Why great AI products are all about the data | Shaun Clowes (CPO at Confluent)

[00:00] I love that you have very strong opinion about this, which is just the state of the product management career and how most PMs are not that great. Why is it that product management is still such a relatively undeveloped discipline? We're like 15 to 20 years into this. And so there's something about the current state of product management that isn't getting at the truly important things, the truly value added things. If we were doctors, you'd be like, that's totally I'd set for it. What's the answer, Sean? How do we solve this problem? Everything always talk from [00:30] a competitive perspective, a very small number of PMs do that. They get dragged into internal politics. They get dragged into scrum management or scrum execution or product delivery. And you just can't win that way. You kind of have this hot take that the way AI will most impact product management is data management. Well, you've got this synthesis machine, which is this LLM thing that's going to help you do synthesis. But if it hasn't got all that data to do synthesis on top of, it's got nothing. And so that means that LLMs can only be as good as the data they are given [01:00] a B2B SaaS app like Salesforce or Atlassian, what happens to these businesses long-term? Do they just become, are they all in trouble? People really underestimate where the value is created in these applications and they just kind of get it completely wrong.

[01:17] Today, my guest is Sean Klaus. Sean is Chief Product Officer at Confluent, [01:21] Previously, he was Chief Product Officer at MuleSoft, which is a billion-dollar business within Salesforce. [01:27] Before that he was chief product officer of Metromile, a public auto insurance technology company, [01:32] And prior to that, he spent six years at Atlassian, where he ran the Jira Agile, and also built the first ever B2B growth team. [01:40] He also created two of the most popular Reforge courses, one on retention and engagement, and one on data for product managers. [01:47] Sean is awesome because he is both very tactical and execution oriented, while also being very philosophical and insightful about the craft of product and growth. [01:58] In our conversation, Sean shares why most PMs are not good, what it takes to become a good or great product manager, how he thinks about his career like a bingo card and why he indexes towards finding very different roles for every new job that he takes, why good data is the most important ingredient in AI tools and for product managers working with AI, also how to build a great B2B growth team, what he's learned about doing B2B growth, how [02:23] and his really interesting take on how AI will and won't disrupt SaaS tools out in the wild. [02:30] If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. [02:39] With that, I bring you Sean Klaus. [02:43] This episode is brought to you by Interpret. Interpret unifies all your customer interactions, from gone calls to Zendesk tickets to Twitter threads to App Store reviews, and makes it available for analysis. It's trusted by leading product orgs like Canva, Notion, Loom, Linear, Monday.com, and Strava to bring the voice of the customer into the product development process, helping you build best-in-class products faster.

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[04:53] Build Better has a 93% subscription retention. Get a personalized demo and use code Lenny for $100 credit if you sign up now at buildbetter.ai slash Lenny. [05:09] Sean, thank you so much for being here and welcome to the podcast. [05:12] Thank you, Lenny. It's really awesome to be here. [05:14] I've had you on my radar for a long time, and I am really excited to finally have you here. And big bonus points for having a very [05:21] beautiful, sultry Australian accent that always helps with the ratings, I think. I don't know if it's causal, but it's correlative. [05:27] I'm glad to be a bit of a curiosity. So I want to start with something I totally believe, and I love that you have very strong opinion about this, which is, [05:38] just the state of the product management [05:41] career and how most PMs are not that great. [05:45] and how there's a big opportunity to level up. Can you just talk about what you've seen there and you're just thinking here? [05:50] Yeah, it's honestly like a big conundrum for me. I think it's actually part of... [05:55] I would say it's grandiose to say so, but a bit of my life's work. Like, why is it that product management is still such a relatively undeveloped discipline? Like we're like 15 to 20 years into this thing, right? You would have thought that it would be less random than it is. Like the outcomes are random, the behaviors are random, individual performance is random, [06:15] you know, seemingly, right? And so there's something about the current state of product management that isn't getting at [06:21] the truly important things, the truly value added things, the right way to think about problems, the right way to think through problems, the abstract reasoning that's needed, there's something that isn't working about it. I've spent a long time trying to put my finger on it and then be like, how do you reproducibly produce that? Reproducibly produce people who can really be really great product managers. The thing is that if you think all the way back to it, like I spend a long time as an engineer and people always talk about 10 times engineers, right? And I wanted to be a 10 times engineer. I'll leave it to others to decide, to tell you whether or not

[06:51] to be, and I tried to be a really great engineer. [06:54] And it must be true that if there's 10 times engineers, and I would argue there definitely are, there must be 10 times product managers too. But at the same time, those 10 times product managers, because product management is ultimately about leverage, so it's about helping other people have dramatically more impact than they would if they were unorganized, if they didn't have somebody to kind of organize the goals and what we're trying to achieve, then that means that a 10 times product manager has 100 times return. [07:18] or more because they're 10 times the return on 10 times resources. So the outcomes are so wild, like wildly distributed, and the benefits are so good that you would have thought that [07:30] I'm not saying that we haven't gotten better, we 100% have. [07:40] But I think we could all say that we're not reliably producing [07:45] 10 times product managers every day of the week. [07:49] I love this point, and it's especially painful that [07:52] When someone works with a PM, that's not great. [07:55] There's just this meme of, why do I need PMs? PMs are useless. [07:59] PMs suck. And it just creates... Like no one's ever like engineers are useless or designers are useless. But there's so many people are like, I don't need product managers on our team. Never hire a PM. [08:09] And it just sets the whole profession back. [08:11] When I first started out in PM, somebody, you know, it's obviously a chestnut, but he pointed out that, like, realistically, when you're a product manager, your job is to say no to 90% of things that get brought your way. And so that kind of makes you the bad person pretty much from the start. And so you're saying no to 90% so you can say yes to 10%.

[08:29] And that kind of puts you behind the eight ball right at the very beginning. And so you have to kind of very quickly get runs on the board. You have to prove to have the right insights, to have the right data, to make the right decisions, or you don't get another go. You don't get another swing at it. So it makes sense that product managers are the easiest to kind of single out and kind of criticize, but that is also what makes it the funnest thing. If you think about, why do we do this? Somebody once asked me, [08:57] would you retire? Why do people do what they do? Because certainly at some point, it isn't just about the money. And at the end of the day, product management is so damn fun because it's about trying to figure out an edge. It's like trying to look at the world, find the portion of the chessboard that isn't occupied, but that is valuable, and find a way to get into it, invade it, and destroy it. It's a really fun... It's decisions under uncertainty, [09:23] And that makes it unbelievably fun, like really, really painful and very frustrating and very hard to convince people, but very, very fun. So, you know, in equal measures. What's the answer, Sean? How do we solve this problem? [09:35] I know you said it's your life's work. What do you find actually helps most in helping PMs level up and become, say, 10x PMs? I think the most important thing, and kind of the chestnut that I repeat to everybody, is... [09:48] is that at the end of the day, the time you spend looking inside the building doesn't really benefit you very much at all, right? And you know, Steve Blanken, people used to talk about you should be spending 80% of your time thinking about things going on outside the building. You might not be outside the building, but you should spend 80% of your time thinking outside the building. And I would say that a very small number of PMs do that. They get dragged into internal politics, they get dragged into scrum management or scrum execution or product delivery, like elements of

[10:18] You just can't win that way. You can never get an A because you're fundamentally not solving the job. The job is not about execution or anything. It's about [10:27] finding reliable differentiated value, right? That you can uniquely deliver into the market. So I would say like, [10:34] If there's one thing, two things I would say actually that I generally guide product managers to do. One is to always start from the point of view outside the building in every document, in everything, always talk from the customer's perspective, from the market's perspective, from the competitor's perspective. And the people who listen to me on that, I would say get better almost immediately because they're starting from a place that's easier to understand. [10:55] And then secondarily, be data informed. They kind of use all of that view of the world, but don't just make up a bunch of statements, like support that statement with, [11:05] You know, anecdotes and bits of data, doesn't have to be a treatise, but like kind of bring in to bring kind of convince everybody of what the world really looks like and what the opportunities ahead of the company looks like. And good things happen to you. And all of a sudden you go from a world where nobody wants to help you get anything done to where everybody wants you to win. They want you to win and they may not give you everything you want, but they certainly will try because they're like, well, of all the bets we could make, this is a good one. [11:30] I imagine many people listening to this are thinking, "Oh, I am that person. I talk to customers all the time. I'm always interacting, looking at research." [11:37] putting data together, [11:39] And what you're saying is you're probably not doing that enough. [11:42] Is there anything that you could help someone recognize of, no, you're actually not doing this enough? [11:48] You think you are, but you're not.

[11:49] It's one thing to say you're spending a lot of time looking outside the building. It's a whole other thing to hear from the places you don't normally hear from. So avoid availability or confirmation bias. Most of the time people go talk to the people they always talk to, and they learn nothing particularly new. They don't synthesize the results that they got from that conversation. They don't seek out the counterfactual. They don't seek out the proof that they're wrong. They don't analyze what their competitors are doing and figure out what that must tell you about the market. [12:19] how their product is actually being used versus how people say it's being used. [12:23] It's like, you know, kind of all data, no analysis, is not very useful. Like, all kind of, you know, everyone can bring back an omnibus edition of, like, you know, random stuff I heard on a Tuesday, but the competitive advantage is extracted in figuring out what other people don't see. [12:41] figuring out where we're wrong, figuring out where a well-placed bet could have dramatically outlandish returns. [12:50] I think firstly, people often say that they do a lot of this stuff, but they actually don't. [12:55] because they don't have any structured way of doing it. So what they really mean is like every now and then I get in a customer call or every now and then I get stuck into an escalation. [13:02] And so they're kind of conveniently bucketing it. So firstly, they don't do it in a very structured way. Then they don't bring back analysis, like a true insights from that thing. [13:10] So they don't really gain very much at all. It's just more activity [13:14] no outcomes. People do far too much activity with not enough outcomes, and there just is enough time in the day to do that, to be successful.

[13:23] You as a product leader is at the Venn Diagram Center of the [13:27] sweet spot of where this podcast has been going recently which is [13:31] product and growth and how ai helps you with all these things and so to follow a thread there [13:39] with [13:39] synthesizing and understanding what people are saying, user research and surveys and all these things. Have you found any tools that you and your team have [13:48] found really useful to help you do this more efficiently versus, you know, traditionally just manually going through all the stuff and finding patterns. [13:55] Yeah, so firstly like stepping back a little bit just into like the motherhood and apple pie portion of like, um, of qualitative research or whatever. Like I find that most people don't even understand [14:05] or don't start with a rigorous foundation in what they're going to need to do to get the answers that they want. So, for example, your listeners have probably heard about the Nielsen number before. But basically, the idea is that once you interview between seven and 14 people, you stop learning new things. Less than seven, you don't learn enough. More than 14, you stop learning anything new. And so if you interview two people, you probably don't have enough data. If you interview 22, you probably had too much. So they don't even right-size their efforts. So that's a problem. So they don't start that way. [14:35] and then we're going to have a [14:36] Asking leading questions. [14:38] which really are designed to get the customer to say what they already want to be true. Which is like, so they haven't done enough research or they've done too much, and then they've blown up all of the results before they've even heard anything. So, you know, if you don't right size your research and you don't kind of set this up to learn, then you're going to lose. Like, no amount of applying LLMs or any type of kind of structured reasoning is going to help you because you're just basically, you're reading back what you want to hear, or some weird summarized version of what you want to hear. But, you know, stepping back from all of that, like,

[15:08] What I like to do, specifically getting to LLMs, is I think that we live in just the most amazing time for product managers right now, in terms of being able to analyze vast quantities of information and see the common threads. [15:23] And so let me give you a few examples of that. One might be you can do a bunch of customer interviews. You can put a bunch of customer [15:31] interviews into ChatGPT and you can say, "Hey, ChatGPT, this is my strategy. [15:36] Tell me where my strategy does not fit what these customers talked about. [15:39] It's all about the not, not where it does, where it does not. Like people spend far too much time looking for what they're hoping to see, not for what they're not looking to see. So you can literally ask ChatGPT to help you find [15:50] way [15:51] the customer's probing at the edges of what you're trying to do, where it's wrong, where what you're saying is not what they believe. And you can ask it questions like that. You can ask it where what your customers are saying would better fit what your competitors are saying. So you can basically say, "Hey, you can copy and paste one of your competitors' positioning documents into ChatDpt and say, "Is this a better fit for what they have said than my thing?" which is you can summarize your own strategy. [16:21] And it's actually surprisingly good at that because mostly your public documents [16:25] actually a summary or at least a derivative of what your strategy is. [16:29] So it will give you crazy insights into what other people's, literally their product strategy, at times creepy, like, "Oh, they will probably do this, "they will probably do that. "It's more likely they would do this than they would do that." And so, like, normally that type of,

[16:42] insight [16:43] was hard one. It took a lot of sweat work. You basically had to read a lot of stuff. You kind of had to use your brain as this big summarization machine. And eventually you knew what you felt about all the things you had read, but you couldn't summarize why. LLMs let you get to that. [16:58] really, really, really quickly in a very structured way, but only if you [17:03] and try to get the answers to what you want to hear. So, you know, I think it's a good question. I think it's a good question. [17:09] you know, prove to yourself that you're wrong, I think is the easiest way to start trying to use some of these tools. [17:15] I love that. And it sounds like in your experience, you're just using straight up open AI, JGBT, Cloud, not like [17:22] Any specific tool for user research for this specific use case? No, mostly I find that the straight up LLMs themselves are good enough. [17:30] And we do have some internal tooling that we built around [17:35] I don't know if you've ever had Sachin Reki on the show. You may have. He was a product leader, pretty well known in the growth community, and he was a leader at LinkedIn for a long time. And he used to call this concept a feedback river. [17:51] And he basically said, "Really smart. [17:53] product managers are constantly swimming in a feedback river. They set out to surround themselves by a feedback river. And I really deeply believe in that. It's like, okay, how can I surround myself with, you know, user interview data, with direct customer feedback, with NPS data, with competitor information? Like I'm always kind of trying to wash myself over with information. And where I'm going with this is that LLMs and tooling based on it can be exceptionally good for this.

[18:19] So for example, we get a ton of, at Confirm, we get a ton of inbound customer requests, as you can imagine, coming from the field or directly from customers. [18:27] We use LLMs to take in those asks, to summarize what they're about, to find other asks that are like that one, like really in a compelling way, like a real way, like a semantic way, not other words that are exactly the same. Are these the same concept? [18:43] So that we can look across all of the inbound demand on us and say, well, the most popular idea is this one and it's getting more popular. The least popular idea is this one. It is getting less popular in a really deep, rich way, even across [18:56] hundreds or thousands of pieces of inbound feedback. I think it's a really great time to be a product manager if you can put these types of tools to work. But they don't do the job for you. [19:06] They just help you do these things that are intricate in that job of finding the gaps, finding the opportunities, finding the common threads, without [19:16] necessarily having to do all of it just inside your wetware, just inside your brain. [19:20] I'm going to stay in this AI river that we're in right now and ask a couple more AI-related questions. [19:26] And this may be what you just said, but I'm curious if there's more here. [19:29] you kind of have this hot take that the way AI will most impact product management is [19:34] is data management and data versus models you're building or anything else. Can you talk about what you've seen there? [19:40] Yeah, I mean, I think there's two implications for people as they're building products based on AI and as they're thinking about like AI in their workflow. So let's start with the first one, because that's how product managers do product management things. You just asked this question of like, should it be specific tools built for, you know, to make AI easier for product managers to use? Or is it in fact like more general models being put to work?

[20:03] At the end of the day... [20:04] These models are very, very, very smart, but they're also insanely dumb. [20:09] Like, and everyone knows that, right? Insanely dumb. In other words, they really only know what they were trained on or what you bring to them right at that moment, like in that millisecond, and then they will forget it immediately. And it's very easy to commit. [20:21] convince yourself that that isn't true, but it's actually what really matters. And let me add one extra piece that makes that really important. At the end of the day, information has a decay rate, [20:30] So think about customer feedback. [20:32] it has a decay rate, or what your competitors are doing has a decay rate. So any new piece of data decays in its value to your decision making very, very quickly. Very, very quickly. You can plot your own decay chart if you want to, but the answer is very, very quickly. And so when you think about the job, which is synthesizing all of this very complicated information to make good decisions, [20:52] What does that mean? [20:53] well, you've got this synthesis machine, which is this LLM thing, that's going to help you do synthesis. But if it hasn't got all that data to do synthesis on top of, it's got nothing. And so that means that, like, LLMs can only be as good as [21:05] the data they are given and how recent that data is. They're ultimately like information shredders. [21:11] They are limitless information eaters. Like they just can't be, you can never have enough information [21:19] to give to an LLM to truly gain its value, the more things you give it, the better it gets. Broadly speaking, that's kind of just not perfect, but that's close enough. And so what that means is as an internal product leader, or putting LLMs to work, you need to figure out how to bring as much information about customers, or their asks, or your competitors, all of it. How can you find all of it and bring it together, and give it to the LLM, either in your tooling, or even in just copying and pasting, or whatever your flow is gonna be, that's one thing.

[21:47] But then if you take it beyond that and you go, okay, well, now I'm a product leader and I'm building an app. [21:52] and I want to put AI in my app, [21:53] What will make my AI experience really great? [21:57] it's definitely not going to be the models because these models are mostly going to be somewhat replaceable and you could say okay well is it going to be the prompts [22:04] Maybe, but certainly good prompts are better than others, and that's kind of an ongoing investment you'd probably want to make to ask better questions, to get the LLM to deliver better answers. [22:14] But it's obvious that the real answer is the context, like all the context you're going to give it, all the data you're going to copy and paste. And so if you think about, let's say I'm building a... [22:24] I have no relationship to this, but let's say I was trying to build a human capital, like a HCM, [22:29] a bot, like an AI bot. Let's say I was working at Workday and I was trying to bring an AI bot. [22:33] it's pretty obvious that the smarts of the bot [22:36] would really be related to all of the employee information [22:39] But not just that, it would be the benefits information. It would be the legal situation in the country where that person is currently working. It would be the company's policies and procedures that apply to it. So you get what I mean by about these kind of like the jumps of logic and the jumps of data and the way data is all linked together. [22:57] If you want to have a smart AI experience, [23:00] you'll convince yourself that all I really need to do is get a model and wire it in, and I'll build a little pipeline that will suck some data in and it will whack it into the LLM. [23:07] And if you think that way, you're going to be very sad, very, very sad for a very long time, because you're constantly going to be wrestling with how do I get data to this thing? How do we get good data to this thing? How do we get timely data to this thing? How do we get well structured data to this thing?

[23:21] And so it's a data management problem. It's getting access to good data, getting access to high quality data, getting access to timely data, and getting it to the LLM to get the LLM to make a smart decision. [23:32] That's where 90% of the calories go. [23:35] Maybe it's a bit like Einstein's thing, you know, it's 10% inspiration, 90% perspiration. Nobody wants to hear it. Everybody wants to just think about what these really cool models and how smart they are, and the next one will be even smarter. [23:45] But really, it's just the hard work of getting really good data to the LLMs to get them to do good things. [23:50] it sounds really obvious as you make this case it makes me think about at the at the lenny friends summit [23:57] Mikey Krieger talked about how he had kind of the two types of PM groups within Anthropic. [24:03] One was focusing on user experience product, and the other was working on the model [24:08] research side. [24:10] And they realized that all of the success came from the model research work, like making the model... [24:15] And the data they provided the model was where all the value came from, not just like optimizing the user experience. And they're just putting more and more of their product team on just that versus like, [24:24] tweaking UX and buttons and things like that. [24:27] Yeah, exactly right. [24:29] Something sort of related. I'm just going to ask one more AI question. I don't want every talk to end up being just all AI. But... [24:35] Something that's kind of been a meme recently, and I know you have a perspective on this, is that AI makes it really easy to build products. So in the future, [24:44] If you can easily clone, say, a B2B SaaS app like Salesforce or Atlassian or [24:49] Whatever your favorite B2B SaaS app, what happens?

[24:53] to these businesses long term? Do they just become, are they all in trouble? They're going to be 100 Salesforce competitors. What's your sense and prediction of what might happen there? Yeah, I think it's really weird. I think people really underestimate [25:07] where the value is created in these applications, and they just kind of get it completely wrong. And I'm not sure why that is. [25:14] So I spent a long time at Atlassian, so I worked a lot on Jira, which many people will know. And I spent a long time at Salesforce, so I spent a lot of time in the CRM ecosystem, the marketing ecosystem, and all the rest of it. If you want it to be not charitable, [25:27] You'd step back and you'd look at all those applications and you'd say they're all just forms on databases. [25:32] You'd say that JIRA is a form on a database. Workday is a form on a database. So Salesforce, they're all forms on databases. Like all vertical SaaS or business SaaS is ultimately forms on databases. [25:42] And you'd be like, well, how hard can that be to replicate? [25:45] And the answer is like unbelievably hard, like unbelievably hard. And people just think you totally get it wrong because it's not actually just about the data model. So if you think about the forms on databases, it's these beautiful user experiences. [25:59] that sit on top of data models, right? So whatever the object is, it might be a customer object or a, you know, a campaign object or some, or an employee object, right? You could say that, well, there's some elements of lock-in in the object, like the object itself, like the fields of the object. I'm like, hmm, pretty boring, right? That's not very interesting, but sure, maybe. Certainly there's some value in being the system of record, like the default that everybody uses. There's definitely some value in the UX, like the, well, you know, I want to be the best, you know, HR-facing applications for working as employee data.

[26:29] there's some value there. But the real thing, which is staring everybody in the face, is it's all about the business rules. [26:34] Like that is what drives the locking. Because like, why do you buy Workday? You don't buy Workday for its out-of-the-box configuration. You buy Workday because you want to configure it to be, you know, Lenny Inc's, [26:47] HR processes, like it becomes Lenny Inc's Workday. It's not, it's not Shawn Inc's Workday, it's Lenny Inc's Workday. And actually, as the longer you have the software, the more it becomes that, the more it becomes less and less like Workday and more and more like your specific company, which makes sense because it was built to be configured to meet the needs of any specific company. And every company is their own precious snowflake. And as that happens, those configuration pieces, that bit that makes the application native and a fit for your organization, makes it a fit for nobody else's organization, and also makes it a [27:17] black box. [27:17] to the point that you don't even understand how it works anymore. [27:20] Like if you went to, for example, Salesforce and you said, hey, could you define all of the processes by which software was sold inside Salesforce? They couldn't tell you that without reading the code of their Salesforce instance. That's not a proprietary secret. That's obviously true. Because over time, that's literally how sales happen. There is no other way to do a sale other than through their internal tooling. [27:41] And so what that means is that it's not the UI that matters. [27:45] And it's not the data model that matters, although those are both very useful. It's the years and years and years [27:52] of evolution of the underlying workflows of the product to support the customers, but also the customers evolving those workflows to make them work the way they do. And so how does that impact AI companies, right?

[28:04] you could say it's easier than ever to build forms on a database application. [28:09] And so I'm like, [28:10] So, you know, you can see that, you know, you can see that, you know, [28:16] probably leads to more power to the existing winning systems of record, because there would just be a gazillion competitors who would just more forms on databases. [28:24] how would you ever choose between them? You may as well just go with the winner. You know, nobody ever gets fired for buying Salesforce or whatever. You may as well start from the kind of the premier vendor. That's one element. You could go the other way and you could say, "I've heard a few people mount this argument. [28:36] which I think is really interesting that at the end of the day, agents are going to take away most of the use of that user interface. [28:44] So let's say, for example, your Salesforce for Service Cloud. I've heard people say, "Well, you know, a lot of those service agents might end up being replaced with agentic workflows. That will mean that, you know, there is no person operating the UI. If the UI doesn't even exist anymore, [28:59] then why do you even need Salesforce? I mean, so we'll just have raw database tables, and who even needs forms of databases? You can literally just have databases. But that also doesn't make any sense either, because the agents have to operate against the rules of the system. [29:12] and the rules are defined by the business processes. So think about Salesforce without a head. Imagine Salesforce had no UI, it would still have those business rules that I was talking about. And those business rules are what define what the agent should do. They're always telling the agent what it should do and how the world can operate, what is possible, what is allowed. [29:29] And so from my perspective, [29:31] like this idea that this just completely destroys like the differentiation of

[29:36] of these kind of business process SaaS applications. This seems like a fantasy, crazy fantasy. The only way I could really believe it is if you said, [29:44] Well, like... [29:45] You could have a new startup that introspected all of the rules that are configured into a Salesforce. [29:50] to try and reverse engineer what your actual business processes are and then kind of operate on top of that. [29:55] But the best place people to do that would be Salesforce themselves. [29:59] or Alassian in Alassian's case or Workday in Workday's case. You know, I just can't see a world in which this, like, [30:06] I think one of two things could happen. [30:09] All this moving to AI makes those applications even better. [30:13] like even more unassailable, like they basically get stronger. It makes the strong stronger, or it could enable some new level of like applications that come from a more platform-based thing, so less a domain-specific thing like, you know, HCM or ERP or, you know, engineering or, you know, less of the domain-specific stuff. It could enable a more platform-like play where you have more business objects [30:43] world in which [30:44] like there's kind of a whole evolution of new, more platform-like SaaS applications that do more than one business function worth of the business rules and the way things move around in the enterprise. But that doesn't exist today. So you could say that that could exist and it could say it could be way better than we've ever thought of because of AI. [31:01] Or you could say that the rich are going to get richer. The most likely outcome is that the currently dominant companies are going to get more dominant.

[31:08] But I don't think this idea that it would just cause a spring up of a whole bunch of new apps that will more easily challenge the incumbents makes any particularly [31:16] It's not straightforward to me how that would happen, basically. [31:18] Wow. [31:19] That was extremely fascinating and there's so much there. I can go in so many directions. One is [31:26] I thought you would actually go in this direction, which is distribution advantages become even more important. [31:31] If it's easy to like today, I could sit there and hire team clone Salesforce might take a while, but I could copy it. But by the time I'm done, they've evolved, they're moving, they're adding features, they're ahead, right? You're skating to where the puck was. [31:45] And so if that's the case, one of the advantages, one of the ways to get [31:49] anywhere is to have some kind of distribution advantage. Like it's one thing to have Salesforce as a product clone another to get anyone to know about it. [31:56] to adopt it, to sell it, procurement, all that stuff. So do you have a sense of distribution advantages being even more valuable in that world? [32:05] Yeah, I mean, it certainly makes sense. Like, ultimately, at the end of the day, distribution is always an advantage, because the hardest problem is to even be in the consideration set. [32:13] for any given problem. The world is full of problems. It's just when people have that problem, they firstly don't think they're going to solve it at all and when they do think of solving it, they don't think of you. So the distribution is always an incredible advantage [32:25] But again, like in the world of AI, it seems like distribution is more likely to get hard than easy. [32:31] So if you think about, for example, diminishing returns on cold email, because cold email is getting easier and easier to send even worse spam,

[32:39] Like it sounds better, but it's effectively causing everybody to become desensitized to everything. You know, I don't know if you've noticed, like half the LinkedIn reach outs now are all basically clearly LLM generated spam. I mean, like to some degree, it's actually worsening the signal to noise ratio. [32:55] And so I think that a lot of the kind of breakthrough distribution mechanisms that startups often use [33:01] seem to be getting more crowded just in general, and more expensive. That doesn't bode well for [33:07] kind of [33:08] I'm not as good Salesforce, but I'm cheaper. It kind of has to be something different. There has to be some [33:16] angle upon which you are materially better, [33:18] And what I saw happening and what I've been seeing happening, I think it's been really interesting. [33:22] is a lot of modern next-gen applications [33:25] and I think that that's pretty compelling, right? So if I give you a look at the next generation of, you know, applicant management products that deal with, you know, inbound job applicants, a lot of them now, like the latest cool ones, they include, you know, your time to fill data. Like, they include outcome data of like, who's got the best hiring outcomes, who, over what period of time has the worst attrition, you know, like literally all the way back to the interviewer. [33:55] and where the interviewers were in the interview cycle. So it basically embeds data into the whole life cycle. And so I think that there are kind of these ways in which [34:06] Startups can bring [34:08] these experience benefits by just bringing a kind of different approach to the world.

[34:12] that does enable them to capitalize on traditional disruptive innovation. Like at the end of the day, this is just disruptive innovation. It means that most companies have overshot their utility, like the average utility, [34:23] So you can win by meeting the average utility and being different. [34:28] meet the baller and be different. Meet the baller and be different is the way to cut through. So that makes sense like that's a half decent playbook. [34:34] But even for those companies, now they're going to have all these AI competitors who are using AI to engineer faster, to build a competitor just like them as quickly as possible and start jamming it into the channel. [34:47] And it's going to be interesting to see how this whole thing evolves. [34:50] you know, kind of got race to the bottom, you know, characteristics around it. You're probably right, the distribution is still [34:57] the hardest part in software, particularly when you're getting started. Right. So if you have some kind of clever [35:02] And fair advantage, it feels like that becomes even more powerful. Say have a platform of an audience or something like that. [35:08] You mentioned this ATS product that you really like. Is there one you want to give some love to you that you think is really cool that you like or you want to keep it anonymous? Yeah, it's Ashby. It's the one all the cool kids are talking about now. And it's funny because people literally talk about it in comparison to even the last generation of modern SaaS ATSs or whatever. And they talk about it in glowing ways because of the way they put data inside the actual workflow.

[35:38] I think that's a pretty compelling user experience. [35:41] So just to maybe close this thread before I move in a different direction, this point you're making about how [35:46] valuable data is and how that's like at the core of being successful and differentiating [35:51] in the future, especially with AI. [35:53] tooling and products any advice you'd give to someone that wants to do that is it just make sure you have a [35:59] Is it like half proprietary data? Is it like make it a first class citizen? Like what's the [36:03] advice you'd give to founders who are trying to do this, what you're suggesting? [36:07] Yeah, I mean, I think at the end of the day, it's kind of all of those things, isn't it? Like if you have first party data, but you can't bring it to bear, then it's not very much use. [36:16] If you have third party data and you bring it to bear in interesting ways, like the problem with data is like we're all surrounded by data all the time. Data is everywhere. What really matters is the right data at the right time in the right place. [36:28] Because we're all humans, right? And so to me, there are obviously data advantages, and there are even data network effects. If you can end up in a situation where you have very valuable first-party data, [36:38] But in any case, it's still about being able to bring the right data at the right place at the right time for those users, for them to be able to get advantage from it. [36:46] You know, like a little kind of segue, I guess, on that one is, um, [36:51] As I said, um... [36:53] I know I spent a lot of my career. Weirdly, I've been a product person for a long time, but weirdly, I've ended up inheriting data teams. I've actually run data teams at a lot of different companies, which is weird because product managers don't normally own data teams. I think it's because I have just a really massive affinity for data. I've always been really data, I used to call myself data-driven.

[37:14] It was kind of my kind of my jam. [37:16] And because I... [37:18] And in hindsight, I look back and I think, [37:20] Thank you. [37:21] data is a data is the opposite [37:24] Data is more like a compass than a GPS. [37:26] If you look at data as a way of giving you the answer, [37:31] You're always wrong. [37:32] You're always wrong or you're slow. [37:34] Wrong or slow or sometimes both. [37:36] Because mostly data doesn't give you the answer. It just tells you if what you just said is like ridiculous and [37:42] or there's potentially something there. So it's more like about disproving whatever you think. And you end up being slow because if you try and use data for everything, your brain is ultimately a data sifter or whatever. So the reason your intuition tells you something is because you've seen a ton of data that tells you that this is the most likely answer. And so being data-driven [38:01] being data [38:03] obsessed is like [38:05] it's something you can easily overdo, very, very easily overdo. So it's about right-sizing data, having the right data at your fingertips, having the right kind of view on data, rather than, you [38:16] kind of like trying to expect data to give you the answer or trying to use data as a weapon or trying to use data as a way to kind of force people to believe you or to go to go in your direction [38:25] But data is kind of at the center of everything and about how to influence and be successful in products you're building and arguments you're mounting internally and everything else. [38:34] I love that you went there. I definitely want to spend time on here. It's interesting you say that. It used to be data-driven. [38:42] like as a Mr. Data-Driven, you created the Reforge course Data for Product Managers,

[38:47] and also retention engagement course and reforge and by the way we'll link to these you're still you're still helping with these courses by the way they're still running they're awesome people love them [38:56] Yeah. Great. [38:57] So we'll point people to those. I love that you're also saying you're like, I think the way you described it to me before this is your reform data driven PM. A lot of people say this. They're like, don't you know, don't just tell don't just do what data tells you to do. Use your intuition, use it as a guide. It's hard, like on the ground and operationalize that advice. [39:15] What's your, say like, you know, to your PMs and your teams when they have, [39:19] data telling them, hey, this experiment is a huge-- [39:23] success or there's a huge onboarding conversion opportunity here. I guess just like [39:28] What's your tactical advice to folks that have data telling them one thing and maybe something else telling them something else? [39:34] I think the first thing I always encourage people to do is to look at a piece of data. If you're looking at a piece of data, [39:40] and the result tells you something that your intuition tells you is like insanely wrong, like probably not right. [39:47] first believe your intuition and go and prove yourself right. Like, don't just take it at first glance because most of the time, [39:55] It's like Occam's razor, the most likely explanation for something that is insanely not intuitive is that it's just wrong. That there's a problem somewhere. Now occasionally, sometimes you actually will be right. Now those will be pay dirt moments. [40:07] Those are the moments that make it all worth it. There are times when you do find the nugget of gold. You're staring at it like, "This is it. This was the problem. This was the thing we were looking for this whole time." But you have to be very diligent about following it through, really understanding what you're looking at. Is this data representative? Is this data a good sample of the audience we care about? Is it already subject to some sort of selection bias? Oftentimes when I see analysis from different product leaders, or even data teams, you're going to be able to do that.

[40:37] can drive a truck through it, literally drive a truck through it. And if you present data [40:43] with authority [40:45] and that data is like ridiculous, or the analysis is just full of holes, you don't just not get benefit for that. Like you lose a whole bunch of browning points. Like it would be better not to show up [40:58] with an analysis that isn't clear, than it would be to show up with an analysis that's dumb. [41:02] And I see people self-immolate on this, actually relatively regularly, because they just bring a knife to a gunfight or whatever. They just bring in an analysis that doesn't hold water, and they present it and then get shot down live, which is nobody's idea of a good time. So if I give you a little bit of additional tactical things about that, it'd be okay. If I'm looking at a piece of data, what was upstream of this piece of data? [41:31] And does that look normal? [41:32] So this thing happened or whatever, which you're very, very excited about. What happened before that? And does that match what you think should have been right? So what happened before this moment's a situation? And then, okay, for that thing that you're looking at, what happened after? [41:45] If you have an idea of what happened before and after, that gives you some idea of whether or not this thing is at all worth interesting to talk about. And then go one click above this data that you're looking at. So it's like, okay, these things, let's say it's... [42:00] I'm looking at onboarding success. Let's say I'm looking at onboarding success to second week retention or something like that. I'm like, I have found this thing that totally crushes it. This intervention crushes it. If you go upstream and you find out that this intervention only applies to 2% of the inbound onboarding stream, it's meaningless. It's most likely just a random aberration. But even if it was not a random aberration, it's not a useful tool.

[42:30] we're even talking about this. Or then you might step all the way back and go, okay, yes, those people do get retained for longer, but their average ASP is smaller. 'Cause what we really care about, we do care about engagement and we care about more customers, but we wanna keep the customers at a high ASP to reach a certain revenue goal. Like the final goal is happy customers paying us money, [42:50] So that's what I mean about going a click up. If you go a click to the left, a click to the right, so before and after, and then a click up, [42:57] and you still see the thing that tells you the story that you want to tell, then now you've got something that's very compelling. Because people want to hear about that. They want to hear, well, what did happen before? What did happen after? And why is that outcome happening? But you have to really do your homework and really be rigorous about it. [43:13] to avoid finding falls gold. [43:15] I love that advice. ASP, what does that stand for, by the way? [43:19] - Oh, average sale price. - Average sale price. - Or MRR or some other, like revenue venture. - Got it. This point you made about how a lot of times experiments show positive and then they end up not being anything. I had the head of growth from Shopify on the podcast and they do this really cool thing where they keep holdouts for years. [43:36] of cohorts. [43:37] And then it auto emails them, I think a year or two later, "Hey, check this and see if [43:42] these cohorts are still [43:44] this is still higher or not, and 40% of the time turns out neutral after a positive experiment long term. [43:50] Interesting. It's really funny because at Adassian, we did something similar. We had a global holdout group, actually, that was held out of all experiments. There was an interview, experiment platform couldn't target that group at all. So 10% of all people never saw anything ever. So that's really, really helpful because you can always compare them against whatever the experience was for any of the same vintage of cohort. I agree with you.

[44:10] But the other thing is I don't really love some of that thinking process just in general. It's like, hey, [44:15] you know, let's say an experiment does show a temporary benefit. If an experiment shows a temporary benefit, but that benefit does not persist forever, you know, [44:22] Does that mean the temporary benefit was never worth it? Or does that just mean the temporary benefit was an opportunity to reach another level? You just didn't capitalize on. I don't think there's a perfect answer is what I'm trying to say. It's like, I do think that the fact that a benefit doesn't last forever [44:35] means that you failed. [44:37] But I agree with you that not trying to understand, well, what has the net benefit been? What has the net lift been? [44:42] It's also really important too. [44:44] That's why growth is so hard. Growth as part of product is so especially hard. [44:49] Marketers, I know that you love TLDRs, so let me get right to the point. Wix Studio gives you everything you need to cater to any client at any scale, all in one place. Here's how your workflow could look: Scale content with dynamic pages and reusable assets effortlessly Fast-track projects with built-in marketing integrations like Meta, C-API, Zapier, Google Ads, and more A/B test landing pages in days, not weeks, with intuitive design tools [45:18] and capture key business events without the hassle of manual setup. Manage all your clients' social media and communications from a unified dashboard, then create, schedule, and post content across all their channels. If you're working on content-rich sites, Wix Studio's no-code CMS lets you build and manage without touching the design. And when you're ready for more, Wix Studio grows with you. Add your own code, create custom integrations with Wix-made APIs, or leverage robust native business solutions. Drive real client growth with Wix Studio. Go to wixstudio.com.

[45:48] you [45:49] So you built [45:51] the first B2B growth team when you're at Atlassian. [45:55] Correct? Yes. Yeah. Yeah. It was, uh, makes me feel like an old person, but yes, it was a very long time ago. Slash it. Maybe, you know, it's a new thing. It's either a long time ago or it's just, we've just recently figured out this is a thing that you could do in a B2B is like, [46:09] Focus on growth. [46:10] Yeah, it is. It's like when I... So it was around about 2012. And at that time, kind of gross hacking was a thing. People don't really use that term anymore. But in B2C, it was a very big deal because people could see Facebook doing their 10 friends in seven days and could see this kind of thing that was working for people. And they're like, man, that's amazing. [46:31] And at UsIn we set out to go, okay, well, do those techniques work in B2B? [46:35] And also, it's kind of obvious now that a lot of them do, and that it's worth doing. [46:40] But at the time it wasn't that obvious because for a lot of B2B companies, I mean, you summarized it earlier, Lenny, distribution covers all faults. [46:48] Like almost all ills can be filled in by really great distribution. Like if you have a really good ground game, [46:54] really good marketing, a really good ground game, and you're kind of jamming your product into the channel, like you're jamming your product in front of people, and you're papering over the ugly parts. [47:02] with [47:02] you know, [47:03] customer success people and services and consulting and whatever, then people will buy almost any software. Or you can certainly be successful with a lot of different software. But back in 2012, it wasn't clear of like, okay, [47:17] Well, if instead you run at this differently,

[47:19] and you've heard them in itself, whether the cell itself, [47:21] Is the juice worth the squeeze? [47:23] And now I would say that it's pretty clear that the juice is worth the squeeze to the point that people, lots of people think about this all the time. But it was a bit of an interesting kind of time at that time. [47:33] And that was essentially the beginnings of product-led growth. Is that a simple way to think about it? No, basically it's now called PLG, but at that time we didn't even know what to call it exactly. Just growth. So kind of based on that experience, a lot of B2B companies now have growth teams that are investing in growth. [47:48] What makes a great growth team in B2B? Any [47:52] any pitfalls you often find folks fall into that you think they should try to avoid. [47:57] Ultimately, a lot of these [47:59] types of endeavors are a matter of balance. So what I mean by that is growth teams tend to go through a set of phases. The first phase is proving their value at all. [48:09] So they call that the gold rush phase. [48:13] That's the, this thing's probably not worth even doing. Why are we doing this? Merry band of people out there trying to prove that there's some growth, growth factor somewhere, right? So that's the proof of phase. And so, you know, the advantage of that phase is like life's good, because there's usually a lot of growth to be found, because nobody's gone looking before. So life's good. But it's pretty random, because you're just literally searching across a random search space going, have we tried X, have we tried Y, have we tried Z?

[48:43] scale this thing? Like, is this just a flash in the pan? You would just find a little bit of, you know, low-hanging fruit and there's nothing else here there. Like, is this just a project we should have done rather than an ongoing thing? So you have to kind of make it a system. Like, you have to prove that it can be repeated. [48:57] And then you have to scale it. It has to become a thing. It has to become part of your DNA. [49:01] you have to be taking a PLG lens to everything you do, all the way from paid acquisition to activation, retention, engagement, cross-product expansion, upsells, I mean, you name it, like all the different ways you can grow a product by revenue or engagement. There's many different ways to go about that, and so you end up having to scale out and be able to do all of those different things. [49:21] And then you have to figure out how you fit in with the rest of the organization, because there's other people who build products all day, every day. There's other people who sell that product all day, all day. There's other people who market that product all day, all day. And so, you know, growth organizations [49:35] are in this interesting space, they're in between everybody else. They're kind of in everybody else's sandpit in a little way, and they're kind of at the edge of everybody's full-time job. And they are very valuable, but they can be complicated because of all those relationships, and because of the way they sit amongst all of the other parts of the organization. [49:54] So many organizations fail because they don't really find much that wins, or when they do find wins, it just seems totally random, or they do find a lot of wins. [50:01] but they all can't understand them because they seem like they're just a random walk through a bunch of potential opportunities. There's many different ways to [50:10] can fail to fit as you go through your growth phase from trying the ideas to success, to scaling, to operationalizing.

[50:18] One of the biggest memes along these lines is... [50:20] A lot of companies... [50:22] claim, just PLG rarely ever works. [50:26] You always... [50:27] event, either you try it and it just doesn't work or it eventually just peters out. I guess [50:32] Any thoughts on just like what are signs that your product [50:36] has a chance to work [50:38] He'll... [50:38] product-led growth versus you just go straight to sales immediately and don't even worry about this. [50:44] First, let's examine the counterfactual, right? So let's start with the opposite of your question and say, hey, [50:49] you know, how would the world be sadder if we all just gave up on PLG? Like if we just said, "Hey, there's no point in doing it in B2B SaaS." [50:56] The problem is that there is not [50:59] a natural force that pulls [51:04] companies [51:05] towards thinking about [51:07] the end users [51:36] if you don't think about that end user. But it's one thing to say that you should think about the end user. It's a whole other thing to have a system by which you do that. [51:45] Because people pay lip service to all sorts of things. But, you know, I'm sure you've heard this one before, but in economics, like, people only do what their incentives tell them to do. Like, broadly speaking, that is what they do. That is what happens. You get what you set out to measure. You get what you give people incentives to do. If there is nobody in the organization whose true incentive

[52:03] is to measure that success, the end user success, their enjoyment, their happiness, their retention, their engagement early on, it will not happen. [52:10] Or at best, it would be a hobby. [52:13] And so then by extension, if I start from there, then I say, okay, let's say it doesn't exist. [52:18] PLG doesn't exist and therefore it's a hobby and therefore there will be a bunch of hobby people who care about this, then you ask yourself, okay, will that mean that there will be many products for which those experiences really suck? And does that mean that that will be an opportunity for competitors of those products to be better at that? And is that a differentiated competitive advantage? Yeah, I'd say it is. I'd say it is. And so I just work my way backwards and I go, okay, you can say that your PLG investment might be too high. [52:48] like this is not, like I can't spend my life just experimenting in the onboarding. That's not the only thing that matters. And that's very, very true. But it's very hard to argue it should return to zero. [52:59] And so to me, therefore, it's about the balance. It's about, okay, how does PLG fit [53:03] with the other different ways that I grow in my business. So at Comfort, for example, we have a PLG function. We do grow with self-serve signups, people who sign up, literally their credit card, like lots of them sign up and they're very successful, never speak to us. We also have like an enterprise sales team that sells directly to very big companies, some of the biggest banks in the world, people you would definitely know of. I don't think it has to be one or the other. I think that it's about a balance. It's about getting the motions to work.

[53:33] companies, the people who really know this, [53:36] It's about making both motions work together. [53:38] Like if you can get a PLG motion work to feed your sales team, and a sales team motion work to feed your PLG funnel when the sales leads aren't ready yet, [53:47] and you can get those emotions into playing with each other, you can make a lot of money. It can be an extremely successful way to go, to build a very resilient business. Why? Because you get a lot of customers, [53:58] and you get a lot of revenue. [53:59] You can't be that successful as a company if you have a lot of revenue but a small number of customers because you're captive. Everyone knows that. You can't be that successful as a company if you have a lot of customers but not enough revenue because you just don't have enough money to sustain operations. So the magic is in having both a very large number of customers and a very large amount of revenue. It's very hard to knock over a company like that. [54:19] If I look back on my time at ASEAN, [54:22] And I think that they shared their most recent numbers. I can't remember what it was, but it was in the public. [54:26] data or whatever, 80,000 or 100,000 customers, something like that. That's a lot of customers. That's a lot of customers. Let's say you're going up against JIRA and you're like, "Yeah, [54:37] I'm going to pick off a thousand customers. [54:39] from Adassian. That's a lot, right? That's a lot. Obviously, a thousand customers is a lot. [54:44] you only have 19, sorry it's going to be like [54:48] I can't remember their exact number of customers, but it's very hard to assail a company that's not a good thing. [54:58] which has a very large number of customers and a very large amount of revenue. [55:01] And so that's why I think that POG as a mechanism is incredibly important

[55:07] for almost any type of company, if you can make the motion work. Like obviously there are companies for whom the motion just is irrelevant. [55:13] But for those where it does matter, [55:15] It seems like the juice is worth the squeeze. [55:18] That was an awesome answer. I looked up last thing, they have 300,000 customers. Oh, man, I'm so far off. When I left, I must have 80,000 customers. They've done good work since then. Also, you're talking about incentives and how the power of incentives. Charlie Munger has this great quote I looked up just to make sure I get it right. [55:37] Show me the incentive and I will show you the outcome. [55:39] Yeah, exactly right. Exactly right. You know, I've seen I've seen like cases where like a sales team was a [55:46] people trying to get a sales team to do like a P or G motion, [55:50] And you can beat them over the head as much as you like. You can get into a meeting and tell them that you really, really want them to do this. But at the end of the day, they're not going to do it. And the same is true for every other kind of function. It's just the nature of things. I have some newsletter posts around the stuff if folks want to dig deeper. Also, Elena Verna had an awesome podcast episode talking about product-led sales and kind of the combination of these two things that we'll point to. There's like a whole other topic we can go deep, deep on, but we're not going to do that in this episode. [56:17] Maybe just one more question. [56:19] So you mentioned all of the companies you worked at. So you've been at Salesforce, G-Product Officer, MuleSoft specifically within Salesforce, Metromile, Blasian, Confluent now. [56:32] a lot of really interesting and different roles. [56:35] How do you choose where to go work? [56:37] and how do you choose which opportunities to take? I imagine you have many options.

[56:41] I like to think of my career in hindsight looking at it this way, Lenny, so like I'm just, I don't know, forward looking it was obvious to me this way, but looking back, my career's been a little bit like a bingo card. [56:52] Like, I've always been looking for... [56:55] to fill in boxes I didn't. [56:57] have failed. [56:58] because I felt like that would make me a better professional. It's like if I didn't know anything about that specific type of sales model or that type of marketing or that type of, [57:08] product management or that type of product or that layer in the stack or that kind of thing, is if I learn about that thing, I will become more versatile. [57:16] So actually two things. It's fun to learn something new. It's fun to prove to yourself that you can do those new things. [57:22] And then it makes you more versatile because it means that any given problem you go up against, you've seen something that pattern matches to it. [57:30] It kind of feels like you end up bringing it down to a knife fight in a way, because every problem you look at, you're like, oh, I haven't seen this from the other side. Like I've seen this from some other angle. And so I know that this is likely to work and this is unlikely to work. [57:42] And so, you know, when I joined, you know, early around in my career, I was working for a big enterprise software company, sorry, small enterprise software company that sold to the Fortune 100. Then I joined Atlassian, and like I shared with you, [57:54] We had no Salesforce at all, actually, at all. Literally nobody sold itself or didn't get sold at all. [58:00] and we grew to have 80,000 customers. Like it was just pure product, they had growth, and just an incredible company. [58:06] Then I was at Metro Mile, which was a consumer company, that got acquired, made an insurance product for end consumers.

[58:13] got nothing to do with technology products, like literally a complicated [58:18] Internet of Things device you installed in your car, but ultimately it's an insurance product you'd sell to grandmothers in Florida. [58:24] as much as you would urban millennials. And then we also have to totally back-end software that's used by IT organizations and a consulate. [58:32] you know, infrastructure that's used by developers everywhere to build really interesting data-driven applications, data-powered applications to do all sorts of things in real time. [58:40] And you look across all that and you go, it's all a bit random, right? [58:44] But I didn't see it that way because I actually was in sales for a bit. So I ran a pre-sales engineering group, went around the world selling software. So when I joined the last end, I wanted to kind of understand what it was to sell software at massive scale. [58:58] with no sales team? Can it even be done? And so I learned a lot in my time at Atlassian [59:03] When I went to Metro Mile, I'm like, well, I've never built a consumer product before. [59:07] Like I can say that I've actually built a product that's touched many millions of people, because Jira has, so I felt pretty good about that. But I'd never built one that I could say, "Yep, [59:13] A consumer, your average consumer can use this thing. It's so simple, even my grandma can use it. I'd never built a product like that. [59:19] So I got that experience at Metro, which is really fun. [59:22] I'd never worked inside an organization as big as Salesforce. [59:25] or an organization with as good a sales motion. You talked about distribution earlier. [59:30] Salesforce is an absolutely insane distribution machine, just an incredible company. [59:35] within just an amazing distribution network, and a fantastic marketing approach that, like, [59:42] It's like a PhD in marketing. You know, when you spend your time at Salesforce, you're like, "This company is just one of a kind." It's a one of kind, and it's so outlandishly good at one specific thing. And so looking back, you know, all of these jobs,

[59:55] have been, when I say a bingo card, like I've just got an outlandish education [1:00:00] in these areas that [1:00:01] are not obvious at all. And once you've seen them, [1:00:05] they're like superpowers, they're superpowers to be able to bring that, to bring that same experience to bear on things. [1:00:10] And so one thing that I really... [1:00:12] I'm trying to figure out this way. Often people don't do that. [1:00:15] And oftentimes people stay in a very specific domain, like they prefer to stay in a domain, or they prefer to stay in a specific kind of type of company or a role that works in a certain way, like companies that have the same operating [1:00:30] model or they plan the same way or they try to stay with [1:00:34] things that are pretty similar. [1:00:35] But it seems obvious that the most likely way to kind of really grow is the opposite. It's to constantly be choosing things that are outside that, not totally outside the lines. Like don't jump out of a plane if you've never parachuted before. Obviously you want them to be in some way an adjacency, [1:00:53] that you want them to have something in common with what you know, but you want them to stretch you and change you. [1:00:58] You know, I... [1:01:00] I had a really transformative experience [1:01:03] many, many years ago when I was at Atlassian, and a guy called Tom Kennedy, he was our general counsel, so like chief legal officer, basically, and a lifelong lawyer, very smart guy. I liked him very, very much, but like just a lawyer, just a lawyer, you know, corporate lawyer, corporate counsel. I'm sure you know what they're like, and really great guy. And I remember, so mostly in our meetings, like our meetings, he didn't talk that much except about legal things, right? But I

[1:01:33] about a product strategy question about what we should do. Should we go left or should we go right? And like as usual, he's there and he's mostly just staying silent. And eventually the conversation has been going on for 15 minutes and he's like, hey, everybody, [1:01:47] Like a year ago, we talked about X, Y, and Z, and he proceeds to lay out our product strategy at that time. And he's like... [1:01:53] Just recently, we said the following things, and that was a product strategy, whatever. Now, you're saying this. Isn't it obvious that that isn't this? Like, what you guys are saying is not congruent with that. And if you really meant what you said back then, we should be doing X. [1:02:04] And then like the room went silent. [1:02:06] Everybody kind of turned to him. [1:02:09] kind of nodded. [1:02:10] And then everyone went, "Yeah, okay, I guess we probably should be doing it differently." And so the meeting stopped when the GC randomly mentioned that he deeply understood our product strategy and he knew enough [1:02:21] to be able to contribute in that way. And so the life-changing part for me about that was just this realization that, [1:02:29] If I'm going to be a really great professional, [1:02:31] If I'm the type of professional I want to be is that type of person, the type of person who can contribute to the whole company in all sorts of ways, like doesn't spend all of their time in everybody else's business. [1:02:42] but understands the business and has the mental horsepower and the experience [1:02:48] to be dangerous, [1:02:49] in all sorts of, and I mean that in a compliment way, I don't mean that in a negative way, but to be dangerous in all sorts of situations. I think that when you have kind of like leaders like that behind you and with you, [1:02:58] then you're just unstoppable. You're an unstoppable force in business when you kind of have that motion happening.

[1:03:05] Wow, that was an awesome story and an awesome story. [1:03:09] perspective. It's similar to the advice I always give PMs of [1:03:14] People are always wondering, should I go deep on a specific subject? Should I just... [1:03:18] try different things and I find just variety especially early in career is really [1:03:22] powerful, not just to help you discover the thing you like, but also to your point, just [1:03:27] using insights from all these different parts of the product and, [1:03:30] like internal tools and trust and safety and platform and [1:03:34] consumer product side and growth and just core stuff. [1:03:38] Like the more that you have, the stronger you get. [1:03:41] And I feel like another benefit of your approach is if you work at just B2B SaaS companies, you're never going to, like if you have too many of that on your resume, [1:03:49] It's very hard to get hired a consumer company [1:03:51] And so just having creates a huge optionality for you if you do what you did. [1:03:57] Yeah, it's interesting because people used to talk about people who are T-shaped or whatever. [1:04:02] I've never really loved the analogy. [1:04:05] because it's more like people are scribble-shaped. [1:04:08] Like, I mean, like, they're the really best people you've worked with. They're more like scribbles than they are T-shaped because, of course, you want to be horizontally capable. So you want to be broad. [1:04:17] and you do want to be deep, [1:04:19] you actually want to be deep in way more than one thing now obviously when i say deep i don't mean like [1:04:24] Like, I'm not... [1:04:25] able to do the job of like, you know, our finance function all day, every day. [1:04:29] But I'm 100% good enough to go like... [1:04:32] three clicks below, like the simple financial analysis. Like I can go reasonably deep in our financials,

[1:04:38] because I want to and because it's partly like it matters. Like it's important to be able to do that. And so maybe a different way to think about that bingo card is like, [1:04:46] I've really regretted [1:04:48] going deep in something that isn't quite my job. Like I've really regretted it. Like the worst case scenario is I've learned something new that I will never use. [1:04:56] which I guess at least that made my brain slightly more agile. I don't know, there must be some potential benefit of that. But the very best case scenario [1:05:04] is that when I least suspect it, [1:05:06] at some point in the future, it will turn out to be the thing that matters. Like, it will be the tool that I need. [1:05:11] but I'm facing some important problem. [1:05:13] And I will be like, oh my god, this is worth every cent. And so if you think about it on an ROI basis, [1:05:18] doing things that aren't in your wheelhouse, like that aren't the things directly in front of you, [1:05:22] The ROI can really be outlandish. It can be off the charts great, but I guess it's speculative because you don't know you're going to need it tomorrow. You don't know if it's going to be something that's going to be a regular tool to use. [1:05:33] It's interesting you use the bingo card as the analogy. What happened? Are you trying to... [1:05:36] Is there a bingo moment at the end of this? Is there retirement? [1:05:40] Is there... Oh, you mean like you've got everything? You've got collectible of Pokemon? [1:05:46] Yeah, I was working with somebody at Salesforce and he was like a really, he'd been there a long time, very, very, very successful person, like honestly, didn't need to work anymore. [1:06:01] And he said something that I found really useful. He's like, well, now I'm at the point in my life [1:06:05] where I want to work at the intersection of things that I am good at,

[1:06:09] and things that will be valuable to the company to do. So basically, it feels like the reward of completing a bingo card is actually to just get to spend more time [1:06:18] doing things that are leverage, that you enjoy and that are high leverage. And so that seems like a good outcome to me. [1:06:24] It's not as though you're going to [1:06:26] I don't think most people are going to work and hopefully have some sort of great financial outcome, and then go, "Well, that's it. I'm picking up stumps. I'm retiring." I think for most people, achieving some sort of financial outcome or some sort of [1:06:39] you know, [1:06:41] independence or whatever is really just another stage. It'll be, at that point, it will be, okay, well now what do I do? Like, what do I do with my life? Like, why, [1:06:49] And so that was what I said earlier, that at the end of the day, [1:06:53] Product management is at times the worst job in the world. [1:06:58] and at times, easily the best. [1:07:00] and it's both, and it can be both. And so, you know, it's hard for me to think about what, you know, if I think about the things that are the intersection of what I'm good at and are valuable to the world, product management is a pretty fun one to do, and it's different every day. So I think we're pretty privileged, for those of you who listen, I mean, obviously your podcast reaches a lot of product people, like I think we're pretty privileged to be able to operate at that intersection. [1:07:24] But it's not easy because [1:07:26] you know, you gotta show value. You know, it's like, it's not, it's a very complicated job to show value in and to demonstrate value to the world and to, uh, [1:07:34] It's constantly being attacked, like you mentioned, but it's still amazing. Like when it all goes right, you know, when a product is very successful in the market, it's hard to describe the joy you get from that.

[1:07:45] Kind of along those lines, to close out our conversation before a very exciting lightning round. [1:07:50] I want to take us to Failure Corner. [1:07:53] People listen to these podcast episodes and everyone's always just sharing all these wins. Everything's always going great. The CPO of this, CPO of that, just moving on up. [1:08:02] And people would want to hear times of things that didn't go right because those are stories [1:08:07] People don't share as often. [1:08:09] Can you share a story when something didn't go right, when you maybe had a failure in the course of your career? And if you learned something from that? [1:08:16] experience what you learned. [1:08:17] I mean, there's a lot of things that didn't go exactly to plan, Lenny, like very early on in my career. [1:08:24] I was a developer and I accidentally deleted one of the core systems of the company that I was working at. So that's going to go down in infamy, but luckily that one's far in the rearview mirror. That wasn't Atlassian? [1:08:40] No, no, no, that was far pre-Elasian, but very bad. Yeah, you know, the one I like to talk about, I wasn't directly responsible for it, but I feel like responsible for it. I was at a company and we launched a product [1:08:53] that was one of those products that, you know, in hindsight, should have been really obvious it was going to fail. [1:08:59] But for some reason, we were all blinded by the potential. [1:09:04] It was a product that was basically to measure the environmental impact of your company and to help you reduce the environmental impact of your company by doing-- think about it as, like, power management, building power management, managing the power drawer of computers, managing the power drawer of, you know, AC and all of that stuff. That was the vision, basically. It's like a kind of a manage your environmental impact of your business.

[1:09:28] And the idea was pretty cool at the time. And also, it was the right time for that. And it's still a thing. It's still an area of active research and investment or whatever. [1:09:37] But it was one of those things, [1:09:39] Talk about the wrong company. [1:09:41] wrong place, wrong time, wrong distribution. We had literally no [1:09:45] right to win, no right to play, like just absolutely no business in hindsight being in that business. [1:09:51] And I feel really bad because, again, good idea, wrong company. And at the end of the day, we launched the product. [1:09:59] We actually kept the product in market for two years. [1:10:02] And the final straw was weird. The final straw was actually when a customer finally wanted to pay for it. [1:10:09] It had been a market for two years, and we found ourselves with a customer who wanted to pay millions of dollars for it. They were ready to sign on the dotted line. [1:10:16] And that was actually the moment we decided to kill the product, because really, if anybody, if this person signs this piece of paper, we are stuck with this forever. Like this one customer will be bound by contracts for however long or whatever. So we actually ended up killing it at the moment, after two years of failure, when kind of somebody wanted to pay his money for it. And I look back on that and I'm just like, [1:10:38] man, that was a really big, I feel really bad because it should have been obvious, it was obvious, and we should have been able to call a spade a spade and speak truth to power. But instead it kind of got through to the keeper and turned out to be a real accidental drain on resources for years and just a big mistake.

[1:10:58] So there's a lesson there. [1:11:00] Just be real with yourself. I like that you have this forcing function of like, "Okay, let's get for real now." I wish we had an earlier forcing function to force us to make a decision. [1:11:11] Yeah, I think if I could do it differently, I might not have necessarily been able to 100% change the decision, but I should have tried. [1:11:20] Like, I mean, it was pretty obvious after six months. Like, this thing was a bit of a zombie product, walking. [1:11:26] And it would, you know, it would, the least I could have done is said like this thing is dead. Like we could have called it dead way earlier. But instead we proceeded for another year and a half investing in it. And so that's the bit that makes me kind of feel like a real bummer about it. [1:11:39] It reminds me of a recent episode of the Raws. [1:11:41] who is the CMO at Wiz. [1:11:44] And she joined us the first PM and a few weeks into it with doing tons of calls with customers. She's like, I think I need to quit because I don't really understand what we're building. I don't get it. [1:11:55] And everyone's like, [1:11:57] You know, like I don't I don't either. [1:11:59] The founders just had a vague idea what they were doing, but they didn't really have an [1:12:06] And that just sparked the, okay, wait, no one actually does. Let's actually get more concrete. And it helped them pivot and now... [1:12:14] I don't know if you know about Wiz, but they ended up being the fastest growing startup in history. [1:12:18] "You see, isn't that amazing?" Right? It doesn't mean it's permanently fatal, but asking that question and going through that [1:12:26] Reckoning turned out they came out stronger.

[1:12:29] Scary, but it turns out it's for the best often. Before we get to a very exciting lightning round, is there anything else that you want to mention or leave listeners with, maybe a last nugget? [1:12:39] something that you think might be helpful before we... [1:12:42] Raph. [1:12:42] maybe a couple of different things that I think, sometimes well understood, but just repeating them, I guess, because they're very valuable to me. One is that if you let your calendar rule you, then nothing good will happen. [1:12:56] I know people talk about that a lot, but it's surprisingly common in product management, in particular, that people end up ruled by their calendar. And so it's related to that whole, "I'd look at it, spend 80% of your time thinking about things going on outside the business." [1:13:08] Easy said, very hard to do. [1:13:09] And if you don't do it, no one's going to do it for you. And so it's really hard to be successful unless you find a way to force that to happen. And so I'll repeat that. [1:13:17] I kind of also like somebody said this to me, and I never actually looked up the quote. [1:13:22] But apparently Colin Powell said, [1:13:24] that if you're making a decision with less than 30% of the available data, [1:13:30] you're making a big mistake. [1:13:31] If you're making a decision only after you have 70%, it was either 70% or 77%, I can't remember the exact number. When you have 77% of all the available data, you have waited far too long. [1:13:41] And I've always found that very insightful and it relates a little bit to what we were talking about about data earlier. But at the end of the day, we get paid in product management to make decisions, good decisions, paid to make good decisions that will deliver business benefit. And a decision with too little data is fatal. A decision that takes too long and collects too much data is also fatal. So like everything, it's about trying to find the balance of all of these different things to try and deliver business advantage.

[1:14:08] A great way to circle back to all the things we've been talking about. With that, we've reached our very exciting lightning round. Are you ready? Yes, let's do it. [1:14:17] Let's do it. [1:14:18] What are two or three books that you have recommended most to other people? [1:14:23] Yeah, the oldies but goodies is probably going to be the main startup that I still find actually really good. And the kind of key lessons in there, I still think are very applicable to a lot of people, particularly the cohort analysis bit, which for some reason I still don't see people do anywhere near enough cohort analysis. So there you go. That's my little tip. And then Inspired, how to build products that people love by Marty Kagan and the Silicon Valley product group. That's an oldie but a goodie. I think, you know, it's got a lot of the key lessons of product management in it, even though. [1:14:52] It's been a long time. [1:14:53] Those are some classics. Very cool. Do you have a favorite recent movie or TV show you really enjoyed? [1:14:58] I'm watching a program, like, just to, I don't get to watch very much TV. Mostly at night, I like to watch things that are extremely light. [1:15:06] that just don't at all [1:15:09] I think it's called Detroiters. I think it's a great thing. I think it's a great thing. It's a great thing. I think it's a great thing. It's a great thing. [1:15:18] I've been watching that. [1:15:20] Yeah, it's really funny. I really like that. It's so ridiculous, but very funny. So I like that. That main guy, he's so funny. I forget his name, Tim Sweeney or something like that. Yeah, he's so good. The Heralds, yeah. Good one. I've been watching that and loving it. It's like very quirky. I think the New York Times quote on there is like very weird. It's so weird. Like in the first episode, I'm like, what is this show? It's not even clear what time it's set in. And like, it's very weird. It's really cool. Yes. Well, good way to describe it. Next question. Do you have a favorite product you recently discovered that you really love?

[1:15:50] - Yeah, this one, some of your listeners might be using it, but Glean, it's a pretty well-known startup now. They recently raised a ton of money. We've been using Glean at Confluent for a long time, and it's just, [1:16:04] I'm like, it's just amazing. I can't describe how good it is. And I don't say this lightly because I think search, like a business search is probably one of the hardest problems in computing. Actually, getting it right is one of the hardest problems in computing. Amazing. It's not often I use a product and I'm like, this thing is like 10 times better than anything that's come before it. [1:16:23] It's one of those for me. [1:16:25] What's the simplest way to understand what it does for you? [1:16:27] Thank you. [1:16:28] It searches all of our organization's knowledge. [1:16:30] So the thing you were just saying before, you're like, you know, what does ASP me? [1:16:36] If I had that in a meeting, I just opened my new tab, it'll automatically take over my new tab. I'll just be like, "What does ASP mean?" and it will summarize back to me what ASP means, and it will give me a link to all the documents inside our company that just grab what ASP means, and then it will tell me who the expert in ASP at our company is. [1:16:53] It's like having a second brain. [1:16:55] It's like an insanely cool kind of organization search thing. [1:16:59] Great tip. Okay, two more questions. Do you have a favorite life motto that you come back to share with folks find useful and work in life? [1:17:06] I think about this one a lot. You know, when I started off in my career, I was a, you know, an engineer's engineer. I used to very much about like technical correctness and what computers were capable of and kind of [1:17:19] technical righteousness, you know, the right answer rather than, you know, there is only one right answer and whatever. It's a long-winded way of saying that I often think about this phrase, which is, um, people don't care what you know until they know that you care.

[1:17:32] And so I've realized that really being able to influence people, it doesn't matter about whether or not you're right or whether or not you're wrong. [1:17:39] And at the end of the day, it's first about trust and about relationships. [1:17:43] and caring about what each other's outcomes are, what their incentives are, and all good things sit on top of that. [1:17:48] Once you have those kind of foundations, then you can build like really good partnerships. And that's where good progress comes from. [1:17:55] Wow, that is so good. [1:17:57] It connects with like radical candor, similar, like in theory of just caring. They need people need to feel like you care deeply about them before they. [1:18:05] Take your advice. [1:18:06] And it also connects with this parenting book I'm reading called Listen. [1:18:09] that a previous guest recommended, which is all about [1:18:12] how your kids... [1:18:14] have problems when they feel like your connection to them is weak. And so the solution is to build a stronger connection for them to know that you care deeply about them. So this is really, [1:18:24] Connects with so much of what I've been reading. [1:18:25] Great one. [1:18:27] Final question, you were born in Sydney, folks, you may be guessed by your accent. [1:18:33] If someone were to visit Sydney, any tips, anything you think they should check out, favorite thing in Sydney? [1:18:37] Yeah, Sydney's a really beautiful city and like it's kind of famous for its beaches and it's a basically a metropolitan city. People will probably be very surprised when you visit it. It's a very big city. [1:18:47] very metropolitan, a little bit like New York, but New York was really beautiful beaches. If you want to think about it that way, it's kind of crazy. But there's actually like a ton of really cool nature and beautiful things all around Sydney. And so if you want to do something like off the beaten path,

[1:19:02] You can actually go to, there's an area called the Blue Mountains, which is like an hour and a half drive from Sydney, and you can have sail down a waterfall. [1:19:10] which is, well actually firstly you go canyoning through a canyon full of water, and then you have sail of waterfall at the end. And if you're looking for like just a really beautiful, fun kind of adventure like thing, an hour and a bit away from a massive metropolitan city, [1:19:26] That's my sort of happy place, like really beautiful outdoors stuff while also next to a beautiful city. [1:19:31] And you said you sail, what sort of sail off a waterfall? Abseil. You might think of it as repelling, I think. Oh, okay. Yeah, lowering yourself down on a rope. Got it. Okay, because when I hear sail, I'm like thinking a boat just jumps through over the waterfall. Oh, no, no, no, abseiling, which is also, I think in the States, you guys call it repelling. Repelling, yeah, wow. Yeah. Very cool. [1:19:54] Sean, you're awesome. This was extremely cool. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out? Also, point folks to your Reforge courses that... [1:20:02] you created and final question, how can listeners be useful to you? [1:20:07] Sure, yeah. So my Reforge courses, you can check them all out at reforge.com. As you mentioned, the retention engagement course and the data from product managers course. So, you know, love to see folks get some value from that. Lots of people have been through those courses already and [1:20:21] I really get a lot of value from it because like I said, one of my goals is to like, [1:20:25] help all of us be better product people. I think our leverage could be massive. Where you can get in touch with me, obviously LinkedIn, but also Sean M. Klaus on X, if you want to get in touch. And in terms of being useful to me, I mean, broadly speaking, I'm always open to new ideas. Like if people have ideas about how to do better, B2B,

[1:20:45] P or G, better B2B product-led sales, for example, better ways of going about distribution and product-led sales and product-led growth inside enterprise companies. Hey, I'm open to learn myself. We're all in one big journey learning how to do this better. [1:21:01] So true. Sean, thank you so much for being here. [1:21:04] Awesome. Thank you very much, Lenny. It was great. [1:21:07] Bye, everyone.