him on the podcast at some point. It's, it's in the works.

    4. CMChristopher Miller48:29

       Yeah. He's a legend. Brian's great. Um-

    5. LRLenny Rachitsky48:30

       Yeah. Absolute legend.

    6. CMChristopher Miller48:31

       And, and so, you know, after Brian had left HubSpot, you know, it was a bit start and stop. And so when I joined and, and we sort of took another stab at it, I think there are a few things we did. One, in the beginning, is we really...... had an aggressive mentality, an aggressive approach. I think that and- and by my- and by we, I mean the team, like the actual s- really small initial growth team. We tried not to be pedantic about where we were spending our time, and so we sort of tossed our mission and charter out of the window. We said, "Cool." Maybe on paper we were, I think, like the sales tool activation team. It's a very, like-

    7. LRLenny Rachitsky49:12

       Mm-hmm.

    8. CMChristopher Miller49:12

       ... you know, boutique, uh, mission and- and remit compared to like, I think a lot of the other teams at HubSpot's missions and remits at the time. But even though that's what we were supposed to be working on on paper, we were sort of like, uh, if we find something that looks like an opportunity and no one else in the business is thinking about it, we're just gonna try to fix it, right? We're gonna ask for forgiveness rather than permission and- and- and start to call some plays. And what that looked like was, uh, at the time, a very small percentage of, I think HubSpot's subscription revenue would be described as like self-service, like people putting in their credit card and buying something. It was- it was predominantly product-driven, like leads, like PQLs. And so we were literally sending everything to the sales team, which, you know, we're- i- it was laying revenue, but certainly opportunities for efficiency because it was the first time we'd really had a product, uh, at a price point that could be transactional and not a- a- a highly considered purchase. And so we were thinking about this and we were like, "Well, how do," like, "how does this work?" Like, "Is there even a pricing page in that- in the product that people could, you know, f- like actually buy something?" And we found it, but it had been neglected. It was sort of like, I think no one was sort of committing any codes to that repository. So we approached the team who owned it and we were like, "Are y'all working on this, right?" Like, "Is- is this ac- is this an active development?" And they were like, "Nah, we're working on a bunch of other stuff." We were like, "Can we, can we take this?" And they were like, "Sure, if you want it. Like (laughs) take it, like it's one less code base for us to maintain." And so we took it and immediately blew it up. We redesigned the whole thing, focused on discoverability, like how are people getting on this page? Focusing on desirability, like how are we talking about the value props of the things that we're wanting to sell to customers to help them grow better? And then thinking about doability or usability, like how do we actually just like remove the friction that's standing in the way? And so we- we- we did like a mad dash towards this outcome we wanted to drive. And when we released it, it worked, right? Like it actually- it was actually like a step function change in the way that the physics of the- the business and the funnel really looked. And I think that was probably a catalyst moment of everyone saying, "Oh, whoa. There- there might actually be something here." And so that attitude of sort of saying that like every problem is our problem and- and sort of being willing to like really take like a- a mentality of like, I think like radical accountability and like ownership mentality helped us find opportunities that maybe the business wasn't explicitly asking us to solve, but we were able to triangulate why it might be important for the business for us to solve it. And when you do that, uh, I think the business, a- a- a business may get more comfortable putting more on your plate, right? And so (laughs) it's like, "We- we look hungry, so let's keep feeding us," right? And so, you know, over time our remit expands and there's other things that we think are opportunities to gain leverage for the business or deliver, uh, delight to our customers in a more efficient way or in- and honestly, in a way that they probably expected to engage with us at that point in time. Like, it was quite odd that there were so many humans involved in every stage of the customer journey and some of our core customers just like, "I just want to be able to try the thing and like buy it if I want to be like. I really don't want to be forced into a sales engagement," right? And so it was really kind of like meeting the expectations of the modern software buyer in many ways.

    9. LRLenny Rachitsky52:41

       That sounds incredibly (laughs) important. Basically, your team turned HubSpot into a very product-led growth business, which feels very important in the history of HubSpot's growth.

    10. CMChristopher Miller52:51

        (laughs)

    11. LRLenny Rachitsky52:51

        Would you consider what was there before where it was like the beginnings of self-service, but they had to talk to a salesperson? Would you consider that product led?

    12. CMChristopher Miller52:58

        Yes.

    13. LRLenny Rachitsky52:59

        Or s- okay.

    14. CMChristopher Miller53:00

        Yes.

    15. LRLenny Rachitsky53:00

        And so w- how would you describe what the shift was in terms of the way the sales motion and growth motion changed?

    16. CMChristopher Miller53:06

        The go-to-market motions that we were working on definitely fit under, I think, the broad umbrella of PLG, but I don't think the culture of the company was necessarily explicit about like being a PLG company. I don't think that's the way we talked about who HubSpot was. And trust me, there were a bunch of other factors in here. I definitely- I- I won't say that, you know, our team were- were like the sole driving force behind that- that shift in our strategy and approach, but certainly the data that we were able to collect and, uh, experiments we were able to run and the insights we were able to surface and the research we were able to synthesize, uh, gave us conviction to double down on it for sure. And that was definitely maybe the beginning of that inflection point for the company. But there were certainly a lot of other things that led to us wanting to become more product led. Like again, think about it, right? Like I think any company is probably searching for ways to operate more efficiently and if your revenue is so tied to like go-to-market headcount, like it gets really hard to scale the bigger you get, right? And so I think there's an innate desire to want to be more non-linear i- in our growth, right? And I think us arriving at the right place at the right time created sort of alignment around what the path forward could look like. Like what, like if we want to live in that world, how might we get there? And I think that's where we really fit into the equation. It's like, oh, we invest in this team. If we invest in the type of work this team is doing, that's how we're going to build efficiencies over time. And it's also we like that because it's in line with what our customers are already expecting from us.

    17. LRLenny Rachitsky54:47

        And it sounds like you weren't like, "We need to be more product led." It was more just, "How do we get the sales..."... process more efficient and the, the motion of growth more efficient, and that emerged out of that.

    18. CMChristopher Miller54:58

        Yeah. I mean, d- don't get me wrong, we were

15. 55:00 – 1:00:48

    Fallacies of product-led companies and how HubSpot embraced PLG

    1. CMChristopher Miller55:00

       definitely like, "We need to be more product led." (laughs) It's just like... Like, and, and, and I think that's actually the nuance here, right? Like you asked, you know, would I consider what we were doing product-led growth? And I, I think the answer is absolutely, but that's because a fallacy that people, a, a lot of, I think, maybe early stage founders or folks who are unfamiliar with product growth or maybe only know about it from, like, an academic point of view, uh, ma- maybe fall into the trap of, is assuming that, like, in order to be a PLG company that, that's, that's... You can use that interchangeably with, like, being a fully self-service business or a fully self-service go-to-market. I don't actually think that those things are one and the same. I think that most companies, at least the larger, more successful ones that have, sort of, done amazing things and are cornering their market or category that we would consider to be PLG companies have a, have a bunch of humans working on really important things, uh, when they go to market. And it's more of a hybrid motion and I think it's less about, again, being, sort of, like, myopic about your approach to PLG and, sort of, having it being really rooted in, like, principles that are, I think very, kind of, like, academic or conceptual in nature, but more, sort of, being pragmatic and saying, "Okay, cool. Like, who is our customer? What is the product that we sell? How are our customers used to buying this thing? How would they prefer to buy it in the future that they would like to live in? What's the packaging of our products? How do our customers decide? Is it a top-down decision or a bottoms-up decision? How complex are our billing and subscription terms? Is this something that's gonna be pretty transactional or something that's gonna be fairly considered? How comfortable is our target market with the technology in our category? Are they, are we competing against non-consumption or are we competing against competitors in the same category?" And if you actually answer those questions, uh, and I, I think it may be obvious where I'm going with this, but based on the answer to those questions, the conditions on the ground might lend themself to be more favorable to product-led growth and being more favorable to self-service, right? It's why there are companies that the value prop is just so... Like, you don't need a person to sell you Loom. Like I just, I use Loom and it's so intuitive that I can just decide on my own whether I wanna buy it. You don't need a person to teach you how to use even Slack, as an example. Like, Slack is extremely intuitive, right? Like, you would throw someone in Slack and they've used a product in a similar paradigm and they can probably figure out the basics on their own. There are certain products that don't necessarily check those boxes. And so I think what you can do is kind of take a more modular approach to PLG and it's, like, based on how a customer, in the best case scenario, might go from zero to one when he comes to, like, activation and onboarding. Do we need to have a human involved in that process at all or as a backstop? If the answer is yes, then, like, maybe figure out ways to have humans involved where your cost structure is, like, durable or, like, at least defensible. If that's not the case, then, like, go f- go take a PLG approach to it. And so, like, you know, across our entire business we don't, we've never taken, sort of, like, a very pure, "Everything here is, is, for this line of business or this product line is gonna be self-service," without, sort of, being able to defend and contextualize why across the entire customer journey this makes sense. And so yeah, we have customers who come in through the, the product-led front door and kick the tires on the product on their own and activate on the product on their own. But then when it comes time to buy the product, they wanna talk to somebody and there's legitimate reasons why, right? Like, there are maybe IT and security concerns that they need to get somebody on the phone for. Maybe they're coming for a platform where data migration is a huge fear they have, and that's not something that's easy to do in a self-service environment yet. I think that's gonna change over time. But today, it's still kind of painful when you're doing rip and replaces. And so to try to, like, brute force that into a, sort of, self-service motion for every customer at large would be solving for your business's desires and not necessarily solving for the customer at the end of the day. But we also sell into different segments of customers that are maybe digital natives but not familiar with products in our category. Uh, and maybe they're coming from, not a competing product, but they're coming from a more rudimentary system like spreadsheets. I mean, we've... I've, I've, I've seen customers using Post-it notes to manage their, you know, their, their, uh-

    2. LRLenny Rachitsky59:24

       Their CRM.

    3. CMChristopher Miller59:25

       ... their deal pipeline the real old school way, and that, like, that was sort of their locus of control for their sales team, right? And so there are use cases like that if you're a smaller team, you kinda have an acute understanding of the pain points that are, like, today's buyers that you need to put out. You don't have to deal with the burden of a huge data migration. And the person who's gonna be in the CRM day in and day out is also the person who gets to make the final call on what CRM they're gonna use. There's a ton of those customers that we never talk to in person, right? And, like, that's awesome too. And, and so being comfortable with things not necessarily fitting into, like, clean boxes and saying and, and, and, and having conviction that a modular approach or a more hybrid approach is actually the way to optimize for the customer and the business at the end of the day is, is something that I think we embraced really early on. Like, one of the first metrics that I had was activation rate, but it was also, how much demand am I sending to the sales team? And there was cer- no, like, turf war about that, right? It's like, oh, that's net positive for pe- if people are able to get helped and a lot of the questions that they have cannot be answered with the product today, we should absolutely be proud to connect them with one of our awesome people in sales who can, like, help see if the solutions we offer are a good fit for them. And there are instances where people just don't wanna talk to somebody and our job is to make sure that there's a friction-free way for them to make that decision on their own.

16. 1:00:48 – 1:04:35

    Advice for companies wanting to become more product-led

    1. CMChristopher Miller1:00:48

    2. LRLenny Rachitsky1:00:48

       Amazing. I think on the one hand this could be a whole podcast, is just talking about this, your PLG learnings.

    3. CMChristopher Miller1:00:54

       (laughs)

    4. LRLenny Rachitsky1:00:54

       Knowing it feels like HubSpot is one of the biggest success stories of transitioning more and more into PLG, at least at that point. Even though you're saying it was PLG early on, it feels like a huge shift to the business. So I really like this framework you just shared of...If you're trying to become more product-led, just think about the zero to one from visit to activation and when does someone really have to talk to someone and how do we help them not have to talk to people in that moment. So either in that direction or just broadly, if someone was trying to explore how do we become more product-led, what are kind of like the first couple steps and dives you would recommend they do to help them down that road?

    5. CMChristopher Miller1:01:34

       First I would ask, like, why do you want to be product-led?

    6. LRLenny Rachitsky1:01:37

       Mm-hmm.

    7. CMChristopher Miller1:01:38

       What assumptions are you making in terms of why being product-led are gonna be net positive for either the business or for your customers? And I might even ask them to define what product-led means to them-

    8. LRLenny Rachitsky1:01:49

       (laughs)

    9. CMChristopher Miller1:01:49

       ... so we can kind of get on the same page of what we're even talking about.

    10. LRLenny Rachitsky1:01:52

        How would you define it? Do you have like a rough... Do you have an answer to that just so people get a sense of what it probably means?

    11. CMChristopher Miller1:01:58

        Yeah, at the highest level it's like taking a go-to-market approach where your product's job is to grow revenue and you use humans as a backstop and not the other way around, right?

    12. LRLenny Rachitsky1:02:07

        Mm-hmm. Awesome.

    13. CMChristopher Miller1:02:09

        And, and I think the key thing is that, like, humans can be a backstop. There are moments where it's going to make sense for humans to be a backstop, right? One example that, like, is, I think is really normal, like, a hardship circumstance where a customer needs to, like, end their relationship, right? Like every C- every SaaS company deals with this. Some take a fully automated approach, but most usually have some sort of escalation path that will result in a human having to, like, resolve this. Like, it doesn't make them any less product-led. I think every company at its core is like having some humans behind the scenes interface with customers on things related to go-to-market, right? But I think once, like, defining that and getting on the same page about that, I think you can learn a lot. And, and by the way, like these are the normal conversations that I, that I have with, with founders all the time. I'm actually an operator in residence, uh, at OpenView, and so I speak to a lot of their portcos, and this is usually the conversation that we end up having. And I think what's always interesting is, like, how different the sort of array of answers are when you ask that question. Some are like, "Oh, it's about top of the funnel demand," right? Like, "We wanna be more product-led because we want more leads, we want more signups." You're like, "Oh, okay." I mean, and that, and that's like a very defensible reason, right? Like, there's a lot of data that shows that freemium products attract a lot more top of the funnel demand than, uh, you know, sales-led go-to-market products do, right? Some, it might be, uh, a matter of, like, constrained resources. Like, "We need to b- We absolutely need to be more product-led in this stage of the company because we simply cannot hire an army of, like, implementation specialists and folks on the customer success h- side of the house to, like, help every single customer at scale, uh, which is generally a byproduct of having a really large top of the funnel," (laughs) right? Um, and then there are others that are it's, it's about revenue efficiency, right? And so when you can kind of articulate the outcomes that you want to drive, it, it helps triangulate where to begin, right? So if you are really focused on top of the funnel demand, trying to do self-service checkout is a silly place to start, right? And so just like really doing the thought exercise of articulating like, why do you care about this? Like, why are you actually interested in this in the first place? If, if you do this, what would change about your business? Like, what assumptions are you making? And when you can actually list those things out, you can map them to parts of the customer journey where there may be opportunity to be more product-led if the company isn't there yet.

    14. LRLenny Rachitsky1:04:34

        Awesome.

17. 1:04:35 – 1:07:53

    Common mistakes to avoid when trying to start a PLG motion

    1. LRLenny Rachitsky1:04:35

       Maybe a couple more questions along these lines, and then I just have a couple more (laughs) questions I definitely wanna ask. When someone is trying to go in the direction of product-led growth, AKA more self-service, and I guess maybe let me just ask, is that sort of how you think about equivalency of those two?

    2. CMChristopher Miller1:04:50

       Sure.

    3. LRLenny Rachitsky1:04:50

       Okay. What are maybe the most common mistakes they make that aren't as obvious, you know?

    4. CMChristopher Miller1:04:55

       I mean, the number one mistake is, like, hiring a head of growth, giving them no resources, and expecting them to pull a rabbit out of their hat.

    5. LRLenny Rachitsky1:05:02

       Mm-hmm. Mm-hmm.

    6. CMChristopher Miller1:05:03

       I feel like every, you know, every PLG veteran has some joke that they tell about, you know, the poor head of growth who has no tooling, no engineering cycles, uh, no designer, no access to data, and then are, you know, handed a really scary big number and told to, to go move it. I think that's a, that's a common mistake that has stood the test of time. (laughs) Another one is expecting really a quick turnaround and thinking of it the same way you might think about hiring a sales, like an incremental sales headcount, which is that you're expecting near-term liquidity from that investment. But when you're doing PLG, it, at, at its core, it's still R&D, right? Like, you're still sort of planting seeds with the hope that, like, over time this is gonna play out in the form of, like, durable, high efficient growth. But if you're expecting, you know, you put a team on something and then you want those, that, that team to sort of have outsized impact, and sure there's gonna be low-hanging fruit, but I, I think just, like, not having the patience to see the investment through and, and cutting bait too early is another, uh, I think mistake some companies make. And then I also think that bad data hygiene is the other one, so not having taken a beat to properly instrument their product, messy data, no real self-service way for people to access that data. Like, having analyst bottlenecks can be a terrible position to be in. And so, uh, eating your veggies and, like, getting your house in order from a data standpoint I think is a crucial first step, because if you can't actually measure what's, what's happening, then, like, why? And then maybe the last one is people giving up because they don't have enough data, right? They're like, "We can't do PLG because we don't have this massive dataset the way that HubSpot has or the way that Airb- Airbnb has." And it's like, you can still do PLG, you just need to use different data. Like, the way we think about data is that, like, quant data is just another form of data, the same way experiment results are just another data point.... you can learn a ton from just talking to customers. Like qual research is super-duper important, right? And so if you don't have data to tell you exactly what every single person is doing in your product in aggregate, you can still talk to 10 customers and probably get a clear sense of what's happening and why it's happening, which you wouldn't even get from the quant data. So people sort of like getting demotivated, or companies getting demotivated because they're s- they think they're too early to do PLG. It's like, you can still do PLG. PLG at its core is just having your product sell the value prop of your... of what your business does, right? And you can s- you can still deliver on that without being able to stand up a very, like, robust and sophisticated experimentation practice.

18. 1:07:53 – 1:10:50

    How HubSpot structures growth loops

    1. CMChristopher Miller1:07:53

    2. LRLenny Rachitsky1:07:53

       Kind of along those lines, but going even broader. Without disclosing trade secrets about how HubSpot works, how would you describe the loop of growth of HubSpot? In the words of, you mentioned Brian Balfour and Farid, what is kind of the growth loop of HubSpot, either now or r- recently? Just like a simple way to think about how HubSpot grows.

    3. CMChristopher Miller1:08:12

       Our loops are less tactical. And in fact, like, if I'm being brutally honest, right, like I think loops are-

    4. LRLenny Rachitsky1:08:16

       Yes.

    5. CMChristopher Miller1:08:16

       ... kind of hard to achieve in B2B SaaS, right? Like I think there are some examples of that, but I think, like, some of the best loops come from, like, UGC, user-generated content. I think, like, a lot of B2C and, like, community-focused platforms can do loops really well. I think if it's like B2B SaaS, it's, like, hard to find things that get loopy. And, you know, that, that i- this is me going... (laughs) I think all my Reforge homies are gonna be upset that I said that, but, like, I think that's the truth. When I, when I think about the flywheel of HubSpot, I, I think it's a much... Like it's more of a macro flywheel, right? And, like, just to kind of lean into our own lingo, it's, it's really a attract, engage, and delight. And so one of the principles that guides our thinking and our strategy is, like, give value before you extract value. And I think that was at the core of inbound marketing at its inception, and that like outbound marketing was asking for something from customers or prospects before giving anything. And so at its core, it's like, okay, yeah, if you give a little for free, people who are interested in sort of hearing the rest of how that album sounds are gonna come and stick around for more. And so, in our pre-PLG days, it was content marketing, and, you know, white papers and listicles and e-books and things that people had to download that, uh, were really filling the top of the funnel. And that is t- just taking over the form with PLG, and so, you know, we, we intentionally put out a lot of free software. And the idea is that this software is not sort of gimmicky. It's not designed to run out of value on day one. It's actually designed so that our smallest customers can get some value out of it in a sustainable way. But if they're, if they're engaging with it deeply enough, they're gonna run into the limits of what that w- what that value is. And if we've done our jobs and delivered what we b- what we believe we, we were supposed to deliver, then the decision to purchase becomes a no-brainer. And if they're delighted with, you know, what it... The experience of being a customer, they're gonna become advocates, and they're gonna become promoters, and they're gonna tell their peers, because what we also know is that a lot of small business owners and even medium-sized business owners, uh, take a lot of guidance from their, their community of peers, right? And sometimes that's a digital community, sometimes that's not. And so anytime we win an advocate through delivering, like, an excellent customer experience, they bring more people into the top of the funnel. And so it's a really, like, honest, and I, I would say an honest macro loop in, in, in a sense, but like that's the way we, we think about our flywheel.

19. 1:10:50 – 1:16:11

    The importance of aggressive experimentation within new channels

    1. CMChristopher Miller1:10:50

    2. LRLenny Rachitsky1:10:50

       Oh man, this could be a whole other hour of a podcast just diving into this stuff.

    3. CMChristopher Miller1:10:53

       (laughs)

    4. LRLenny Rachitsky1:10:53

       This is so good I- I... Uh, you shared this interesting story that I didn't... I wasn't aware of. So HubSpot's kind of known for content and SEO. You know, you search for anything, there's always a HubSpot article about it. And so is what you're sharing here essentially that was like a big part of the early days, SEO free content that drove people to the site and the product wasn't free is, is what I'm hearing?

    5. CMChristopher Miller1:11:15

       Mm-hmm.

    6. LRLenny Rachitsky1:11:16

       And, and then it shifted to now it's a free product that anyone can use and that's what drives the top of funnel?

    7. CMChristopher Miller1:11:21

       Yes, correct.

    8. LRLenny Rachitsky1:11:22

       Amazing.

    9. CMChristopher Miller1:11:23

       I, I can't give a specific number, but, you know, a, a large percentage of our revenue flows through the product and it's not necessarily, like, maybe where people ultimately purchased, but that's their sort of first conversion event with us, right? Like, they were in the product, they liked what they saw, they spoke to somebody and then eventually became a customer and that, that is, like, now a pretty robust, uh, top of the funnel for, for the company.

    10. LRLenny Rachitsky1:11:45

        So I think this is a really interesting story of just starting with one growth channel of SEO essentially, content marketing, and then shifting to something else. Is there any lessons from that experience for people trying to s- kickstart their growth of SEO versus this freemium approach? Is there anything there that just, like, "This worked really well for us and you should probably try this," or SEO kind of runs out in this specific type of business?

    11. CMChristopher Miller1:12:10

        I'll, I'll admit I'm definitely not an SEO expert. I've been fortunate to work with some of the best marketers in the world who, you know, I, I think are bonafide legends at this point in terms of what they've been able to achieve at HubSpot and, and building that lead and sign-up machine. What I will say is being really aggressive about experimenting with new channels is so- Mm-hmm. ... important and diversifying your channel mix is so impor- it's, it's so important because things can change overnight and that might disrupt your entire funnel, right? Like, a Google algorithm change-

    12. LRLenny Rachitsky1:12:45

        Mm-hmm.

    13. CMChristopher Miller1:12:45

        ... uh, can have a massive impact. If you're reliant on app store optimization. A change in Apple's algorithm might have a massive impact. I mean, what we're seeing with generative AI, I think there's a lot of people losing sleep at night because it's unclear how this is gonna impact, like, SEO writ large, right? Like, if that's what fuels your entire business (laughs) is like being on Google's search result page, then like, what, what, what's gonna happen in this new sort of world we're about to enter? And so I think to the extent that you can...... not have your funnel be reliant on a single or a couple of channels is, is really important. We're always testing new channels. Like one of the channels that, you know, we're spending some time experimenting with is this concept of micro apps. And it's actually not a new concept for HubSpot. One of the first micro apps you ever built was a, was a, maybe Dharmesh built this, the original one, but it was called Website Grader, right? And it was a, you put in your domain and it crawled your site and then gave you a set of sort of recommendations for how you would optimize your site and it was free, right? It was definitely a one-trick pony, but what it did was it created an interesting conversation which is like, "Okay, cool, now that you have this information, what are you gonna do about it," right? And one of the things you could do is you could become a HubSpot customer, (laughs) and you can use our product to fix a lot of this stuff, right? And that worked for us. It worked really, really well. And so we've, we've done that play a few times and it's something that we'll probably continue to do. Like we have a bunch of these micro apps. We have like a brand kit generator. We have an email signature generator. We've experimented with like a build my persona generator. There's a couple of ones that I can't talk about right now but we'll learn a little bit about in a few weeks at Inbound, but, um, yeah.

    14. LRLenny Rachitsky1:14:28

        Hmm.

    15. CMChristopher Miller1:14:29

        Micro apps are an exciting new channel for us and, you know, some will be successes, some will flop and we'll probably sunset them, but, you know, being, being willing to fail in the pursuit of finding, you know, new distribution channels is also really important.

    16. LRLenny Rachitsky1:14:44

        That's an awesome insight. Is there a place people can go to find these micro apps that you all have built?

    17. CMChristopher Miller1:14:48

        Uh, there will be soon.

    18. LRLenny Rachitsky1:14:50

        Oh, mysterious. I also noticed Dharmesh tweeting about some AI projects he's working on. Is that related to these micro apps or is that just him on his own time just d- doing fun stuff?

Episode duration: 1:31:23