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

Chris Miller: … The actual 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 self-service, so we approached the team who owned it and we were like, “Are you all working on this?” They were like, “Nah, we’re working on a bunch of other stuff.” We were like, “Can we take this?” They were like, “Sure, if you want it.” And so, we took it and immediately blew it up, and so that attitude of saying that every problem is our problem and radical accountability and 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. When you do that, we look hungry, so let’s keep feeding us, right?

Conversation with Chris Miller

Lenny: Welcome to Lenny’s Podcast, where I interview world-class product leaders and growth experts to learn from their hard win 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 ICPM 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-like 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.

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The Intersection of Growth and AI

Chris Miller: I’m so excited to be on the podcast. Thank you, Lenny, for having me. This will be a lot of fun.

Lenny: 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?

Joining HubSpot and Early Experiences

Chris Miller: I’ve been leading PLG at HubSpot for several years now, and I recently took on the AI leadership role. It’s a special place to be in and 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’ve been in years past. So, it’s a really cool intersection point between those two things. There’s a lot we can do there.

Core Traits of Product Managers

Lenny: 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 and I’m going to 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 initiative in this time of AI?

Resilience and Coachability

Chris Miller: So when I joined HubSpot in 2016, it was definitely an element of timing that really worked in my favor. It was maybe like a year or so after HubSpot had launched their free CRM, which was a big strategic play for them and for us, excuse me, 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 going to happen after that. How are we actually going to get leverage and enterprise value out of this sort of big, enormous piece of free software we just put into the universe? And I think the pedigree of product manager at HubSpot at that time was also a bit different. There were folks who maybe started their time at HubSpot in support, and so intimately familiar with the product and with customers. Some of these people had closed thousands 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 I guess I understood 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. And so I think to answer your question, I think I was just willing to take some risks and really push for the things that I believed made sense even though maybe based on the titles that I had at the time, I wasn’t sort of inherently given a seat at the table and really pushed my away into some of these conversations and then was eventually invited to them. And so, just always had an interest in driving a strategy that was a click or two higher than maybe what my immediate team was focused on and was always curious about how other parts of the business functioned.

I used to spend a lot of time sitting on the sales floor, just going into the other buildings and talking to other folks, working on different parts of the business, and that’s part of maybe the serendipity that I miss about being in person, which is that you might just discover something from having a casual conversation with someone at the water cooler. You’re like, “Oh, that’s an interesting problem. I think my team can help with that,” so you absorb a bunch of context around 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. And so, if I had to guess how people might talk about that, if I wasn’t in the room, maybe they would cite that, but it’s tough to say.

Falling into Product Management

Lenny: Hard to do those serendipitous watercolor chats in these remote hybrid times, huh?

Chris Miller: Yeah, everything’s so scheduled and tightly scheduled and you’re bouncing from Zoom to Zoom and obviously HubSpot has embraced hybrid and there’s a ton of benefit to it. In fact, I was a new dad when I came back to work and my son wasn’t in daycare, and so it was so cool to just be able to pop out 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 you got to be a little bit more creative in terms of that serendipitous knowledge sharing, the osmosis learning, and just context sharing that happens more organically when everybody’s sharing the same physical space.

Serving Donuts and Scraped Knees

Lenny: 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 kind of in being a PM at HubSpot and/ or something that worked out really well, surprisingly?

First PM Role: B2B2C Challenges

Chris Miller: This is a funny story. For anybody at HubSpot listening, I apologize in retrospect for this, but-

Lenny: I’m excited for this.

Meeting Fareed Mosavat at Fitness Tech

Chris Miller: There was a time where we were having a lot of debates around pricing and packaging, and we’ll get into this, but our go-to-market model and sort of where we play in the addressable market created some complexity in the sense of we’re serving different parts of the market simultaneously with the 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 have a point of view on pricing and packaging? But the person I was working with, my designer, her name’s Mariah Moscato, she’s in product now, she’s excellent, we were part of a triad and we both had a similar school of thought in terms of what the pricing packaging could be.

And we were over in Dublin where we have our European headquarters and there was a party happening at the Guinness 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 and it was sort of one of those funny you should ask moments. And so, we ended up kind of pitching in the midst of pints being sort of handed every which way you could turn this vision for a completely different way we might approach pricing and packaging, and he was pretty intrigued and he said, “Why don’t you come to the next executive meeting and pitch us on it?”

I think that meeting was maybe a couple of weeks away and so we looked at each other and we were like, “Uh-oh,” not exactly what we expected in terms of, I think people welcoming maybe a contrarian point of view 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 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 their way over time into HubSpot’s pricing and packaging, but it certainly I think opened the door for us and for me, speaking for myself, certainly for me to be welcomed back into that room in the future and to be able to contribute ideas towards important decisions.

Lenny: I love that. It’s another example of serendipity and just running into people. Also, I think it’s a really good example of just how important it’s for PMs to be proactive and think ahead and not just rely on people coming to you, asking you for your advice and getting invited to rooms. I feel like so much of success in the product leadership role is just suggesting great ideas, being ahead of where people are and having the answers. You have the answer right there in the moment because you did the work ahead of time. Is that something you find as well that ends up being really important?

The Power of Data-Driven Decisions

Chris Miller: Yeah, one of the traits that I look for in PMs 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 traits is relentless curiosity, this 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 or you’re a part of or whatever mission you’re working on or whatever team you may be a member of.

Why You Must Talk to Customers

Lenny: Are there any other traits on that list of traits you look for that you think are really important that maybe other people don’t focus on?

Chris Miller: Yeah, relentless curiosity is probably my number one. My number two would probably be resilience, specifically if you’re working in growth. I think if you’re doing growth, right, if you’re doing product-led growth the right way, then you’re trying to balance the science and sort of taking a somewhat hygienic approach to validating assumptions and hypotheses with being really ambitious and really pushing for the things that are going to have massive impact for your customers at the end of the day. And when you’re doing that, you’re going to fail more than you’re going to be successful along the way. And if you’re not resilient, that can be really demotivating. I think there’s a stat that some growth person put out there years ago, which is that on average only 20 to 30% of experiments of growth team runs might be successful. So, that means 70 to 80% of the time 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. 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, you’re thinking too small. And so, that resiliency piece is certainly important in my mind. I think coachability is another one in the sense that I still think that the sort of subcategory of growth product management is still fledgling compared to PMs working on 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 mostly an unreasonable ask, but it can certainly be taught and even if you do have some experience doing PLG work, it’s important to know that what that work is going to look like is going to 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 PMs, and then creativity is so important too. Valuing simple solutions to really hard problems, I think if building the next super sophisticated widget is the thing that gets you out of bed in the morning, growth might not be for you, I think the best growth product leaders and growth minds that I’ve worked with over the years or have had the privilege of learning from over the years, I think the thing that I noticed about them is they’re almost ambivalent to the solution and certainly ambivalent to how complex a solution may or may not be. And taking 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 really cool trait, and I kind categorize that under creativity.

Surprising User Research Discoveries

Lenny: 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 founder was just like, “I’ve read that the cure to all our problems is going to be hiring product manager,” and you heard that and you googled, what is product management, and then you asked them, “Can I do that?” And that’s how you got into the role. So first of all, is that true? And second of all, what’s your advice to people trying to get into product management and any lessons from that experience?

Chris Miller: So first, yes, that is 100% true. That is how I stumbled into product management. So, I appreciate all the folks who took a shot on me back then, but this was at a time where I would say product management even as a function was definitely not ubiquitous across tech. There was, at least in the world that I was in, a lot more of a standard waterfall approach to building product with a lot of middle layers and engineering managers and really no one who had the job of owning the problem from a customer’s point of view. And so, there wasn’t a ton of content out there. There weren’t even a ton of people in the city at the time that I could really talk to sort of learn, and so a lot of what I did was scrape my knees through the first years and a lot of painful trial and error.

And then eventually I think there’s a lot more energy and an interest around the trade craft and the function, and so I think it’s much easier today for someone to learn the fundamentals of product management without necessarily needing to do it via trial by fire. My advice to folks who are interested in breaking into product management specifically is focus on a few things. One, focus on structure. I think there’s usually a lower barrier to entry to do product management at a smaller shop, which they might not have as much access to the best talent out there, but I think what you may often give up in those instances is structure to your own sort of professional development and formal training and education and potentially even the opportunity to work for people who are truly battle tested and have seen the movie several times and can actually wisdom share because truthfully, it looks different in every company, and so it is one of those functions.

I do believe that taking a truly academic approach towards upskilling has fairly diminishing returns because it’s tough to field curveballs in a classroom. And so, choosing where you want to break in is almost as important as choosing that you want to break in the first place. 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 where you are working at a different function and you’re sort of product curious, go talk to the PMs, literally I say go reach out to a PM and ask how you can make their day easier.

Figure out what you can do in your spare time that they can offload to you and do a little bit of volunteer labor, even if that’s just shadowing because I think just getting that context and understanding the sort of rhythm of how a team ideates and defines problems and prioritizes and ship 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, just getting that hands-on experience or at least direct sight-line into the day-to-day of a team 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 at the very least, what you get out of it is hopefully an advocate or a sponsor at the end of the day who is willing to gamble some professional and political capital on you to get your foot into the door even though you might not have any formal experience on your resume.

HubSpot’s Secret to Success

Lenny: There’s so much stuff that super resonates there. One is that I always think of the bare minimum job of a PM is just to be useful to people on the team and help them do better work. If you do that alone, people-

Short-Term Survival vs. Long-Term Vision

Chris Miller: Bring the donuts, right?

Systematizing a Customer-First Approach

Lenny: Bring the donuts, exactly.

Chris Miller: I must be old, I don’t know that anybody uses bringing the donuts now anymore.

What Makes HubSpot Special: SMB Focus

Lenny: No, we had Ken on the podcast, we talked about it. We asked, what is the digital version of that when everyone’s 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 read these things, take some courses and you got this, and you’re not going to mess up, but I find that messing up is so important in helping to learn to do the job because like you said, there’s relationships and people and changing plans and leaders, and it’s just like you’re not going to 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 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. 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?”

Chris Miller: So, my first product management job/mission was working on a B2B2C product, and there’s a lot of unique challenges that came with that. 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 own the relationship with the end user and not us, and so-

… own 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 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 going to delight the person using it at the end of the day, or provide magical value. And so, I think I probably shipped a lot of bad product those years, if I’m being completely honest. I don’t know that I would look back at what I shipped back then or what we shipped back then, and say 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.”

The HubSpot Culture Code

Lenny: Where was that? Was that with Keeper?

Chris Miller: I was 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 know you know, Fareed Mosavat, who I believe was on the pod-

Fun HubSpot Culture Stories

Lenny: Ooh. Absolutely.

Early Playbook for HubSpot’s Growth Team

Chris Miller: … last October. Shout out to Fareed if you’re listening. Fareed is a good friend and mentor, and he 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-tracking app. And so, we spent a lot of time talking to users directly, and a lot of guerrilla user research techniques. Literally, sometimes going outside and just talking to runners in passing to understand what were the challenges in finding motivation, and why do they choose running assistance, running applications in the first place? And so, just that having that deep connection to the customer and not feeling like you’re being kept at arms’ distance was eyeopening. 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 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, we can prove causation from a business impact standpoint or a customer delight or 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 they land on Oz, and all of a sudden, everything’s in Technicolor. And you’re like, “Oh, my gosh, I can actually make informed decisions about what I’m shipping.”

And having 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, I would say, behaviors and just philosophy around product discipline that I learned from Fareed and that group of folks that I worked with closely during those years. And that was, I think the… I consider that to be when I really became a product manager.

Lenny: There’s two things I want to highlight there that, again, super resonate. One is just whenever I talk to customers, I’m like, “Why don’t I do this more often?” Because every time it’s like, “Wow, I had no idea how big of a problem that was. 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 if you’re listening and you’re just like… Maybe just go talk to a customer today.

Crazy Sprints and Breakthrough Moments

Chris Miller: Talk to customers, and we also learned a lot from talking to people who we wanted to be customers but were not, right? And people who had either broken up with our product or evaluated it and never fell in love with it in the first place. And so, I think every PM struggles with 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 finding time to just talk to people. Even today, 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 maybe assume that some of these decisions are? And then you often learn that they’re sometimes kind of emotional, really instinctual and visceral and maybe connected to brands more than they even connected to product. And there’s a lot of things that I think when you’re in the proverbial digital conference room with your team, trying to understand what makes your users tick, you’re just like, “We’re actually just…” We’re illogical humans at the end of the day at our core, and 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 love it to be perfect science, so that we can moneyball the system, if you will.

HubSpot’s Shift to Product-Led Growth

Lenny: It reminds me of a story where we were doing some user research on a booking feature with an Airbnb. And we went to Paris to do these really in-depth user research studies. We were 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 it 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 look at all this power you get.” They’re like, “No, I don’t care. I don’t trust it.” And-

Hybrid Strategies in Product-Led Growth

Chris Miller: Yeah, that’s why talking to customers is so… You could have all the usage data in the world, that’s going to tell you what’s actually happening in your product, but it doesn’t tell you why. It will never explain the why behind a behavior that you can track through events firing. And so, that’s why that sort of proximity to the customer and directing that sort of relentless curiosity towards the qualitative stuff is so, so important because you just learn things that are just sometimes really unintuitive or are blind spots because we’re often not the people we’re building product for.

Defining Product-Led Growth

Lenny: 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 manager, Fareed in this case, who helped you learn the craft and develop your skills, and that’s the exact experience I had too. Just 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 care stagnating? See if you can just find… Easier said than done, but oftentimes it just takes one person to change everything.

Misconceptions About Becoming Product-Led

Chris Miller: It gets into sort of a conversation about the difference between a manager and a mentor, 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 for me, calling them mentors, I think sells what they were very short. And I would actually describe those folks as being sponsors and advocates, people who were willing to put up capital, whether that’s professional, social capital to bet on you.

I mean, truth be told, when I interviewed with Fareed that first time, I think back to the interview and I think I bombed it. I actually don’t think I would’ve hired me back then. And I remember the answers I gave to some of those questions, and I think they were good, but I don’t think they were certainly great. And I imagine that there was something in there where the decision maker, who was Fareed said, “I think I can make something out of this.” 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, 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.

Lenny: Is there anything that you think you did right to help find mentors and sponsors and advocates for people that are thinking about, “Hey, 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?

Common PLG Misconceptions

Chris Miller: Something I think I certainly continue to work on, but really, putting ego aside and embracing not knowing stuff 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 at least be great at something overpower the fear of being inadequate at something. And I played sports growing up, and so I like being coached. I can take hard feedback, and I like it because if I get better feedback than the people I’m competing against, I think I can beat them over time if I work hard enough.

And so, I think just 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 me at all, but who might get delight out of it somehow. And I don’t know exactly how that works and the calculus that goes on in folks’ brains, but at least what’s within my control is how I can show up in the context of those relationships and really embrace even the hardest, ugliest feedback and hope that I can extract something from it that’ll make me better at the end of the day.

The HubSpot Growth Flywheel

Lenny: 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 completely disagree with what they’re telling you.

Chris Miller: Yeah, shout out to Jules. Jules is also someone who has been generous with me in the past in terms of giving time when I’ve needed help with stuff. Also, a great episode you did with Jules.

The Importance of Channel Diversification

Lenny: So, many people have said what you just said about Jules, about how helpful he is been to them. So, clearly, a class act to that guy, maybe we’ll have to bring him back.

Chris Miller: Would love that.

How Covid Accelerated Growth

Lenny: Yeah. V2 Jules. So, let’s shift to HubSpot the business, which is a pretty incredible success story. From what my notes, it’s worth something like $30 billion 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 showed 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 because 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?

Chris Miller: There’s a lot in there. I can speak to the things that have resonated most deeply with me in my time there. The first is legitimate customer obsession. It’s not marketing, it’s legitimate, right? 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 how we think about the business and why the company exists in the first place, really walking the walk there is something that I don’t know that that’s true everywhere.

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, the right thing for the customer? Being really challenging. I think just sort of having that 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-

Lightning Q&A Round

Lenny: Before you actually move on to the next one, I want to spend a little time on this one because I think people hear this and they’re like, “Yes, okay, we’re going to be customer obsessed.” And then, you have to make these hard decisions. Look at this experiment, it’s going to grow our revenue 1%, but it’s not really going to make the customer’s life easier. How do you actually make this real? And there may be an example where you have to trade off growth versus 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.

Chris Miller: One, I think that’s a really fantastic, 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? And typically, when you’re making decisions that could be described as hostile towards your customers, but a net positive for the business, you’re probably not thinking long-term enough, right? Because there’s no possible way, unless you have completely cornered a market and there is no competition whatsoever, that you could continually be hostile towards your customers and grow, right? At some point, that’s going to 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, where are we going? What’s the path that we’re actually charting? Is I think the true tension. But if you’re making decisions that might have lasting impact that are customer hostile, I think that’s a really dangerous path to kind of go down. And so, having, I think, the discipline or the bravery or the courage, whatever, to I think focus on not necessarily tomorrow or the day after, and really think about two, three, four years from now, what are the outcomes we’re trying to drive and what are the decisions we need to make in the interim that are going to lead to that outcome? If you stick to that sort of framework, or first principle is a better way to describe it, then 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.

Guiding Life Principles

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

Chris Miller: There’s definitely structure you could put around customer centricity. And I think a lot of it for growth at HubSpot and the teams that I lead, it’s around forcing specificity of language. So, for example, you look at a lot of standard documentation for features or experiments, whatever, and one of the first things, it’s like outline the problem. I don’t know that we even talk about problems without a qualifier. Are we talking about a business problem? Are we talking about a customer problem? Are we talking about an efficiency problem? Describe the nature of the problem and parse it out. Because generally speaking, if there’s a business problem, you might do the thought exercise of asking, “Well, why hasn’t that problem solved itself? What’s the actual customer problem that is leading to the downstream negative thing that’s happening to the business?”

And if we can actually 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, what would you predict to be some of the sort of derivative downstream things? And if we can call those things out and just keep asking why, why, why, to sort of justify some of the direction you want to go in and then keep asking in what, what, what, in terms of what’s the sort of true blast radius and domino effect of these decisions is the approach that we take at HubSpot, in my teams at least.

Recent Favorite Products

Lenny: Awesome. Okay. So, I cut you off in this one bullet point so far. So, let’s keep going.

Chris Miller: Yeah. So we’re talking about the things that make HubSpot special. So, customer obsession is definitely one. I think where we play in the market, too. Being a company that has been comfortable staying in the mid-market, SMB mid-market space, and resisting the temptation to try to crawl up into enterprise software, I think makes us special. And one of the things that’s actually really straightforward, which is that a lot of enterprise software companies, a lot of your revenue is tied up in a small subset of customers. And I think what can happen there is if those customers decide that they want you to build something and they’re willing to threaten their business over it, then you’ll end up building it. And is that necessarily the thing that is going to serve all your customers best? Probably not. Are you going to 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. 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 what that does is with great power comes great responsibility. I think what that does is the 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 the guiding light behind some of our decisions around connected experience and usability and user experience. And so, playing in the mid-market, I think affords us to be able to do that. So, I think that’s another thing that makes us special for a company of our size.

Culture is another one. And I won’t get into the culture code. I think a lot of folks have probably read it. If not, go check it out.

Lenny: I don’t know if people have heard of that. What is that?

Chris Miller: Yeah. Dharmesh, our co-founder, one of our fearless leaders, Dharmesh, 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 anywhere. I think a lot of companies sort of replicated that over the years, but by being really open and transparent about the culture both internally and externally, I think one, it internally creates alignment and it gives everyone something to point to to enforce why did we choose to work with each other the way that we work with each other. 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 I think a lot of quality people crave a lot of the things that are sort of codified in our culture. Humility, empathy, 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 being willing to sort of pressure test it on a regular basis, like is this still a company we want to be? We are growing really fast. What has changed? What conditions are still able to be supported with the culture we have codified today? What amendments might we need to make in terms of who we want to represent ourselves to be to our customers and how do we want to work with each other? And investing in that, hiring really good people that can help us scale that I think is something that makes HubSpot really special.

Lenny: Amazing. I’m reading the culture code on the side here, and there’s these little quotes that are really sweet. I really like this one, “Solve for the customer, not just their happiness, but also their success.”

Chris Miller: Yes.

Lenny: Wise.

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

Chris Miller: Yeah, there’s a ton, but I think there’s definitely a very legitimate school of thought around how culture can both contribute to inclusion, but also, be a headwind to inclusion. I think a lot of the things that I might associate with 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 working in the same physical space. And so, there’s a lot of inside jokes. And sometimes 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 two or three years and that flies over your head-

The company in the past two or three years, and that flies over your head. I think we have to ask ourselves, “What’s the value of continuing to embrace these things?” And so I think what we’ve been doing over the years is taking inventory of the things that might have been considered part of HubSpot legacy culture and really trying to again, pressure test it. Does this continue to serve us today? And if not, we should be really comfortable of letting it go.

But one of the things that I think is super dope that we do is we do this thing called PEER Week, which was something that popped up during the pandemic and the TLDR is that it’s like an event for product and engineering; where travel changed with the pandemic and people don’t get to see each other in person as much, but there’s a couple of weeks in the summer in June where we fly everybody in either if you’re in North America, we fly you to Cambridge. If you were in Europe somewhere, then we fly you to Dublin and we spend a week together.

There’s not a ton of focus on just classic productivity. There’s a ton of focus on building connections and safety and just getting to know people and who they are as human beings, but also, damn I forgot how much I missed whiteboarding. It’s actually being able to get in a room with a physical whiteboard of people and work on some stuff. And so this is, I think the second year in a row, or second or third I don’t remember, pandemic years have really fogged the brain… That we’ve done it. And it’s one of the things I look most forward to every year is getting everybody in the same city to just hang out.

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

Chris Miller: I would say the early years of doing freemium. And for the record, there’s definitely 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 PLG DNA into HubSpot. So shout out to Brian. I want to make sure he gets the credit that he’s owed.

Lenny: Yeah, we’re going to have him on the podcast at some point. It’s in the works.

Chris Miller: Yeah, he’s a legend. Brian’s great.

Lenny: Absolute legend.

Chris Miller: And so after Brian had left HubSpot, it was a bit start and stop. And so when I joined and we sort of took another stab at it, I think there were a few things we did. One, in the beginning is we really had an aggressive mentality, an aggressive approach I think. And by we, I mean the team, the actual 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 the sales tool, activation team. It was a very boutique mission and remit compared to I think a lot of the other teams at HubSpot’s missions and remit at the time.

But even though that’s what we were supposed to be working on paper, we were sort of like, if we find something that looks like an opportunity and no one else in the business is thinking about it, we’re just going to try to fix it. We’re going to ask for forgiveness rather than permission and start to call some plays.

And what that looked like was at the time, a very small percentage of, I think HubSpot’s subscription revenue would be described as self-service, like people putting in their credit card and buying something. It was predominantly product driven leads like PQLs. And so we were literally sending everything to the sales team, which it was running revenue, but certainly opportunities for efficiency because it was the first time we’d really had a product at a price point that could be transactional and not a highly considered purchase. And so we were thinking about this and we were like, “Well, how does this work? Is there even a pricing page in the product that people could 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 code to that repository.

So we approached a team who owned it and we were like, “Are y’all working on this? Is this an active development?” And they were like, “Nah, we’re working on a bunch of other stuff.” We were like, “Can we take this?” And they were like, “Sure, if you want it, take it. 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, how are people getting to 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, how do we actually just remove the friction that’s standing in the way?

And so we did a mad dash towards this outcome we wanted to drive, and when we released it worked. It was actually a step function change in the way that the physics of the business and the funnel really looked. And I think that was probably a catalyst moment of everyone saying, “Oh wow, there might actually be something here.” And so that attitude of saying that every problem is our problem and being willing to really take a mentality of like, I think radical accountability and 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, I think the business, a business may get more comfortable putting more on your plate. Right? And so it’s like we look hungry, so let’s keep feeding us. And so over time our remit expands and there’s other things that we think are opportunities to gain leverage for the business or deliver a delight to our customers in a more efficient way, and honestly in a way that they probably expected to engage with us at that point in time. It was quite odd that there were so many humans involved in every stage of the customer journey and some of our customers just like, “I just want to be able to try the thing and buy it if I want to be. I really don’t want to be forced into a sales engagement.” And so it was really kind of meeting the expectations of the modern software buyer in many ways.

Lenny: It sounds incredibly important. Basically your team turned HubSpot into a very product led growth business, which feels very important in the history of HubSpot’s growth. Would you consider what was there before where it was the beginnings of self-service, but they had to talk to a salesperson? Would you consider that product led?

Chris Miller: Yes.

Lenny: Okay.

Chris Miller: Yes.

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

Chris Miller: 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 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 won’t say that our team were the sole driving force behind that shift in our strategy and approach, but certainly the data that we were able to collect and the experiments we were able to run and the insights we were able to surface and the research we were able to synthesize… It 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 was certainly a lot of other things that led to us wanting to become more product led.

Again, I think about it, I think any company is probably searching for ways to operate more efficiently. And if your revenue is so tied to go-to-market headcount, it gets really hard to scale the bigger you get. And so I think there’s an innate desire to want to be more non-linear in our growth. 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. 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.

Lenny: 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 motion of growth more efficient and that emerged out of that.

Chris Miller: Yeah, I mean, don’t get me wrong. We were definitely like, we need to be more product led. And I think that’s actually the nuance here. You asked would I consider what we were doing product led growth? And I think the answer is absolutely, but that’s because a fallacy that people, a lot of, I think maybe early stage founders or folks who are unfamiliar with chronic growth or maybe only know about it from an academic point of view, maybe fall into the trap of is assuming that in order to be a PLG company you can use that interchangeably with being a fully self-service business or 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 done amazing things and are cornering their market or category, that we would consider to be PLG companies have a bunch of humans working on really important things on their go to market, and it’s more of a hybrid motion. And I think it’s less about, again, being sort of myopic about your approach to PLG and having it being really rooted in principles that are, I think very kind of academic or conceptual in nature.

But more sort of being pragmatic and saying, “Okay, cool. 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 building and subscription terms is something that’s going to be pretty transactional or something that’s going to be fairly considered? How comfortable is our target market with the technology in our category? Are we competing against non-consumption? Are we competing against competitors in the same category?”

And if you actually answer those questions, and 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 themselves to be more favorable to product-led growth and be 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. I use Loom and it’s so intuitive that I can just decide on my own whether I want to buy it. You don’t need a person to teach you how to use even Slack to some example. Like Slack is extremely intuitive. Right? Like you could throw someone in Slack and use a product in a similar paradigm and it 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 it comes to 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 maybe figure out ways to have humans involved where your cost structure is durable or at least defensible. If that’s not the case, then go take a PLG approach to it.

And so across our entire business, we’ve never taken a very pure, everything here for this line of business or this product line is going to be self-service without 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 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 want to talk to somebody and there’s legitimate reasons why, right? 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 going to change over time. But today it’s still kind of painful when you’re doing rip and replaces.

And so to try to brute force that into a sort of self-service motion for every customer writ large would be solving for your business’ desires, 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. And maybe they’re coming from not a competing product, but they’re coming from a more rudimentary system like spreadsheets. I mean, I’ve seen customers using post-it notes to manage their.

Lenny: [inaudible 00:59:25].

Chris Miller: The deal pipeline, the real old school way, and 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 kind of 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 going to 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 going to use. There’s a ton of those customers that we never talk to in person, right? And that’s awesome too. And so being comfortable with things not necessarily fitting into clean boxes 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 something that I think we embraced really early on.

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 no turf war about that, right? It’s like, oh, that’s net positive for 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 be like, help see if the solutions we offer are a good fit for them. And there are instances where people just don’t want to 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.

Lenny: Amazing. I think on the one hand, this could be a whole podcast is just talking about your PLG learnings, 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 the first couple steps and dives you would recommend they do to help them down that road?

Chris Miller: First I would ask, why do you want to be product led? What assumptions are you making in terms of why being product led are going to be net positive for the business or for your customers? And I might even ask them to define what product-led means to them that we can get on the same page of what we’re even talking about.

Lenny: How would you define it? Do you have a rough, an answer to that? Just so people get a sense of what it probably means.

Chris Miller: Yeah. At the highest level, it’s like taking a go-to-market approach where your product job is to grow revenue and you use humans as a backstop and not the other way around.

Lenny: Awesome.

Chris Miller: And I think the key thing is that humans can be a backstop. There are moments where it’s going to make sense for humans to be a backstop. One example that is I think is really normal, a hardship circumstance where a customer needs to end their relationship, right? Like 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 resolve this. It doesn’t make them any less product led. I think every company at its core is having some humans behind the scenes interface with customers on things related to go-to-market. But I think once defining that and getting on the same page about that, I think you can learn a lot. And by the way, these are the normal conversations that I have with founders all the time. I’m actually an operator in residence at OpenView, and so I speak to a lot of their poor [inaudible 01:03:01], and this is usually the conversation that we end up having.

And I think what’s always interesting is 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. We want to be more product led because we want more leads, we want more signups. You’re like, “Oh, okay.” And that’s a very defensible reason. There’s a lot of data that shows that freemium products attract a lot more top of the funnel demand than sales led go-to-market products do. Right? Some, it might be a matter of constrained resources. We absolutely need to be more product led in the stage of the company because we simply cannot hire an army of implementation specialists and folks on the customer success outside of the house to help every single customer at scale, which is generally a byproduct of having a really large top of the funnel. And then there are others that are, it’s about revenue efficiency.

And so when you can kind of articulate the outcomes that you want to drive, it helps triangulate where to begin. So if you are really focused on top of the funnel demand, trying to do self-service checkout is a silly place to start. And so just really doing the fun exercise of articulating why do you care about this? Why are you actually interested in this in the first place? If you do this, what would change about your business? 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.

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

Chris Miller: Sure.

Lenny: Okay. What are maybe the most common mistakes they make that aren’t as obvious?

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

I feel like every PLG veteran has some joke that they tell about the poor head of growth who has no tooling, no engineering cycles, no designer, no access to data, and then are handed a really scary big number and told to go move it. I think that’s a common mistake that has stood the test of time.

Another one is expecting really quick turnaround and thinking of it the same way you might think about hiring a sales, an incremental sales headcount, which is that you’re expecting near term liquidity from that investment, but when you’re doing PLG at its core, it’s still R&D. You’re still sort of planting seeds with the hope that over time this is going to play out in the form of durable pie efficient growth. But if you’re expecting, you put a team on something and then you want that team to sort of have outsize impact, and sure there’s going to be low hanging fruit, but I think just not having the patience to see the investment through and cutting bait too early is another, 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 eating your veggies, 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 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 data set the way that HubSpot has or the way the Airbnb has. And it’s like you can still do PLG, you just need to use different data. The way we think about data is that 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, 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. That you wouldn’t even get from the quant data.

So people getting demotivated or companies getting demotivated because they think they’re too early to do PLG, you can still do PLG. PLG at its core is just having your product sell the value prop of what your business does, and you can still deliver on that without being able to stand up a very robust and sophisticated experimentation practice.

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

Chris Miller: Our loops are less tactical. In fact, if I’m being brutally honest, I think loops are kind of hard to achieve in B2B SaaS. I think there’s some examples of that, but I think some of the best loops come from UGC, user generated content. I think a lot of B2C community focused platforms can do loops really well. I think if it’s B2B SaaS, it’s hard to find things that get loopy. And it is me going, I think all my Reforge [inaudible 01:08:40] are going to be upset that I said that. But I think that’s the truth.

When I think about the flywheel of HubSpot, I think it’s more of a macro flywheel. And just to kind of lean into our own lingo, it’s really attracting gage and delight. And so, one of the principles that guides our thinking and our strategy is give value before you extract value. And I think that was at the core…

Give value before you extract value, and I think that was at the core of inbound marketing at its inception, that 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 going to come and stick around for more. And so in our pre PLG days, it was content marketing and white papers and listicles and eBooks and things that people had to download that were really filling the top of the funnel. And that is just taking another form with PLG.

And so 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 engaging with it deeply enough, they’re going to run into the limits of what that value is. And if we’ve done our jobs and delivered what we believe we were supposed to deliver, then the decision to purchase becomes a no-brainer.

And if they’re delighted with the experience of being a customer, they’re going to become advocates, and they’re going to become promoters, and they’re going to tell their peers. Because what we also know is that a lot of small business owners and even medium-sized business owners take a lot of guidance from their community of peers. And sometimes that’s a digital community, sometimes that’s not. And so anytime we win an advocate through delivering an excellent customer experience, they bring more people into the top of the funnel. And so it’s a really honest, and I would say an honest macro loop in the sense, but that’s the way we think about our flywheel.

Lenny: Oh man, this could be a whole other hour of a podcast just diving into this stuff. This is so good. You shared this interesting story that I wasn’t aware of. So HubSpot’s kind of known for content and SEO. You search for anything and there’s always a HubSpot article about it. And so is what you’re sharing here, essentially that was a big part of the early days, SEO, free content that drove people to the site and the product wasn’t free, is what I’m hearing. And then it shifted to now it’s a free product that anyone can use and that’s what drives the top of funnel.

Chris Miller: Yes, correct.

Lenny: Amazing.

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

Lenny: 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 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?

Chris Miller: 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 I think are bonafide legends at this point in terms of what they’ve been able to achieve at HubSpot and building that lead and signup machine.

What I will say is being really aggressive about experimenting with new channels is so important, and diversifying your channel mix is so important because things can change overnight and that might disrupt your entire funnel. Like a Google algorithm change can have a massive impact. If you’re reliant on app store optimization, a change in Apple’s algorithm might have a massive impact. 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 going to impact SEO writ large. If that’s what fuels your entire business is being on Google search result page, then what’s going to 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 relying on a single or a couple of channels is really important. We’re always testing new channels. One of the channels that we’re spending some time experimenting with is this concept of microapps. And it’s actually not a new concept for HubSpot. One of the first microapps you ever built was a… Maybe Dharmesh built this, the original one, but it was called Website Grader. And it was you put in your domain, and it crawled your site, and then gave you a set of recommendations for how you would optimize your site. And it was free. 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 going to do about it? And one of the things you could do is you could become a HubSpot customer and you can use our product to fix a lot of this stuff.

And that worked for us. It worked really, really well. And so we’ve done that play a few times and it’s something that we’ll probably continue to do. We have a bunch of these microapps. We have a brand kit generator, we have an email signature generator. We’ve experimented with 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 yeah, microapps are an exciting new channel for us. And some will be successes, some will flop, and we’ll probably sunset them. But being willing to fail in the pursuit of finding new distribution channels is also really important.

Lenny: That’s an awesome insight. Is there a place people can go to find these microapps that you all have built?

Chris Miller: There will be soon.

Lenny: Oh, mysterious. I also noticed Dharmesh tweeting about some AI projects he’s working on. Is that related to these microapps? Or is that just him on his own time just doing fun stuff?

Chris Miller: Very related to microapps. I would say ChatSpot is actually, and for those who don’t know what ChatSpot is, ChatSpot is a bit of an AI copilot that Dharmesh built that has sort of been very positively received by both HubSpot customers and non-HubSpot customers alike. And so that’s something that we’re, wearing my AI hat, spending a lot of time thinking about, sort of what direction do we want to go in the ChatSpot.

But again, it was something that we put out in the universe to see what happens. And now it’s like, oh, we’re getting an interesting amount of signups every month. Who would’ve guessed that? I don’t think that… That definitely wasn’t on the roadmap a year ago. And I think being a 17-year-old SaaS company that can still operate with that sense of urgency and pace helps a lot to why wait to get consensus on a decision when we can put something out there and then see what happens and see what the data says.

Lenny: Yeah, I was just going to say that it feels like it’s such a win-win-win, including it’s just a release for people on the team that have been there for a long time just to work on something totally different and new and just launch a new product.

Chris Miller: Yeah, 100%.

Lenny: I love that. Is there anything that just significantly accelerated growth in the last, I don’t know, number of years that was like, wow, this really changed the game.

Chris Miller: Covid. Covid was obviously challenging and awful on so many levels, but it was scary. It was super scary. We were all terrified. We didn’t know what it meant for our jobs. My own sister, who also works at HubSpot now, she at the time was transitioning into hospitality and was two months into her job when she got furloughed because of Covid. So who knew what the world was going to look like and how it was going to impact businesses?

I think we were prepared for the worst, and we actually caught a bit of the Covid tailwind and a lot of other businesses did, because companies who never had to think about digital marketing all of a sudden had to, and it was urgent. It was a burning need for them to figure out how they were going to weather the storm. And I think one of the things that HubSpot did, and this is one of the sort of phrases we use internally, is never waste a good crisis.

And so, one of the things we leaned into was sort of goodwill pricing, and we lowered the price on some of our tools and created some temporary leniency around certain things. And just the removal of that friction ended up being a really interesting tailwind for the business and specifically for the business that I run, which is our starter business, our free and starter business, we really accelerated growth during that period, which was not… I think if you would’ve looked at my Bingo card in March of 2020, I don’t know that I had that on the Bingo card.

Lenny: I’m looking at the stock price in another window here and I could see what happened. That went great, and even it came down with the whole market, but it’s coming right back up. With that, we reached our very exciting lightning round. I’ve got six questions for you. Are you ready?

Chris Miller: Yeah.

Lenny: What are two or three books that you’ve recommended most to other people?

Chris Miller: Truthfully, I don’t read a ton of books. Got a one and a half year old. I also probably didn’t read a ton of books before, but it’s a nice excuse to have. That’s why I don’t have time to read today. But when I think of books that I think about a lot still, there’s a book called Everybody Lies, and it’s a book… I believe the guy who wrote it was a data scientist at Google. And part of the message is that everybody’s a data scientist and really trying to democratize the idea of using data in your everyday lives to make decisions and demystifying the idea of data science. But the way he kind of does this is through comparing Google search data and what we know people to be actively looking for answers for, with sort of qualitative survey data. And people lie on surveys all the time for a variety of different reasons, but no one lies to Google because it’s transactional. If I lie to Google, I’m not going to get what I want. And so it kind of really explores what it means to tell the truth and how honest we are with ourselves and with the internet. And so I really love that book.

The other book I really love is Chop Wood Carry Water, which it’s like a parable about a young boy who wants to become a samurai. But the sort of message of the book is about falling in love with the process, especially the most mundane parts of a process of becoming great at something. And that’s something I… It’s a good reminder about patience, humility, and sort of taking things one step at a time. And I often reference Chop Wood Carry Water a lot.

Lenny: Reminds me of The Score Takes Care of Itself, I think is the name of the book.

Chris Miller: Yeah, yeah, I’ve heard of it.

Lenny: Bill Walsh. Amazing. Okay. What’s a favorite recent movie or TV show?

Chris Miller: Oh, man. On Amazon Prime, I’m a Virgo, and it’s a Boots Riley show. Boots Riley directed Sorry to Bother You. It just blew my mind. It’s super surreal and funny and dark and it stars Jharrel Jerome, who I think he played one of the characters in the Netflix Central Park Five. I think he won a couple of awards for that too. And that was a show I watched recently where I had no expectations going into it other than I knew it was a Boots Riley show and was just enthralled. It touches on… It is a really cheeky way of touching on a lot of really important topics, but often hard to talk about topics and themes, and it’s kind of delightful to get through it. So, I’m a Virgo. I just binged Barry from season one through four. Henry Winkler was spectacular. And then just came off of Succession, too. The theme here is I really dark comedies. Yeah, really, really dark comedies are kind of my thing.

Lenny: And that first one was called I Am a Virgo, because I thought you were just saying you’re a Virgo.

Chris Miller: No, no. The name of the show is called I’m a Virgo. Yeah.

Lenny: Amazing. I will check that out. Okay. What’s a favorite interview question you like to ask candidates?

Chris Miller: I think it depends on what level of role that they’re interviewing for. I don’t really interview as many frontline PMs anymore, but I used to really like doing case study questions and really random ones too. I’d be like, “Tell me how many people crossed the Longfellow Bridge in a week.” And I could not care less what the actual number they arrived at was, but it’s more for me to observe what’s the array of data points that they can kind of start to collect in their mind to inform their calculus, and how close can they get to ballpark, and what’s their defense behind their thinking. And then just the process of watching people’s brains move in those moments is… You learn a lot about how they might operate as a product manager I think in those scenarios. I try not to overdo them, because I do think there’s a lot of inherent bias in some of those types of questions. And so trying to think of things that are really relatable to anybody who might be looking to work on a team that I’m leading is I think a requirement there.

But I would say the other question I really like to ask is, if the people that you most recently worked with were in a room and you weren’t there, how would they talk about you? One, it’s because sometimes I will reach out and get references, and so the extent to which that might actually be part of the interview process is very legitimate, but also I think it is usually very clear whether the person is taking an honest and introspective and self-aware approach to answering that question. And I like to see people being really self-aware, because I don’t think anybody ever comes in any situation perfect. I have a lot of rough edges to my personality that I think people have just learned to deal with over the years, but I try to be self-aware about them at the… If I can do nothing else, if I can’t change them, at least recognize them and do what I can to mitigate the blast radius.

And so I think just getting a sense of the EQ of a candidate and their self-awareness is really important for me because at the end of the day, if you’re in product, you can be the smartest person in the room, but if people don’t want to work with you, you’re probably not going to go very far.

Lenny: Do you have a favorite life motto that you come back to or you share with other people?

Chris Miller: The details matter.

Lenny: And that’s both in work and life, I imagine?

Chris Miller: Yeah, the details matter. The details matter. I read a cool interview with the product leadership team at Stripe, and one of the things they talk about is for their product managers, they want you to have taste. And it was a really kind of controversial thing to say because it was like, “Oh, that is so subjective. Who gets to decide what taste is?” Maybe that’s even biased to some extent.

And I think they had a super defensible answer about how they define taste, and taste in their opinion was to be so interested in something, it doesn’t matter what that thing is, where you can go deep enough in it to have a strong set of informed opinions. And that’s how they defined it. And they were almost ambivalent to what that thing that was, what the subject was. But having taste, having something that you were passionate about, that you have spent enough time learning and understanding and appreciating and critiquing and being frustrated with that you have a point of view that is potentially even polarizing is taste. Riding the fence is usually not taste. And so when I think about the details matter, that’s almost like a nod to taste. Obsess over the details of something, whether that be art, music, product, film, whatever. I care a lot about that.

Lenny: I love that. And that comes back to a lot of the things we’ve talked about of talking to customers, looking the data, actually having the firsthand information on what people need and what people want from your product.

Chris Miller: Yeah, absolutely.

Lenny: Okay. I’m just going to ask two more, and I’ll let you go. What is a favorite product that you’ve recently discovered that you love?

Chris Miller: I fell in love with golf right before the pandemic, but the pandemic really is when I lost my mind and was obsessed with golf. It was one of the few safe things that you could do outside that was social and less dangerous than getting a drink with your buddy at the bar. That’s the joke. It’s like men invented golf so they could go on walks with each other, and that’s essentially what kind of drove the interest in golf. And I also was horrible at it when I first started.

And so I think also as you get older and maybe you get more established in your career, or I’ve been in a product-led growth sort of lane for a while. You almost forget what it’s like to be really bad at something until you have a kid and then everything’s new and you’re failing every day.

But golf was a refreshing, consistent experience of frustration and inadequacy and just really embracing that and just waiting in it for a while knowing that it’s just going to take cycles and time to get better and better. It was something I got really addicted to, and so I tried to play golf whenever I can, and most recently I bought a Garmin watch, and that thing is just magical. You roll up to the first tee box, you look at your watch, it knows exactly where you are, which golf course. Sometimes it’ll even tell you which tees you’re at, because in golf sometimes you’re further back and sometimes you’re further ahead, and it tracks your swings, it tells you distances.

Lenny: That’s insane.

Chris Miller: It reads the greens for you.

Lenny: Wow. I just want to play golf just to use that watch.

Chris Miller: Oh my gosh, some of the guys that I golf with, a couple of them had one recently and I just was enthralled by it and I literally went home and ordered it that same day. And it’s been the coolest product or gadget that I bought in a while.

Lenny: Damn. I love it. And I was also thinking as you were talking about getting into golf connects back to your relentless curiosity and resilience that you look for in people that you hire. So clearly you have it yourself.

Final question, I believe you have a dog named Ferney, which is short for Fernet.

Chris Miller: Yes.

Lenny: Okay. So on that note, what is your favorite current cocktail, if it’s not just a shot of Fernet?

Chris Miller: The nightcap is always a shot of Fernet. Sometimes you might mix a little Coca-Cola with that. I think, where do they do that? Is that Spain?

Lenny: I have not heard of that.

Chris Miller: Or Argentina. I don’t know. It’s definitely a country that that’s a thing. My wife has been really into really high quality margaritas, made at home, and we’re big into Aperol Spritz in the summer, so I would say that that’s usually what dominates the happy hour rotation these days.

Lenny: I just had an Aperol. Is it Aperol? Aperol Spritz, right?

Chris Miller: Yeah. I’m not good at pronunciation. It’s probably one of those two.

Lenny: I just had that for the first time. It’s amazing. That’s going to be my new go-to.

Chris Miller: You had an Aperol Spritz for the first time recently?

Lenny: Yes. I didn’t know what that was.

Chris Miller: That was like the zeitgeist a couple summers ago and then there, oh man. There’s the other one too. The Negroni Sbagliatos are having a moment too. It’s like a Negroni with Prosecco. I forget.

Lenny: Ooh, that sounds amazing. There’s so much knowledge to be gained in this podcast episode. Chris, this was incredible. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out and maybe ask you a question or two. And two, how can listeners be useful to you?

Chris Miller: You can connect with me on LinkedIn. Shoot me a message. Christopher Miller. There’s a lot of Christopher Millers. I’m the one that looks like me, works for HubSpot. I have a Twitter. I don’t spend ton of time… X. I have an X account, but I don’t spend a lot of time on the app, formerly known as the bird app, but I’m on Instagram @millsyjoeyoung, which is a nod to one of my favorite old monster films, Mighty Joe Young. And so yeah, I’m on Instagram a bunch, too. That’s where you can find me.

Lenny: Then I know two other things that you wanted to share. One is that you advise on PLG and things like that, so maybe talk about that real briefly. And then also you’re hiring at HubSpot, or can people know about that?

Chris Miller: I definitely do a bit of angel investing and advising companies on the side, and I really enjoy it. I think there’s something really cool and awesome about getting to see fresh problems all the time and not necessarily being so laser focused on the sort of categories or verticals or target customers that you’re dealing with for 40 plus hours a week. And so it’s kind of refreshing to spend time with founders who are working on products in different categories and having different challenges at different stages of growth and being able to figure out how I can be a resource to them. And so if you’re looking for, if that sounds interesting to you, you’re a founder or head of product out there, definitely reach out and maybe opportunities for us to collaborate and maybe that can be a resource.

Lenny: Cool. And then on the hiring front, any specific roles you want people to know about that you might be hiring?

Chris Miller: There’ll definitely be more roles opening up in the fall, but I think most immediately I’ll be looking for a group product manager to work on the AI platform team that I’m leading.

Lenny: What a role.

Chris Miller: Yeah, it’s a great role with a fantastic team and a space that might be a little important these days. And so if you go to the HubSpot job site, that role should be there by the time this podcast is live. That role should definitely be up there.

Lenny: Amazing. Chris, thank you again for being here.

Chris Miller: Lenny, pleasure. Thank you for having me. This has been amazing.

Lenny: Bye, everyone.

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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