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

[00:00] like 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 like self-service. So we approached a team who owned it and we were like, are y'all working on this? 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. And so we took it and like immediately blew it up. And so that attitude of sort of saying [00:30] problem 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 look hungry, so let's keep feeding us, right? [00:48] 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. [00:56] Today, my guest is Chris Miller. Chris is VP of product for growth and AI at HubSpot. [01:02] Chris started as an ICPM at HubSpot, where he helped create their early growth team, [01:07] 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,

[01:37] 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, [02:07] 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 SOC 2, 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 [02:37] For a limited time, Lenny's podcast listeners get $1,000 off Vanta. Go to vanta.com slash Lenny. That's V-A-N-T-A dot com slash Lenny to learn more and to claim your discounts. Get started today.

[03:07] 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. [03:37] flexibility, 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 [04:07] to learn more. That's sidebar.com slash lenny. [04:15] Chris, thank you so much for being here and welcome to the podcast. I'm so excited to be on the podcast. Thank you, Lenny, for having me. It's going to be a lot of fun. [04:24] A huge thank you to Kyle Poyer for introducing us. [04:27] I've heard so many great things about you from so many great people, and so I'm really excited to be chatting. [04:33] And I wanted to start with your very unique role that you're in now at HubSpot.

[04:37] and it feels like it might be a sign of things to come for product leaders, [04:41] Your title, as far as I can tell, is VP of Product of... [04:44] growth and AI, [04:47] Can you just talk about what that... [04:49] is and how growth and AI relate in the context of HubSpot. [04:54] I've been leading PLG at HubSpot for several years now, and I recently took on the [05:00] AI leadership role. [05:01] It's a special place to be in in that I get to... [05:04] help lead HubSpot in terms of how we should be thinking about building the foundational technology to create [05:11] AI powered experiences and then also [05:14] lead the strategy of how we leverage those experiences to help [05:18] that B2B business builder [05:20] be way more successful using our platform than they might have been [05:24] you know, in years past. So it's a really cool [05:27] intersection point between those two things. There's a lot we can do there. [05:32] One thing I took away from what you just shared is that [05:35] 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. [05:42] And I'm going to try to pierce through your modesty, and I'm curious... [05:46] What is it that you think you've [05:48] done really well or been successful at that [05:50] 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. [05:58] So when I joined HubSpot in 2016, it was definitely like an element of timing that really worked in my favor. It was maybe like a year or so after

[06:07] HubSpot had launched their free CRM, which was like a big, [06:11] you know, 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, um, [06:21] what was going to happen after that, right? Like, how are we actually going to get [06:24] leverage and enterprise value out of this sort of [06:28] big [06:30] enormous piece of free software we just put into into the universe right [06:35] And I think the pedigree of product manager at HubSpot at that time was also a bit different. There were folks who... [06:42] maybe started their time at HubSpot and support. [06:45] And so intimately familiar with [06:49] the product and with customers, you know, some of these [06:52] people had closed thousands of support tickets. [06:56] And my background was a bit different. I was actually less of a feature PM and I was sort of more of a [07:01] growth PM in my DNA. And so I sort of looked at this [07:05] through a completely different lens and [07:07] I just understood that what we were trying to actually do was [07:11] product-led growth, but we didn't really have the [07:14] shared vocabulary to call it that. Right. And so I think [07:17] 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. [07:27] maybe based on the titles that I had at the time, [07:30] I wasn't sort of inherently given a seat at the table and sort of really pushed my way into some of these conversations. [07:36] and then was eventually invited to them, right? And so, just always had an interest in,

[07:41] driving a strategy that was a click or two higher than maybe what my immediate team was [07:47] focus on and was always curious about how other parts of the business function. Like I used to spend a lot of time, [07:53] sitting on the sales floor, just going into the other buildings and talking to other folks, working on different parts of the business. And [08:00] And that's part of maybe [08:01] the serendipity that I miss about being in person, which is that you might just discover something from [08:07] 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." [08:12] So you absorb a bunch of context around [08:15] how pieces of the business are connected and you can start to [08:19] really widen your aperture in terms of the size of opportunities that might be in front of you that maybe you would have missed if you would have been so heads down on execution work. [08:26] And so I think that 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. [08:34] Hard to do those serendipitous watercolor chats in these remote hybrid times, huh? [08:38] Yeah, everything's so... [08:40] scheduled and tightly scheduled and you're bouncing from zoom to zoom and you know obviously [08:45] HubSpot has embraced hybrid and there's a ton of benefit to it. In fact, you know, [08:51] I was a new dad when I came back to work and my son wasn't in daycare. And so [08:56] It was so cool to just be able to pop out in between meetings and play with them for a few minutes just to go back. And you don't get that when you're in the office all day. So. [09:03] Definitely a lot of upside, but certainly... [09:06] You've got to be a little bit more creative in terms of the serendipitous knowledge sharing, the osmosis learning, and just context sharing that happens more organically when everybody's sharing the same physical space.

[09:17] You talked about how [09:18] Some of your early success was taking risks and being in meetings maybe you shouldn't be in. [09:23] Is there an example or a story that comes to mind of doing that, where you kind of took a risk early on? [09:27] being kind of a European might have spot and [09:29] or something that worked out really well, surprisingly. [09:32] this is a funny story for anybody. It helps about listening. I, [09:37] I apologize in retrospect for this, but there was a time where [09:42] we were having a lot of debates about [09:44] around pricing and packaging and, you know, we'll get into this, but [09:49] our go to market model and sort of [09:51] where we play in the addressable market [09:54] 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? [10:04] And we were trying to figure out how to simplify, simplify, simplify and [10:08] At the time, I was an IC, individual contributing PM. So who am I to sort of [10:13] have a point of 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, [10:25] part of a triad and we sort of both had a similar school of thought in terms of [10:30] what the pricing and packaging could be. [10:32] And we were over in Dublin, where we have our European headquarters and... [10:38] there was a party happening at... [10:40] 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

[10:47] And we ran into the COO at the time. [10:51] And out of the blue, I think he had asked us what we thought about [10:56] pricing and packaging. It was sort of one of those funny you should ask moments. Right. And so we ended up [11:02] kind of pitching in the midst of [11:05] Pints being sort of handed out, you know, [11:07] every which way you turn, [11:10] this vision for a completely different [11:12] where you might approach pricing and packaging, [11:15] And he was pretty intrigued. And he said, why don't you come to the next executive meeting and... [11:20] and pitch us on it. [11:22] I think that meeting was maybe a couple of weeks away. And so we looked at each other. We were like, oh, [11:26] I [11:26] Not exactly what we expected in terms of, I think, people welcoming [11:31] maybe a contrarian point of view at that moment in time. And so we sort of [11:35] were invited into this meeting with folks that we generally don't get to spend a lot of time with. [11:39] to pitch this thing that swam a little bit upstream and we ultimately didn't [11:44] go full steam ahead down that path. I think a lot of elements [11:48] of what we pitched have made their way over time into HubSpot's pricing and packaging, but it's certainly... [11:53] I think opened the door... [11:55] for us and for me, for myself, certainly for me, [12:00] to, uh, [12:01] be welcomed back into that room in the future and to be able to contribute ideas towards important decisions, you know? [12:08] I love that it's another example of serendipity and just running into people. Yeah. Also, I think it's a really good example of just how important it is for PMs to be proactive.

[12:18] And... [12:19] think ahead and not just kind of rely on people coming to you asking you for [12:23] your advice and getting invited to rooms. [12:26] I feel like so much of success in the product leadership role is [12:29] just like suggesting great ideas, being ahead of [12:32] where people are and having the answers. Like you had the answer right there in the moment, right? Because you did the work ahead of time. [12:38] Is that something you find as well, that that [12:40] ends up being really important. [12:42] Yeah. [12:44] One of the traits that I look for in... [12:49] PMs that I... [12:51] higher onto my teams. And also when I think back to the people that I've learned a lot from working with over the years, [12:59] One of the common [13:01] behaviors or traits is like relentless curiosity. [13:05] this like insatiable desire to understand things and a lack of fear in the [13:12] 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, [13:19] bring that to the table [13:21] 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 may be a member of. [13:30] Are there any other traits in that list of traits you look for that you think are really important that maybe other people don't focus on? [13:37] Yeah, Relentless Curiosity is probably my number one. My number two would probably be... [13:43] resilience, [13:44] Specifically if you're working in growth, I think if you're doing growth things,

[13:50] Right. Right? Like if you're doing... [13:52] product-led growth the right way, [13:54] then you're trying to balance the science of, you know, and sort of taking like a [13:59] somewhat hygienic approach to validating assumptions and hypotheses with [14:04] 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. [14:10] And when you're doing that, [14:12] you're going to fail more than you're going to be successful along the way, right? [14:16] And if you're not resilient, that can be really demotivating, right? Like, I think there's a [14:22] a stat that some [14:23] you know, growth [14:25] person put out there years ago, which is that like, [14:28] on average, [14:29] only 20 to 30% of... [14:32] experiments a growth team runs might be successful. So that means like, [14:35] 70 to 80% of the time, you're... [14:38] you're not putting numbers on the board and you're extracting learnings, hopefully that you can apply [14:42] 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. [14:49] which can sometimes look like making bets that are too small and too insignificant to matter, right? [14:55] if your sort of primary modality of [14:58] Product-led growth work is experiment-driven product development. [15:02] and you're hitting more than like 30, 40% of the time, you're thinking too small, right? And so that resiliency piece is certainly important in my mind. [15:11] Coachability is another one. [15:15] In the sense that I still think that the sort of [15:18] 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

[15:30] 10 years of experience doing PLG. I think that's mostly an unreasonable ask, but [15:35] It can certainly be taught. [15:36] And even if you do have some experience doing PLG work, it's important to know that [15:42] what that work is, [15:44] is going to look like is going to potentially vary in a meaningful way from [15:48] shop to shop. And so being [15:51] coachable and adaptable to whatever the [15:55] context is of the business or problem space that you're working on, I think is an important trait that I look for in [16:01] and 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, [16:13] Growth might not be for you, right? Like I think the best growth, [16:18] like product leaders and growth minds that I've that I've worked with over the years or have [16:23] had the, uh, [16:25] The [16:26] the privilege of learning from over the years. Like, I think the thing that I that I noticed about them is they are almost like [16:32] ambivalent to the solution and certainly ambivalent to like how complex a solution may or may not be. [16:38] and sort of taking like little to no pleasure or pride in the complexity of a solution so long that it delivers [16:45] the outcome that the business and your customers need, I think, is a really cool trait. And I kind of like categorize that under creativity. [16:53] You mentioned this phrase "relentless curiosity" and it made me think about [16:56] a story I read about you where the way you got into product management was [17:00] You were at some startup.

[17:01] And the [17:02] The founder was just like, [17:04] I've read that the cure to all our problems is going to be hiring product manager. [17:07] And you heard that and you Googled, what is product management? [17:11] And then you asked them, can I do that? [17:13] And that's how you got into the role. [17:15] So first of all, is that true? And second of all, [17:17] What's your advice to people trying to get into product management and any lessons from that experience? So first, yes, that is 100% true. That is how I stumbled into product management. [17:27] product management. So I appreciate all the folks who took a shot on me back then. But [17:32] But yeah, I mean, this was at a time where I would say product management as a function was definitely not ubiquitous across tech. Like there was a lot more. [17:40] at least in the world that I was in, a lot more of like a [17:43] standard waterfall approach to building products with a lot of like middle layers and engineering managers and really knowing who [17:49] had the job of like owning the problem from a customer's point of view. [17:53] And so... [17:54] There wasn't a ton... [17:56] of content out there and weren't even a ton of people [17:59] in the city at the time that I could really talk to to sort of learn. And so a lot of what I did was scrape my knees through the first years and a lot of like painful trial and error. And then, you know, eventually, I think. [18:10] there's a lot more energy and an interest around the, [18:12] the [18:13] around the trade craft and the function. And so I think... [18:16] It's much easier today for someone to [18:18] learn the fundamentals of product management without necessarily needing to do it [18:24] via like trial by fire. [18:26] My, uh, [18:27] advice to folks who are interested in like, [18:30] breaking into product management specifically is,

[18:34] focus, [18:36] A few things. One, focus on [18:38] 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. [18:47] the best talent out there, right? [18:49] But I think what you may often give up in those instances is, [18:53] you know, [18:54] structure to your own sort of professional development and [18:58] 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 and can actually like [19:07] wisdom share because truthfully, [19:09] It looks different in every company. And so it is one of those functions I do believe that [19:14] taking a truly academic approach towards [19:18] upskilling, [19:19] has fairly diminishing returns because it's tough [19:23] to field curveballs in a classroom, right? And so choosing where you want to break in is almost as important as choosing that you want to break in in the first place. Like, [19:34] thinking about who you're going to be reporting to, thinking about, [19:36] what's the track record of success for people at that company breaking into product management, trying to, [19:41] I think five years in advance to work backwards. [19:44] I think are all sort of important thought exercises along the way. [19:47] I would also say that if you're already at a shop, you know, where you are working a different function and you're sort of like product curious. Right. [19:53] that go, [19:54] Go. [19:55] Talk to the PMs. And what I'm gonna say is, 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.

[20:05] and do a little bit of volunteer labor, even if that's just shadowing, right? Because I think just getting that context and understanding [20:12] the sort of rhythm of how a team works [20:15] ideates and defines problems and prioritizes and ships software. [20:19] is the experience that's going to be the most important, because a lot of product management is also managing personalities and figuring out [20:26] how people want to work [20:27] with you and figuring out how you work for them. And so, you know, just getting that hands-on, [20:34] hands-on experience or at least direct sightline into sort of 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 [20:46] You know, [20:47] 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. [20:53] is willing to gamble some [20:55] some professional and [20:57] political capital on you [20:59] to get your foot into the door, even though you might not have any formal experience on your resume. [21:03] There's so much stuff that super resonates. [21:06] 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 are going to love it. [21:16] Bring the donuts. Exactly. Yeah. [21:18] I must be old. I don't know that anybody uses bringing the donuts. No, we had Ken on the podcast. We talked about it. We asked, like, what is the digital version of that when everyone's working remote? I think that's something that even if you're a brand EPM, you come across. [21:30] soon enough. [21:31] And then the other piece there, I really love this metaphor of scraping your knees. [21:34] because I find that to be so important to becoming a...

[21:38] PM. [21:39] is you think you could just read these things, take some courses, and it's going to go... [21:43] You got this and you're not going to mess up. [21:45] But I find that messing up is so... [21:47] important in helping to learn to do the job because like you said there's relationships and [21:52] 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. [22:00] So, [22:01] So I super agree with that. [22:04] Even though you said it's easier not to... [22:05] Learn to be a PM. It's still, I think, important. [22:08] to scrape your knees a number of times for you to actually learn to do the job. [22:11] Mm-hmm. [22:12] Thank you. [22:13] 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... [22:21] Oh, that was really helpful, other than just doing it, messing up. [22:24] sometimes getting it right. [22:26] Yeah. [22:26] So, [22:28] My [22:29] first [22:30] product management, [22:32] sort of like [22:34] job slash mission [22:36] was working on a... [22:39] B2B2C products and [22:42] There's a lot of unique challenges that came with that. You know, our customer was not the end user of our product. [22:49] We sold into institutions who then white labeled our product and then resold it to [22:54] the end customer and [22:57] So at the end of the day, [22:58] our customers own the relationship with the end user and not us. And so... [23:05] The challenges that that created were [23:07] that there was a lot of distance between us and the voice of the customer.

[23:11] or the voice of the end user, and we ended up building a lot of things [23:15] to satisfy [23:16] the buyer and the customer, but not necessarily the end user. [23:20] 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 people. [23:27] the person using it at the end of the day or provide sort of like, [23:30] magical value. [23:32] And so I think I probably shipped a lot of bad product those years. If I'm being completely honest, like I don't know that I would look back at. [23:38] what I shipped back then or what we shipped back then and sort of, [23:42] say, like, you know, they were the best possible solutions, the best possible product. [23:46] It wasn't until I got my second product management job where I, [23:51] it really was an inflection point where I was like, Oh, [23:54] God, this is what this is supposed to... [23:56] Look and feel like. Where was that? [23:58] I was working at a fitness technology company and [24:03] the person who [24:05] really [24:06] I would say, [24:08] change my entire paradigm of what product management [24:11] is supposed to be, [24:13] Someone I know you know, Farid Mosavat, who I believe was on the pod last October. Shout out to Farid if you're listening. I love Farid. [24:21] good friend and mentor and really... [24:24] helped me level up. And what was interesting about [24:28] those years is... [24:30] It was the first time I'd really gotten to... [24:32] work on a product where [24:35] it was a, [24:36] Freemium B2C. [24:38] run tracking app. And so we spent a lot of time talking to users

[24:43] directly and like a lot of like gorilla user research techniques like literally sometimes going outside and just like talking to runners and passing to understand sort of like what were the challenges. [24:53] and finding motivation and sort of, [24:56] Why do they choose? [24:57] running assistance, running applications in the first place. And, you know, so just that, that, [25:02] having that deep connection to the customer, [25:05] and not feeling like you're being kept at arm's distance was eye opening. I was like, oh, I didn't know that it could be like this. And then the second thing, [25:13] that we had at our disposal that changed the game for me [25:17] was access to [25:20] a huge... [25:22] user data set. And so having data at scale to drive decisions, being able to know that if we [25:28] make a change, we can prove causation from like a business impact standpoint or a customer [25:35] 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, you know, they land on Oz and all of a sudden everything's in technicolor and you're like, [25:50] oh my gosh, I can actually make informed decisions [25:54] about what I'm shipping, right? [25:57] Having a level of rigor around that and really... [26:00] being forced to articulate [26:02] a hypothesis and [26:04] have a point of view on what the outcomes might be before you actually build something. [26:10] we're all sort of [26:11] Um, [26:12] I would say behaviors and just like a philosophy around product discipline that I learned from

[26:19] Farid and that group of folks that I worked with closely during those years. And that was, I think, the... [26:26] I consider that to be when I really became a product manager. [26:30] There's two things I want to highlight there that, again, super resonate. [26:33] One is just-- [26:34] Whenever I talk to customers, [26:36] I always like, I'm like, why don't I do this more often? [26:39] Yeah. 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." [26:50] And so I think it's just if you're listening, you're just like... [26:53] maybe just go talk to a customer today. Talk to customers and you know, we also learned a lot from talking to people who [27:00] We wanted to be customers, but we're not. Right. And people who had either broken up with our product or. [27:06] evaluated it and never fell in love with it in the first place. And so, [27:09] I think every PM struggles with [27:12] time management and it feels like you need 60 hours in a day to get through your weekly [27:18] checklist or 60 hours in a week, excuse me. But finding time to just talk to people [27:23] 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... [27:31] tend to [27:32] really enjoy my conversations with people who [27:35] decided not to use HubSpot and to really try to unpack [27:39] what drove that decision was it as calculated as i think sometimes we can all [27:43] maybe assume that some of these decisions are. And then you often learn that like, there's sometimes kind of emotional, like really instinctual and visceral and maybe connected to brands more than they even connected the product. And there's a lot of like,

[27:56] things that I think when you're in the proverbial digital conference room with your team trying to [28:01] understand what makes your users tick, you're just like, [28:04] We're actually just [28:06] We're illogical humans at the end of the day at our core, right? And, like, that all rides on decisions people make. [28:11] in the day-to-day and it doesn't [28:13] change necessarily when they're engaging with your product as much as we love it [28:17] to be perfect science so that we can [28:19] you know, [28:20] moneyball the system, if you will. [28:23] That reminds me of a story where we were doing some user research on [28:27] a booking... [28:28] feature within Airbnb, and we went to Paris to do these really in-depth [28:32] user research studies were like behind one way mirrors and all that stuff. [28:35] and we were trying to figure out why [28:37] hosts weren't connecting Facebook to their account. This is like [28:40] five, six years ago. [28:42] 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. [28:54] But look at all this power you get. No, I don't care. [28:57] I don't trust it. [28:57] Yeah. [28:58] Yeah, that's why talking to customers is so... [29:02] Like you could have all the 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 will never explain the why behind [29:10] a behavior that, you know, [29:12] you can track through events firing. And so that's why that sort of, [29:16] proximity to the customer and that [29:19] directing that sort of relentless curiosity towards the sort of, [29:23] Qualitative stuff is so, so important because you just learn things that

[29:27] I just, [29:27] sometimes really unintuitive for our blind spots because we're often not [29:32] the people we're building product for. [29:34] Absolutely. I want to shift [29:36] Talking about HubSpot the business, but one more last thing I wanted to highlight from what you just shared, which is a really good... [29:41] Insight is... [29:42] you shared that your biggest inflection in your career was a manager, Fareed in this case, who helped you kind of learn the craft and [29:49] and develop your skills. And that's the exact experience I had too. Just like one specific manager [29:53] changed everything for me. [29:54] And that feels like a recurring theme to a lot of people, just having one person that really [29:59] spends the time to help you learn and correct you when you're making mistakes and all that [30:03] So, [30:04] If folks are wondering maybe why am I not [30:06] learning enough or [30:07] Why is my cure stagnating? [30:09] See if you can just find, you know, easier said than done. [30:12] but oftentimes it just takes one person to change everything. It gets in a sort of, [30:16] a conversation about [30:17] you know the difference between a manager and a mentor versus a sponsor and an advocate [30:23] 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, [30:28] who [30:30] the time that they... [30:32] donated to me, the time that they volunteered [30:35] to me and for me, [30:38] Calling them mentors, I think, sells what they were. [30:41] very short. And I would actually describe those folks as being like sponsors and advocates, people who are willing to [30:49] put up capital, right? Whether that's professional, social, [30:52] Capital... [30:53] to bet on you. [30:56] I mean, truth be told,

[30:57] When I interviewed with Fareed that first time, [31:01] I think back to the interview, and I think I bombed it. I don't think I actually don't think I would have hired me back then. I actually think. [31:06] 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. [31:11] And I imagine that [31:15] There was something in there. [31:17] Where... [31:18] The decision maker who was freed said, [31:21] 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. [31:28] is what really... [31:29] matters and finding people who are willing to, again, [31:32] put something up for you, whether that be [31:36] Whatever kind of capital it is, when I think about [31:38] true [31:40] gasoline on the career fire, it's finding [31:44] mentors, but it's also finding sponsors and advocates. [31:48] Is there anything that you think you did right to help find mentors and sponsors and advocates? [31:53] For people that are thinking about, like, hey, I need this. How do I help myself in the same way? [31:59] Is there something you did that helped people get excited to help you? [32:02] Something I think [32:03] I certainly continue to work on, but really, [32:08] putting ego aside and embracing [32:12] not knowing [32:13] stuff and embracing not being good at stuff. [32:16] and not feeling self-conscious about that, [32:18] and letting the desire to... [32:21] be the best at something or be, or at least be great at something, [32:25] overpower the [32:27] fear of being inadequate at something. And I played sports growing up, and so I like being coached. I can take hard feedback.

[32:35] And I like it because if I get better feedback, then... [32:38] the people I'm competing against, I think I can beat them right over time if I work hard enough. And so I think just like taking that mentality, [32:44] with me [32:45] into product management, I think has [32:48] helped me [32:50] build bridges with people who... [32:52] don't owe me anything, right? People who don't necessarily need to be invested in [32:56] and me. [32:58] at all. [32:59] but who might get the light 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 that's [33:07] What's within my control is how I can show up. [33:10] in those in the context of those relationships and and sort of really embrace [33:14] even the hardest, like, [33:16] ugliest feedback and hope that I can extract something from it that'll make me better at the end of the day. [33:22] I love that advice. [33:24] 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. [33:31] 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. [33:39] Yeah, shout out Jules. Jules is also someone who has been generous with me in the past in terms of giving time when I've needed help. [33:48] Also a great episode you did with Jules. [33:51] So many people have said what you just said about Jules, about how helpful he's been to them. [33:55] Clearly a class act to that guy. Maybe we'll have to bring him back. We'd love that. [34:00] Yeah, V2Jules. [34:02] So, let's shift to HubSpot the business, which is a pretty incredible success story from my notes.

[34:11] It's worth something like $30 billion now as a business. It's been around for 17 years. [34:16] Still growing, I think, something like 30% year over year. [34:19] And most interestingly, Okta put out this really interesting report recently where they looked at [34:23] their data of what [34:24] tools people are using to authenticate with. [34:27] And they... [34:28] They showed that basically HubSpot is maybe the fifth fastest growing software product in the world. [34:32] I don't know if it's true, but [34:34] Feels true, because all the other companies... [34:36] Makes sense there. So you don't have to confirm or deny this. [34:40] But clearly things are going great. A HubSpot... [34:42] I'm curious just what makes [34:44] HubSpot's so special and unique and successful. [34:47] that's specifically unique to HubSpot versus other companies. There's a lot in there. I can speak to [34:54] the things that have resonated most deeply with me in my time there. [35:00] The first is... [35:02] legitimate customer obsession. [35:05] It's not marketing. It's legitimate, right? I've witnessed fierce and passionate debates [35:12] internally, [35:14] that [35:15] the root [35:16] of what [35:17] people in the debate were really trying to unpack was what was the best thing for the customer [35:21] And so [35:22] really having that be central to [35:26] our dogma and how we think about the business and why the company exists in the first place. [35:34] really walking the walk there. [35:36] is something that I don't think [35:37] 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

[35:44] 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 [35:52] that customer centricity really baked into the DNA of the company makes the [35:57] those decisions, maybe not easier, but at least you can have [36:00] more conviction, more conviction, [36:02] around the why behind the decision at the end of the day. [36:05] Another thing that I think makes HubSpot [36:07] Before you actually move on to the next one, I want to spend a little time on this one. [36:10] 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 things. [36:18] or revenue 1%, but it's not really going to make the customer's life easier. [36:23] How do you actually make this real? And there may be an example where you have to trade off [36:27] 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. [36:33] One, I think that's a really fantastic [36:36] maybe not counterpoint, but thing to call out, [36:39] My point of view here is that oftentimes it's a function of [36:43] what's the time horizon that [36:46] the company uses as their sort of baseline for, [36:51] assessing... [36:53] decisions, right? [36:54] And typically when you're making decisions [36:58] that [36:59] could be described as like, [37:01] hostile towards your customers, but a net positive for the business, you're [37:06] probably not thinking long term enough, right? Because [37:09] There's no possible way [37:11] unless you are completely cloner to market and there is no competition whatsoever,

[37:16] that you could continually be [37:19] hostile towards your customers and [37:22] and grow, right? Like at some point that's going to catch up. And so, [37:26] Oftentimes, I think it's the tension of what do we need to do in the short term to survive? [37:31] versus [37:32] long-term, where are we going? What's the path that we're actually charting? [37:36] is I think the true tension, but if you're making [37:39] decisions that might have lasting impact that are customer hostile. I think that's a really [37:45] dangerous path to kind of go down. And so, [37:48] Having, I think, the discipline or the bravery or the courage, whatever, to, I think, focus on [37:57] not necessarily tomorrow or the day after and really think about like, [38:01] two, three, four years from now, what are the outcomes we're trying to drive [38:05] and what are the decisions we need to make in the interim that are going to lead to that outcome. [38:09] If you... [38:11] Stick to that [38:13] sort of framework or first principle is a better way to describe it and i i think you'll often end up [38:18] arriving at the conclusion that [38:20] doing the thing that's right for customers at the end of the day is the right decision [38:24] Is there... [38:25] something in the way you operate that helps you [38:28] systemize that like in your experiment plan or [38:31] product specs or experiment results. [38:33] Or is there a story of something where you're just like, [38:35] shipped something [38:36] But [38:37] shows this customer obsession to make it even more [38:40] concrete for listeners. [38:41] 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,

[38:49] it's around like, [38:51] forcing specificity of language. [38:55] For example, you look at a lot of standard... [38:59] documentation for features or experiments whatever [39:03] And one of the first things it's like, outline the problem. [39:07] 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... [39:15] an efficiency problem, right? Like describe the nature of the problem [39:19] and parse it out. Because if there's, [39:22] Generally, like speaking, if there's a business problem, right? [39:25] you might do the thought exercise of asking like, well, why hasn't that problem solved itself? Like what's the actual customer problem? [39:31] that is leading to the downstream, like negative thing that's happening to the business. And if we can actually like, [39:35] create some daylight between those two things conceptually. [39:38] we can avoid making the mistake of, [39:41] trying to solve a business problem in a way that leads to [39:44] a bad outcome for the customer at the end of the day, [39:47] And I think also... [39:49] creating a system that makes it easy for PMs to [39:54] 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, [40:01] downstream things and if we can kind of like call those things out and just keep asking like why why [40:07] to sort of justify some of the direction you want to go in and then keep asking what, what, what? [40:12] in terms of [40:13] what's the sort of like true glass radius and domino effect of these decisions [40:18] is the approach that we take at HubSpot, in my teams at least.

[40:23] Awesome. Okay, so I cut you off in this one... [40:26] bullet points so far, so let's keep going. [40:29] Yeah, so we're talking about the things that make HubSpot special. So customer obsession is definitely one. [40:35] I think where we play in the market too, like, you know, being a company that has been comfortable [40:41] sort of staying in the mid-market, SMB mid-market space, and like resisting the temptation to try to crawl [40:47] up into enterprise software. [40:49] I think makes us special. [40:50] And one of the things that's actually really straightforward, which is that a lot of enterprise software companies [40:56] a lot of your revenue is tied up in like, [40:58] a small subset of customers. And I think what can happen there [41:02] is if those customers decide that [41:04] they want you to build something, [41:05] and they're willing to sort of threaten their business over it. [41:08] then [41:09] you'll end up building it. And is that necessarily the thing that is going to serve all your customers? [41:14] best? Probably not. Are you going to end up having to build and maintain [41:18] Bespoke software for one customer, probably. [41:21] And don't get me wrong, I think there's a lot of-- [41:23] product folks out there who enjoy that modality of work. I'm not one of them. And so, [41:28] By playing in the mid-market, [41:31] It means our revenue is distributed more evenly across our entire install base. [41:35] which means that there's no single customer who can hold us hostage, really. [41:40] But what that does is, with great power comes great responsibility, I think. [41:44] What that does is the forcing function of ensuring that [41:47] the decisions that we make [41:49] are a net benefit for the largest swath of customers possible. And I think it really is a guiding light behind some of our

[41:56] decisions around like connected experience and, [41:59] usability and user experience. And so playing in the mid-market, I think, affords us to be able to do that. [42:06] So I think that's another thing that makes us special for a company of our size. [42:10] 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. [42:17] I don't know if people have heard of that. What is that? [42:19] Yeah, Dharmesh, you know, our co-founder, one of our fearless leaders, Dharmesh, one of the things he [42:24] most famously did early on is [42:27] he published the HubSpot culture code externally. And you can Google it and find it anywhere. I think a lot of companies sort of replicated that over the years. [42:34] But by being sort of like really open and transparent about the culture, both internally and externally, I think, [42:39] One, internally it creates like [42:41] alignment and it gives [42:43] Everyone's something to point to [42:46] to sort of enforce, like, why do we choose to work with each other the way that we work with each other? Right. [42:51] 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. [42:57] 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, [43:03] and I think a lot of quality people [43:06] crave a lot of the things that are sort of codified in our culture. [43:10] humility, empathy, [43:13] Adaptability, remarkability, transparency are sort of all things I think people take quite seriously. [43:19] And so being really open and honest about that and being willing to sort of pressure test it [43:24] on a regular basis. [43:26] Is this still a company we want to be? We're growing really fast. What has changed? What conditions are still...

[43:33] able to be supported with the culture we have codified today? What amendments might we need to make in terms of, [43:38] who we want to represent ourselves to be to our customers, and how we want to work with each other. [43:45] and investing in that, like hiring really good people that can help us scale that, I think, [43:49] is something that makes HubSpot really special. [43:52] Amazing. I'm reading the culture code on the side here. [43:55] And there's these little quotes that are really sweet. I really like this one. [43:59] Solve for the customer, not just [44:01] their happiness, but also their success. Yes. [44:04] Wise. [44:34] production in a matter of days and save countless weeks building custom integrations, letting you get back to building your core product. Merge's integrations speed up the product development process for customers like Ramp, Drata, and many of their fast-growing and established companies, allowing them to test their features at scale without having to worry about a never-ending integrations roadmap. Save your engineers countless hours, hit your growth targets, and expedite your sales cycle by making integration offerings your competitive advantage with Merge.

[45:04] slash Lenny to get started and integrate up to three customers for free. [45:10] Is there anything really fun about the culture? Like a fun thing that you all do that's like... [45:15] quirky hop spot ritual [45:17] Yeah, there's a ton. Although, you know, I think like [45:19] There's definitely... [45:21] a very legitimate, [45:23] school of thought around... [45:26] how like culture can both contribute to, [45:30] inclusion but also be a headwind to inclusion right 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 [45:44] where we were all [45:45] sort of working in the same physical space. And so there's a lot of like inside jokes and [45:50] Sometimes the [45:52] The things are rooted in very... [45:54] specific quirks of specific individuals who may not even be at the company anymore [45:58] And so if you're someone who's joined the company in the past like two or three years and that [46:02] flies over your head, [46:04] 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 – [46:13] been considered part of HubSpot legacy culture, and really trying to, again, pressure test it. [46:17] does this continue to serve us today? And if not, like, [46:20] we should be really comfortable [46:22] of letting it go. 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. [46:31] during the pandemic and the TLDR is that it's kind of like an event for product and engineering.

[46:36] where travel kind of changed with the pandemic and people don't get to see each other in person as much. [46:41] 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 north america we fly to cambridge if you were in europe somewhere then we fly you to dublin and we kind of spend a week together and there's [46:55] it's not a ton of focus on just like classic productivity. There's like a ton of focus on, [47:00] building connections and like safety and just like getting to know people and who they are is like [47:04] as human beings, but also like, [47:06] damn, I forgot how much I miss whiteboarding. It's just like actually being able to get in a room with a physical whiteboard with people and work on some stuff. And so... [47:13] This is, I think, the second year in a row, or second or third, I don't remember, pandemic year is a really... [47:19] fog the brain that we've done it. And it's like one of the things I look most forward to every year is getting everybody in the same city to just hang out. [47:26] I love it. [47:27] Thank you. [47:28] peeking at these highlights, and they're really interesting. So [47:31] We're going to link to this culture code also in the [47:33] show notes if you want to check it out. [47:35] But anyway, let's focus on [47:37] how a plot grows. [47:39] And there's kind of two parts. In my mind, there's just like, how did it start and what worked really well? [47:43] You're actually on the inaugural team, I believe, of HubSpot's growth team. [47:47] And things worked out. Well done. [47:49] I'm curious, maybe just to start. [47:51] what you think you did so right. [47:54] early on in the history of HubSpot to help it [47:56] grow into the behemoth it has become what was kind of the early success elements that were key [48:02] I would say the early years of doing freemium and for the record,

[48:07] There's definitely like a... [48:10] an iteration of the growth team before I joined that, you know, really like Brian Balfour, [48:14] was the person who I would say, [48:17] injected that first [48:18] dose of like PLG DNA, uh, [48:21] into HubSpot. So shout out to Brian. I want to make sure he gets the credit that he's owed. Yeah, we're going to have him on the podcast at some point. It's in the works. Yeah, he's a legend. Brian's great. Absolute legend. [48:31] And so... [48:32] You know, [48:34] After Brian had left HubSpot, you know, it was a bit start and stop. And so when I joined and we sort of took another stab at it, [48:42] I think, [48:43] there are a few things we did. One in the beginning is we, [48:46] really... [48:48] had an aggressive mentality, an aggressive approach, I think, and by we, I mean the team, like the actual really small initial growth team. We tried not to be... [48:59] pedantic about where we were spending our time. And so we sort of [49:04] tossed our mission and charter out of the window. We said, "Cool, maybe on paper, [49:08] we were, I think, like the sales tool activation team. It was very like, you know... [49:13] Boutique. [49:13] Mission and Remit compared to like I think a lot of the other teams at HubSpot's Missions and Remit at the time, [49:21] But even though that's what we were supposed to be working on on paper, we were sort of like a [49:25] If we find something, [49:26] It looks like an opportunity. [49:28] and no one else in the business is thinking about it, [49:32] we're just going to try to fix it, right? We're going to ask for forgiveness rather than permission and start to call some plays and

[49:39] What that looked like was, at the time, a very small percentage of [49:44] I think HubSpot's subscription revenue would be described as like self-service, like people putting in their credit card. [49:50] and buying something. It was predominantly [49:53] product-driven [49:55] like leads, like PQLs. [49:57] And so we were literally sending everything to the sales team, which, you know, it was [50:01] playing revenue. [50:02] but certainly opportunities for efficiency, [50:05] because it was the first time we had really had a product [50:09] at a price point that could be transactional and not a highly considered purchase. And so [50:15] we were thinking about this and we were like, well, how does this work? Like, is there even a pricing page in that, in the product that people could, [50:22] you know, [50:23] actually buy something and we found it [50:25] But it had been neglected. It was sort of like, I think no one was sort of committing any code to that repository. [50:31] So we approached the team who owned it and we were like, [50:34] are y'all working on this? Right? Like, is this an active development? And they were like, nah, we're working on a bunch of other stuff. [50:39] We were like, can we take this? [50:41] And they were like, "Sure, if you want it, take it. Like it's one less code base for us to maintain." [50:47] And so we took it and... [50:49] immediately blew it up. We redesigned the whole thing. [50:52] focused on [50:53] discoverability, like how are people getting to this page, focusing on [50:57] desirability, like how are we talking about the value props of the things that [51:01] we're wanting to sell to customers to help them grow better. [51:04] And then thinking about doability or usability, like how do we actually just like remove the friction that's standing in the way,

[51:10] And so we did like a mad dash towards this outcome we wanted to drive. [51:15] And when we released it, [51:17] it worked right. Like it actually, it was actually like a step function change in the way that the, [51:22] It's physics of the business in the funnel. [51:24] really looked. I think that was probably a catalyst moment of everyone saying, oh, well, there might actually be something here. [51:31] And so that attitude of sort of saying that, like, [51:34] Every problem is our problem and sort of being willing to like really, [51:38] take a mentality of radical accountability and ownership mentality. [51:44] Help us. [51:45] 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. [51:54] And when you do that, I think the business, a business, [51:59] May... [52:00] get more comfortable putting more on your plate, right? And so it's like, we look hungry, so let's keep feeding us, right? And so, you know, over time, [52:08] Our remit expands and there's other things that we think are opportunities to gain leverage [52:13] for the business or deliver 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 [52:28] of our customers just like, [52:30] 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... [52:35] a sales engagement, right? And so it was really kind of like meeting the expectations of the modern software buyer in many ways.

[52:40] This sounds incredibly important. [52:42] Basically, your team turned [52:45] HuffSpot into a very product-led growth. [52:47] business, which feels very important in the history of HubSpot's growth. Would you consider what was there before where it was like, [52:54] the beginnings of self-service, but they had to talk to a salesperson. Would you consider that product-led? [52:58] Yes. Versus [52:59] Okay. And so how would you describe what the shift was in terms of the way the sales motion [53:04] and growth motion changed. [53:06] the go-to-market motions that we were working on [53:10] definitely fit under, I think, the broad umbrella of PLG. [53:14] But I don't think the culture of the company was necessarily... [53:19] explicit about like [53:20] being a PLG company. I don't think that's the way we talked about [53:24] who HubSpot was, and trust me, there were a bunch of other factors in here. I definitely, I won't say that our team [53:30] were like the sole driving force behind that shift in, [53:35] our strategy and approach, but certainly [53:37] the data that we were able to... [53:40] collect and the experiments we were able to run and the insights we were able to surface and the research we were able to [53:46] synthesize [53:48] it gave us conviction to double down on it for sure. And, [53:52] 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 [53:58] us wanting to become [54:00] more product. Again, think about it. I think any company [54:05] is probably searching for ways to operate more efficiently. And if your revenue is so, [54:10] tied to like

[54:11] go to market headcount, it gets really hard to scale the bigger you get. So I think there's an innate [54:16] desire to want to [54:18] be more non-linear in our growth, right? And I think [54:22] us arriving at the right place at the right time, [54:26] created... [54:28] sort of alignment around what the path forward could look like. 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 [54:39] 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. [54:47] And it sounds like you weren't like, we need to be more product led. It was more just how do we get [54:51] the sales [54:53] process more efficient and the motion of growth more efficient, and that emerged out of that. [54:58] 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, right? Like you asked, you know, [55:06] would I consider what we were doing product-led growth? And I think the answer is absolutely [55:11] but that's because a fallacy that people... [55:14] I think [55:16] 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. [55:22] maybe fall into the trap of is assuming that like in order to be a PLG company, that's, you can use that interchangeably with like being a fully self-service, [55:32] business or fully self-service go to market. I don't actually think that those things [55:36] are one and the same. I think that [55:38] Most companies, at least the larger, more successful ones that have sort of done amazing things,

[55:44] and are cornering their market or category, [55:46] that we would consider to be PLG companies, [55:49] have a bunch of humans working on really important things when they go to market. [55:54] And it's more of a hybrid motion. And I think it's less about [55:57] again, being sort of myopic about [55:59] your approach to PLG and sort of having it being really rooted in like [56:03] principles that are, I think, [56:05] very kind of like, [56:06] academic or conceptual in nature, but more sort of [56:09] being pragmatic and saying, "Okay, cool. [56:12] 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? [56:21] what's the packaging of our products? How do our customers decide? Is it a top down decision or a bottoms up decision? [56:29] how complex are our billing and subscription terms? Is this something that's going to be pretty transactional or something that's going to be fairly considered? [56:38] How comfortable is our target market with [56:41] the technology in our category? Are they, are we competing against non-consumption? Are we competing against, [56:46] competitors in the same category. And if you actually answer those questions, [56:50] And I think it may be obvious where I'm going with this, but based on the answer to those questions, [56:54] the conditions on the ground might lend themselves [56:57] to be more favorable to product-led growth and be more favorable to self-service, right? [57:01] 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 use Loom. It's so intuitive. [57:10] 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

[57:15] even Slack to some example, like Slack is extremely intuitive, right? Like you would throw someone in Slack and they'd use a product [57:21] in a similar paradigm and they can probably figure out the basics on their own. [57:25] there are some products that don't necessarily check those boxes. And so I think what you can do is kind of take a more modular approach [57:31] to PLG, [57:33] And it's like based on [57:35] how [57:36] A customer in the best case scenario might go from zero to one when it comes to activation and onboarding. [57:43] Do we need to have a human involved in that process at all or as a backstop? [57:47] 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. [57:55] if [57:56] that's not the case, then like go, 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, [58:04] Everything here for this line of business or this product line is going to be self-service. [58:10] without sort of being able to defend and contextualize why across the entire customer journey this makes sense. [58:16] And so, yeah, we have customers who come in through the product-led front door and, you [58:21] kick the tires on the product on their own and activate on the product on their own [58:25] But then when it comes time to buy the product, they want to talk to somebody. And there's legitimate reasons why. Right. Like there are maybe I.T. and security concerns that they need to get somebody on the phone for. [58:35] Maybe they're coming for a platform where data migration is a huge... [58:39] fear they have, and that's not something that's easy to do. [58:42] 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.

[58:48] And so to try to like [58:50] brute force that into a sort of self-service motion for every customer writ large [58:56] would be solving for your business's desires, not necessarily solving for the customer at the end of the day. [59:01] But we also sell them to different segments of customers that are [59:05] Maybe... [59:06] Digital natives, but not familiar with products in our category. [59:10] and [59:12] Maybe they're coming from not a competing product, but they're coming from a more rudimentary system like spreadsheets. I mean, we, I've, I've, [59:19] I've seen customers using Post-it notes to manage their deal pipeline. [59:26] the real old school way. And that like, that was sort of their locus of control for their sales team. Right. And so, [59:32] 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, [59:39] today's buyers that you need to put out. [59:41] You don't have to deal with the burden of a huge data migration [59:46] 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. [59:53] there's a ton of those customers that we never talked to in person. Right. And like, [59:58] That's awesome, too. And so being comfortable [1:00:00] with things not necessarily fitting into like clean boxes and seeing and, and, and having, you know, [1:00:06] 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. [1:00:13] is something that I think... [1:00:15] we embraced really early on. Like one of the first metrics that I had

[1:00:19] was... [1:00:20] activation rate, but it was also how much demand am I sending to the sales team? [1:00:23] And there was no like turf war about that, right? It's like, oh, that's net positive for people. If people are able to get help, [1:00:29] And a lot of questions that they have cannot be answered with the product today. [1:00:33] we should absolutely be proud to connect them with one of our awesome people in sales who can be like, [1:00:38] 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. [1:00:48] Okay. [1:00:48] Amazing. I think... [1:00:50] On the one hand, this could be a whole podcast that's just talking about your PLG learnings. It feels like HubSpot is one of the biggest success stories of transitioning more and more into PLG, at least at that point. [1:01:01] even though you're saying it was... [1:01:02] PLG early on, it feels like a huge... [1:01:04] shift to the business. [1:01:05] So I really like this framework you just shared of [1:01:08] If you're trying to [1:01:09] become more product-led. [1:01:11] Just think about the zero to one from [1:01:13] visit to activation. [1:01:15] And when does someone really have to talk to someone? And how do we [1:01:18] help them not have to talk to people in that moment. [1:01:21] So either in that direction or just broadly, if someone was trying to explore how do we become more product-led, [1:01:27] What are the first couple steps? [1:01:29] dives you would recommend they do to help them down that road. [1:01:34] First, I would ask, why do you want to be product-led? [1:01:38] what assumptions are you making in terms of why being product led [1:01:42] are going to 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. We can kind of get on the same page of what we're even talking about.

[1:01:52] How would you define it? Do you have like a rough... [1:01:54] You have an answer to that, just so people get a sense of what it probably means. [1:01:57] 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. [1:02:08] Awesome. [1:02:09] 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. [1:02:15] One example that I think is really normal, like, [1:02:18] a hardship circumstance where a customer needs to like, [1:02:22] and their relationship, right? Like every SaaS company deals with this. [1:02:27] Some take a [1:02:28] fully automated approach, but [1:02:30] most usually have some sort of escalation path that will result in a human having to like resolve this. Like, [1:02:35] doesn't make them any less product-led. I think every company at its core is having some humans behind the scenes. [1:02:41] interface with customers on things related to go to market, right? [1:02:44] But I think once defining that and getting on the same page about that, [1:02:48] I think you can learn a lot. And by the way, these are the normal conversations that I have with [1:02:53] founders all the time. I'm actually an operator in residence [1:02:56] at OpenView, and so I speak to a lot of their poor co's. [1:03:00] And this is usually the conversation that we end up having. And I think what's always interesting is like how different, [1:03:06] the sort of array of answers are when you ask that question. Some are like, oh, [1:03:10] It's about top of the funnel demand, right? Like we want to be more product led because we want more leads, we want more signups. [1:03:15] You're like, oh, okay. And that's like a very defensible reason, right? Like there's a lot of data that shows that freemium products are

[1:03:22] attract [1:03:23] a lot more top of the funnel demand than, you know, sales led go to market. [1:03:28] products do, right? [1:03:30] Some it might be [1:03:32] uh a matter of like constrained resources like we need we absolutely need to be more product led in this stage of the company because we simply cannot hire an army of like [1:03:42] implementation specialists and folks on the customer success side of the house to help every single customer at scale. [1:03:48] 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, right? [1:03:56] And so when you can kind of articulate the outcomes that you want to drive, [1:04:01] It helps. [1:04:03] triangulate [1:04:04] Where to begin? [1:04:06] Right. So if you are really focused on top of the funnel demand, [1:04:09] trying to do self-service checkout is a silly place to start, right? And so just like really [1:04:15] doing the fun exercise of articulating, like, why do you care about this? Like, why are you actually interested in this in the first place? [1:04:21] if you do this, what would change about your business? What assumptions are you making? And when you can actually list those things, 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. [1:04:34] Awesome. [1:04:35] Maybe a couple more questions along these lines, and then I just have a couple more questions I definitely want to ask. [1:04:40] When someone is trying to go in the direction of product-led, [1:04:43] growth, aka more self-service [1:04:46] And I guess maybe let me just ask, is that sort of how you think about equivalency of those two? Sure. [1:04:50] Okay. [1:04:51] What are maybe the most common mistakes they make that aren't as obvious?

[1:04:55] I mean, the number one mistake is like, [1:04:56] Hiring ahead of growth, giving them no resources and expecting them to pull a rabbit out of their hat. [1:05:03] I feel like every... [1:05:04] You know, every... [1:05:06] PLG veteran [1:05:07] has some joke that they tell about you know the poor head of growth who [1:05:12] has no tooling, no engineering cycles, no designer. [1:05:17] no access to data, and then our [1:05:20] handed a really scary big number and told to go move it. [1:05:24] I think that's a common mistake that has stood the test of time. Another one is [1:05:30] expecting really [1:05:33] quick turnaround and thinking of it, [1:05:36] the same way you might think about [1:05:39] Hiring a sales, like an incremental sales headcount. [1:05:42] which is that you're expecting near-term liquidity from that investment. [1:05:46] But when you're doing PLG, at its core, it's still R&D, right? Like you're still sort of... [1:05:52] planting seeds with the hope that, like, [1:05:54] over time, this is going to play out in the form of, like, durable, high-efficient growth. [1:05:59] But if you're expecting, you put a team on something, and then you want that team to sort of [1:06:05] have outsides impact. And sure, there's going to be low hanging fruit, but [1:06:08] I think just like not having the patience to [1:06:12] see the investment through and cutting bait, [1:06:14] Too early is another, I think, mistake. [1:06:18] some companies make [1:06:20] And then I also think that [1:06:23] Bad data hygiene is the other one. So not having taken a beat to...

[1:06:30] properly instrument their product messy data no real self-service way for people to access that data like [1:06:37] Having analyst bottlenecks can be a terrible position to be in. [1:06:42] And so, [1:06:44] Eating your veggies and getting your house in order from a data standpoint, I think, is – [1:06:48] a crucial first step because if you can't actually measure what's happening and like why [1:06:54] 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 Airbnb has. And it's like. [1:07:05] You can still do PLG, you just need to use different data. [1:07:08] the way we think about data is that like, quant data is just another form of data. [1:07:11] The same way experiment [1:07:12] results are just another data point. [1:07:14] You can learn a ton from just talking to customers. Like quality research is super duper important, right? [1:07:20] And so if you don't have data [1:07:22] to tell you exactly what every single person is doing in your product [1:07:25] in aggregate, [1:07:26] you can still talk to 10 customers and probably get a clear sense of what's happening and why it's happening. You wouldn't even get from the data. [1:07:33] So people sort of like... [1:07:34] getting demotivated, companies getting demotivated because they think they're too early to do PLG. It's like, you can still do PLG. PLG at its core is just [1:07:42] having your product [1:07:44] sell the value prop of what your business does, right? And you can still deliver on that without being able to stand up a very robust and sophisticated experimentation practice. [1:07:53] Kind of along those lines, but going even broader. [1:07:56] without disclosing trade secrets of how HubSpot works. [1:07:59] How would you describe the loop of growth of HubSpot?

[1:08:03] In the words of, you mentioned Brian Balfour and Fareed. [1:08:06] What's the growth loop of HubSpot, either now or recently? Just a simple way to think about how HubSpot grows. [1:08:12] Our loops are less tactical. In fact, if I'm being brutally honest, I think loops are kind of hard to achieve. [1:08:18] in B2B SaaS, right? Like, I think there's some examples of that, but I think like, [1:08:23] Some of the best loops come from like UGC, user generated content. I think like a lot of B2C, like community focused platforms can do loops really well. [1:08:31] I think if it's like B2B SaaS, it's like, [1:08:33] hard to find things that get loopy. [1:08:35] And, you know, this is me going... [1:08:37] I think all my reforged formings are going to be upset that I said that, but like, I think that's the truth. [1:08:42] When I think about the flywheel of Upspot, I think it's a much... [1:08:46] Like it's more of a macro flywheel, right? [1:08:48] And just to kind of lean into our own lingo, [1:08:51] It's really attract, engage, and delight. And so... [1:08:55] One of the principles that [1:08:57] guides our thinking and our strategy is like, [1:08:59] give value before you extract value. And I think that was at the core of inbound marketing at its inception of like outbound marketing was asking for, [1:09:08] something from customers or prospects before giving anything, [1:09:11] 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 [1:09:19] how that album sounds are going to come and stick around for more. And so, [1:09:22] In our pre-PLG days, it was content marketing and marketing. [1:09:26] white papers and listicles and e-books and things that people had to download [1:09:31] that we're really feeling the top of the funnel.

[1:09:35] And that is just taken out of the form with PLG. And so [1:09:39] You know, we intentionally put on a lot of free software. [1:09:42] And the idea is that this software is not [1:09:46] sort of gimmicky. It's not [1:09:47] designed to [1:09:50] 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. [1:09:56] But if they're engaging with it deeply enough, they're going to run into the limits of what that value is. [1:10:02] And if we've done our jobs and delivered what we believe we were supposed to deliver, [1:10:06] then the decision to purchase becomes a no-brainer. [1:10:10] And if they're delighted with, you know, [1:10:13] the experience of being a customer, [1:10:16] they're going to become advocates and they're going to become promoters and they're going to, [1:10:20] tell their peers, because what we also know is that a lot of [1:10:24] small business owners and even medium sized business owners, uh, [1:10:28] take a lot of guidance from their their community of peers, right? [1:10:31] And sometimes that's a digital community. Sometimes that's not. [1:10:34] And so anytime we win an advocate through delivering like an excellent [1:10:39] customer experience [1:10:40] they bring more people into the top of the funnel. And so it's a really like honest and I would say an honest macro loop in the sense, but like that's the way we think about our flywheel. [1:10:50] Man, this could be a whole other hour of a podcast just diving into this stuff. This is so good. You shared this interesting... [1:10:56] story that I wasn't aware of. HubSpot is kind of known for content and SEO [1:11:01] You search for anything and there's always a help spot. [1:11:03] article about it. [1:11:05] And so is what you're sharing here essentially, that was like a big part of the early days.

[1:11:10] 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 [1:11:19] the top funnel. [1:11:20] Yes, correct. [1:11:22] - Amazing. - I can't give a specific number, but a large percentage of our revenue [1:11:27] flows through the product and it's not necessarily like, [1:11:30] 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, [1:11:37] they spoke to somebody and then eventually became a customer. And that, that is like now pretty, [1:11:41] robust top of the funnel for the company. [1:11:44] So I think this is a really interesting story of just starting with one growth channel of SEO, essentially. [1:11:50] content marketing and then shifting to something else. Is there any lessons from that experience for people trying to kickstart their growth of [1:11:59] SEO versus the streaming approach. Is there anything there that just like this worked really well for us and you should probably try this? [1:12:05] or SEO kind of runs out [1:12:07] in this specific type of business. [1:12:10] 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 think are... [1:12:18] Bonafide legends at this point in terms of what they've been able to achieve at HubSpot and building that lead and sign up machine. [1:12:24] What I will say, [1:12:25] is... [1:12:26] Being really aggressive about experimenting with new channels is so important and diversifying your channel mix. [1:12:35] is so important because [1:12:38] things can change overnight and that might disrupt your entire funnel, right?

[1:12:43] a Google algorithm change. [1:12:45] can have a massive impact. If you're reliant on App Store optimization, [1:12:50] 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 [1:12:58] Losing sleep at night. [1:13:00] because it's unclear how this is going to impact like SEO writ large, right? Like if that's what fuels your entire business is like being on Google search result page, then like, [1:13:10] what's going to happen in this new sort of, [1:13:13] world we're about to enter. [1:13:15] So I think to the extent that you can... [1:13:17] not have your funnel be relying on a single or a couple of channels is really important. We're always testing [1:13:25] new channels, like one of the channels that [1:13:27] you know, we're spending some time experimenting with. [1:13:30] 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-- [1:13:36] Maybe Darmesh built this, the original one, but it was called Website Grader, right? And it was, 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. [1:13:49] Right. [1:13:50] It was definitely a one trick pony. [1:13:52] But what it did was it created an interesting conversation, which is like, OK, cool. Now that you have this information, what are you going to do about it? Right. [1:13:59] 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. Right. And that works for us. It worked really, really well. [1:14:07] And so we've done that play a few times, and it's something that we'll probably continue to do. Like, we have... [1:14:13] 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

[1:14:20] Build my persona generator. There's a couple of ones that [1:14:23] I can't talk about right now, but we'll learn a little bit about in a few weeks at inbound. But yeah, micro wraps, [1:14:29] are an exciting new channel for us and [1:14:32] You know, some will be successes, some will flop and will probably sunset them, but [1:14:37] Being willing to fail in the pursuit of finding new distribution channels is also really important. [1:14:44] That's an awesome insight. Is there a place people can go to find these micro-apps that you all have built? [1:14:48] There will be soon. [1:14:50] Oh, mysterious. [1:14:51] 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 doing fun stuff? [1:14:59] Very related to micro apps. I would say Chat Spot is actually, and for those who don't know what Chat Spot is, Chat Spot is [1:15:08] a bit of an AI co-pilot that Dharmesh built that has sort of been very positively received by both [1:15:14] HubSpot customers and non HubSpot customers alike. [1:15:17] And so that's something that we're... [1:15:19] you know, [1:15:20] wearing my AI hat, spending a lot of time thinking about sort of what direction do you want to go in the chat spot. [1:15:26] But again, it was something that we kind of put out in the universe to see what happens. And now it's like, oh, we're getting... [1:15:32] interesting amount of signups every month. Like, [1:15:35] Who would have guessed that, right? I don't think that that was... [1:15:38] That definitely wasn't on the roadmap a year ago, right? And I think being a 17-year-old, [1:15:42] SaaS company that can still operate with that sense of urgency and pace [1:15:47] helps a lot too. Like why wait to, [1:15:49] you know,

[1:15:50] get consensus on a decision when we can kind of [1:15:54] put something out there and then see [1:15:56] see what happens and see what the data says. Yeah, I was just going to say that. It feels like such a win-win-win. [1:16:01] including-- it's just like a-- [1:16:02] 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. [1:16:08] Yeah, 100%. [1:16:09] I love that. [1:16:11] Is there anything that just significantly accelerated growth in the last, I don't know, [1:16:15] number of years that was like, wow, this really changed the game. COVID. I mean, COVID was obviously... [1:16:22] challenging and awful on so many levels, but it was scary. Like it was super scary, right? We were all terrified. We didn't know what it meant for our jobs. Like, [1:16:30] 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 sort of how it was going to impact businesses? I think we were prepared for the worst. [1:16:47] And we actually caught a bit of the COVID tailwind and a lot of other businesses did because... [1:16:53] Companies who never had to think about digital marketing all of a sudden had to. [1:16:58] And it was urgent, right? It was a burning need for them to figure out how they were going to weather the storm. [1:17:05] And I think one of the things that HubSpot did [1:17:08] and this is one of the [1:17:09] sort of phrases we use internally is like never waste a good crisis. And so one of the things we leaned into was sort of like goodwill, [1:17:17] pricing and we lower the price on [1:17:20] some of our tools and created some temporary leniency around certain things.

[1:17:25] And just the removal of that friction [1:17:27] ended up being like a really, [1:17:29] interesting [1:17:30] tailwinds for the business and specifically for [1:17:33] 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, like I think if you would have looked at my bingo card, [1:17:45] in, you know, March of 2020. I don't know that I had that on the big old car. [1:17:49] I'm looking at the stock price in another window here and I could see what happened. That went great. And even, you know, it came down with the whole market, but... [1:17:57] It's coming right back up. [1:17:59] Okay, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready? [1:18:04] Yeah. [1:18:05] What are two or three books that you've recommended most to other people? [1:18:09] truthfully [1:18:11] 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, [1:18:22] Still, there's a book called Everybody Lies, and it's a book. [1:18:26] I believe the guy who wrote it [1:18:29] was a data scientist at Google. And, you know, the... [1:18:33] Part of the message is that everybody's a data scientist and really trying to like democratize the idea of like, [1:18:38] using data in your everyday lives to make decisions and like demystifying the idea of data science. But [1:18:43] the way he kind of does this is through... [1:18:46] comparing Google search data and like, you know, [1:18:50] what we know people [1:18:52] to be actively looking for answers for.

[1:18:55] with [1:18:56] sort of qualitative survey data [1:18:58] And, you know, people lie on surveys all the time for a variety of different reasons, but [1:19:03] uh 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 like [1:19:09] what it means to tell the truth and how honest we are with ourselves and with the Internet. [1:19:13] So I really love that book. The other book I really love is... [1:19:17] "Shop would carry water," which is, it's like a parable about a young boy who wants to become a samurai. [1:19:25] But the sort of message of the book is, [1:19:27] about falling in love with the process, especially the most mundane process. [1:19:33] parts of a process of becoming great at something. And that's something I kind of [1:19:37] It's a good... [1:19:39] reminder [1:19:41] about patience, humility, and sort of taking things one step at a time. And I often like reference Chop with Carrie Water a lot. [1:19:47] Reminds me of... [1:19:48] The score takes care of itself, I think is the name of the book. [1:19:51] Yeah, yeah, I've heard of it. With Jim, Bill Walsh. [1:19:54] Amazing. Okay. What's a favorite recent movie or TV show? [1:19:57] Oh, [1:19:58] Man, on Amazon Prime... [1:20:01] I'm a Virgo and it's it's a Boots Riley show Boots Riley directed Sorry to Bother You. It's just blew my mind. You know, so it's super surreal and funny and dark. And it stars Jarell 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. [1:20:23] 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 because it touches on.

[1:20:32] It is a really cheeky way of touching on a lot of really important topics, but often hard to talk about. [1:20:37] topics and themes and it's kind of delightful [1:20:42] to get through it. So I'm a Virgo. [1:20:45] I just binged Barry from season one through four. Harry Winkler was spectacular. And then just came off of Succession, too. The theme here is I like really dark comedies. [1:20:57] Yeah, really, really dark comedies are kind of my thing. [1:21:00] And that first one was called "I Am A Virgo" because I thought you were just saying you're a Virgo. No, no. The name of the song is called "I Am A Virgo." Yeah. Amazing. I will check that out. Okay. [1:21:09] What's a favorite interview question you like to ask candidates? [1:21:12] I think it depends on... [1:21:15] what level [1:21:16] a role that they're interviewing for. [1:21:19] I don't really interview as many like frontline PMs anymore, but I used to really like [1:21:24] doing [1:21:25] case study questions, [1:21:28] And really random ones, too. I'd be like... [1:21:30] Tell me how many people crossed the Longfellow Bridge. Oh, no. And, like... [1:21:35] you know, [1:21:36] a week. [1:21:37] And I could not care less what the actual number they arrived at was, but it's more... [1:21:41] for me to observe, like, what's the array of, like, data points that they can kind of [1:21:46] start to collect in their mind to, to, [1:21:49] inform their calculus and [1:21:51] How... [1:21:53] close can they get to ballpark and like what's their like what's their defense behind their thinking and then you know it's just like the process of watching people's brains move in those moments [1:22:01] is

[1:22:02] You learn a lot about [1:22:04] how they might operate as a product manager, I think, in those scenarios. I try not to overdo them. [1:22:09] So if you think there's a lot of like, [1:22:11] inherent bias in some of those types of questions. And so trying to think of things that are really relatable [1:22:15] to anybody who might be looking to [1:22:18] 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, [1:22:26] If the people that [1:22:28] you most recently worked with [1:22:31] were in a room and you weren't there, how would they talk about you? [1:22:35] One, it's because like [1:22:36] Sometimes I will reach out and get references. And so the extent to which that might actually be part of the [1:22:44] interview process is very legitimate, but also I think [1:22:47] It... [1:22:48] it's usually very clear whether the person is taking like an honest and like introspective, [1:22:53] and self-aware approach to answering that question. And I like to see people being really self-aware because I don't think anybody [1:23:01] 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. [1:23:08] But I try to be self-aware about them. If I can do nothing else, if I can't change them, at least recognize them and do what I can to like, [1:23:15] mitigate the blast radius. [1:23:17] Just getting that. [1:23:19] getting a sense of [1:23:20] 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, [1:23:27] 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. [1:23:32] Do you have a favorite life motto that you come back to or you share with other people?

[1:23:37] The details matter. [1:23:39] And that's both in work and life, I imagine. [1:23:41] Yeah, the details matter. The details matter. And one of the... [1:23:46] I read a cool interview with [1:23:48] the [1:23:49] the product leadership team at Stripe. [1:23:51] And one of the things they talk about is... [1:23:55] for their product managers, [1:23:57] They want you to have taste. And it was a really kind of controversial thing to say because, like, oh, that is so subjective. Like, who gets to decide what taste is? Right. Like that's maybe that's even biased to some extent. And I think they had a super defensible answer. [1:24:10] about how they define taste. [1:24:12] taste in their opinion was [1:24:14] to... [1:24:16] Be so interested in something, doesn't matter what that thing is. [1:24:19] where you can go deep enough [1:24:22] In it, [1:24:23] to have... [1:24:24] a strong set of informed opinions. [1:24:28] Right. [1:24:29] And that's how they defined it. [1:24:31] And they were almost ambivalent to what that thing that was, right? What the subject was. But having taste, I mean, something that you were passionate about, that you have spent enough time learning and understanding. [1:24:42] and appreciating and critiquing and being frustrated with that you have like [1:24:46] a point of view [1:24:48] that is potentially even polarizing [1:24:51] is taste. Like, riding the fence is usually not taste, right? [1:24:55] And so when I think about the details matter, that's almost like a nod to taste, right? Like, [1:25:01] obsess over the details of something, right? [1:25:03] Would that be art, music? [1:25:05] products. [1:25:07] Film, whatever. I care a lot about that.

[1:25:11] I love that and that comes back to a lot of the things we've talked about of talking to customers, looking at the data, like actually having the... [1:25:17] the first-hand information on what people need and what people want from your product. [1:25:22] Yeah, absolutely. [1:25:23] 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? [1:25:29] I fell in love with golf right before the pandemic, but the pandemic really is when I [1:25:35] lost my mind and was like obsessed with golf, right? It was like, you know, one of the [1:25:38] one of the few safe things that you could do [1:25:41] outside that was social, [1:25:43] and less dangerous than, you know, [1:25:45] Getting a drink with your buddy at the bar. [1:25:48] What's the joke? It's like... [1:25:49] I [1:25:50] Men invented golf so they could go on walks with each other. And like, that's essentially what kind of drove the interest in golf. And I'm also horrible at it when I first started. And so, [1:26:00] I think also as you get older... [1:26:02] And maybe you get more... [1:26:05] established in your career, or you know, I've been in a product-led growth [1:26:09] sort of like lame for a while. [1:26:11] you almost forget what it's like to be [1:26:14] really bad at something until you have a kid and then everything's new and you're failing every day. But golf was like, you know, a refreshing [1:26:21] consistent experience of frustration and inadequacy and just like kind of really embracing that and like [1:26:28] just waiting in it for a while, knowing that it's just going to take cycles and time to get better and better. [1:26:33] It was something I got really addicted to. [1:26:35] And so I try to play golf whenever I can. And most recently I bought a Garmin watch. [1:26:40] And that thing is just like magical. Like you roll up to the first tee box, you look at your watch, it knows exactly where you are, which golf course.

[1:26:47] Sometimes it'll even tell you which [1:26:49] you know, [1:26:50] tease you're at because in golf sometimes you're further back and sometimes you're further ahead [1:26:54] And it tracks your swings, it tells you distances. That's insane. It reads the greens for you. Wow. I just want to play golf just to use that watch. [1:27:01] Oh my gosh, if you're... [1:27:03] Some of the guys that I got off with, a couple of them had one recently, and I just was enthralled by it. I literally went home and ordered it that same day, and it's been the coolest thing. [1:27:13] product or gadget that I bought in a while. Damn. [1:27:15] I love it. And I was also thinking as you were talking about getting into golf connects back to your... [1:27:20] relentless curiosity and resilience that you look for in people that you hire. [1:27:24] So clearly you have it yourself. [1:27:26] Final question. I believe you have a dog named Fernie, which is short for Fernette. [1:27:30] Yes, absolutely. [1:27:31] Okay, so on that note, what is your favorite curing cocktail if it's not just a shot of Fernet? [1:27:37] I mean, [1:27:38] The nightcap is always a shot at Fernet. Sometimes you might, you know, mix a little Coca-Cola with that. I think, where do they do that? Is that Spain? I have not heard of that. [1:27:47] Or Argentina, I don't know. It's definitely a country that that's a thing. [1:27:51] My wife has been really into [1:27:53] really high quality margaritas like made at home and [1:27:57] We're big into Aperol Spritz in the summer. So I would say that that's usually what dominates the... [1:28:02] the happy hour rotation these days. [1:28:05] I just had an Aperol Spritz, right? [1:28:09] Yeah, I mean, I'm not good at pronunciation. It's probably one of those two. I just had that for the first time. It's amazing. That's going to be my new go-to. [1:28:15] You had an Aperol Spritz for the first time recently? Yes.

[1:28:20] I don't know what that was. Well, that was like the zeitgeist a couple summers ago. I mean, and then there's the other one too, like the... [1:28:27] Negroni Spagliatos are having a moment to... [1:28:31] It's like a Negroni with a [1:28:33] Prosecco. [1:28:35] Ooh, that sounds amazing. [1:28:37] Yes. 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. [1:28:45] Where can folks find you online if they want to reach out and maybe ask you a question or two? [1:28:49] And two, how can listeners be useful to you? [1:28:52] 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, who works for HubSpot. [1:28:59] I have a Twitter account, I don't spend a ton of time-- oh, X. I have an X account, but I don't spend a lot of time on the app formerly known as the Bird app. [1:29:07] But I'm on Instagram at Millsy Joe Young, which is a nod to one of my favorite old [1:29:13] uh, [1:29:14] Monster Films, Mighty Joe Young. And so, yeah, I'm on Instagram a bunch, too. [1:29:19] That's where you can find me. [1:29:20] And then I know two other things that you wanted to share. One is that [1:29:24] you advise on PLG and things like that. So maybe talk about that real briefly. And then also your hiring [1:29:29] at HubSpot. [1:29:30] Where can people know about that? - I definitely do a bit of angel investing and advising companies on the side. [1:29:36] I really enjoy it. I think there's something really cool and awesome about [1:29:41] getting to see fresh problems all the time and not necessarily [1:29:45] being so... [1:29:46] laser focused on the sort of, [1:29:49] categories or verticals or

[1:29:51] target customers that you're dealing with you know for 40 plus hours a week um and so i i it's kind of refreshing to spend time with founders who are working with products in different categories [1:30:02] having different challenges at different stages of [1:30:05] of growth and being able to figure out how I can be a resource to them. And so, [1:30:09] If you're looking for, if that sounds interesting to you, you're a founder or had a product out there, [1:30:15] Definitely reach out and maybe opportunities for us to collaborate. [1:30:18] And maybe that can be a resource. [1:30:20] Cool. And then on the hiring front, any specific roles you want people to know about that you might be hiring? [1:30:24] There will definitely be more roles opening up in the fall, but I think most immediately I'll be looking for... [1:30:30] like a group product manager to work on the AI platform team that I'm leading. What a role. [1:30:36] Yeah, it's a great role with a fantastic team in a space that might be a little important. [1:30:41] these days and so [1:30:43] 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. [1:30:50] Amazing. Chris, thank you again for being here. [1:30:53] Lenny, pleasure. Thank you for having me. This has been amazing. [1:30:55] Bye, everyone.