Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)

23:14And so you want to get the balance of those two things. So when I think about rippling, I think of you guys, kind of the cultures to do things the hard way and the right way. And an element of that is there's this concept that I've heard that rippling is this compound startup. What does that term mean? And then how does that approach impact the way you build products in organized teams and all the things you were just talking about of MEPs and you know, build new products? The idea of a compound startup for us is that we're basically a lot of businesses that all work together. Right? Like if you think about about the products we offer, we have payroll.

23:52Well, there's entire companies built just on payroll, insurance and benefits, entire companies, that's an entire life. In fact, like a fragment of benefits is the entire life cycle of the whole company. You know, our IT products device management and identity management, time and attendance, each of these things are industries into themselves with like multi -billion dollar companies serving each of them. The insight Parker had before he founded the company was like, actually the result you get that when you have that is that there's all this data that gets replicated and copied as impossible to keep in sync everywhere.

24:24The right answers to have a single system of record, one place, one database where all of that information is resident so that each of these downstream systems can always have the right data at the right time and then you can build on top of that, you know, things like workflow and reporting and analytics and permissioning and all these kind of underlying capabilities. So the idea of a compound startup is like all of these different businesses benefit from being built on top of one platform. The activation energy for that is extremely high. Right? So before my dime at the company, you know, Parker, Prasana, the technical founder and others, you know, built all of the first versions of all of these products and it was a minor miracle that they were able to do that.

25:05But having done it, right, we then had that platform and we could continue to build like new verticals and new startups, right, on top of that foundation. This touches on something that comes up a number of times on this podcast, which is the importance of differentiation. And it feels like this is the differentiator for rippling. It's not going to be just a better one of these vertical solutions that the main differentiators we're going to do it all and everything's going to be so much better because it's all in one platform. Is that kind of where the original idea came from? Is there a different way to think about that?

25:37Yeah, I think that's right. So I mean, the fundamental contention is having a single system of record is better for many, many, many reasons, right, the most simple of which is there's a single source of truth and like all of these other products can rely on it. But also, unless you start without assumption of everything being in a single system of record, there's a bunch of other things you can't do, right? You can't you can't build out a, I don't know, a permissioning system that looks at the various attributes across all of these products. You now suddenly have to do an integration and each of these products talks different languages.

26:10You can't do simple things like build a product and say, who is this person's manager? Most products you can't do that. Most products you find some system of truth, export everybody's name and email address in a spreadsheet, you know, have another email address or another name, maybe an employee ID of like who that person reports to and upload that to another system, which by the way is immediately out of date because organizational structures change all the time. Whereas it's rippling, it's always correct, right? We are the system of record. So all of our products, they're like, hey, who's that person's manager and the system immediately knows, right?

26:45And that's a very, very simple example of something that that you can only do if you start with like solving to come back for earlier point, like solve the most complex use case first, right? Solve the fact that this data all needs to be in the same place. And so our ability to kind of differentiate, right, boils down to kind of that one fundamental decision, which just allows us to do things that are literally impossible for any other company to do. What would you say is one of the most unique things about rippling culture that maybe you haven't mentioned yet? I would say it's fun, a speed of execution, right?

27:18I think in speed of decision making, it's the thing that is probably the hardest to explain to people before they're here, like it's hard to understand until you experience it. Like, let's not schedule a meeting for next week or tomorrow or later today. We're in the middle of a meeting. We need to make a decision. Let's either make the decision or if we can't, let's like slap call in the person that we need in order to make that decision. And we'll be done with the decision today. And like sure, there are irreversible decisions who can't make that way, right? But for the most part, we really value like the tempo of decision making and the speed of response.

27:54And no company I've been at in any scale, five people, five thousand people has ever operated at the tempo of this one does. And I think that our ability to continue to operate at that tempo, which is partly due to the fact that we are a compound startup and have these small independently operating teams and all the rest of that is a really differentiating thing about the culture of the company. I'm reading Kevin Kelly's new book, or I don't know if you've seen his new book, it's all these little tidbits of advice. And one of that usually the best time to do something is right now. And it feels like that resonates with the way you all think.

28:29I'm curious just how you create that culture and ability to make decisions fast. Does it purely top down founder? This is how they behave? Or is there something else that you found is effective to create this culture of moving fast making decisions really quickly? Obviously a huge piece of this is like Parker himself, right? It's an attribute of his personality, likes making decisions quickly. And it's also a deliberate strategic decision on his part to have a company that makes decisions quickly. And so he models this constantly, right? In Slack, in conversations, in person, in every way possible.

29:01And there's an expectation, kind of throughout the company, if you kind of look at our leadership principles, like this ability to make decisions quickly is something that kind of everybody promulgates. But also, I think there's a number of things we've done to sort of bake it in, right? Like in the way that we even do like say quarterly planning and the fact that like there's this timeline for decision making that doesn't leave like, you know, a lot of room in the way that we expect people to know their domains, especially in product, right? And product your, you don't own like feature, you own like your product and your expected to be the world's foremost expert in it.

29:36And if you are, what that means is like instead of having to come back to people three days later with an answer just off the top of your head, you can be like, yes, this is what I think I should do about that. Or you know, give me 30 minutes, looks up the up. And like I can tell you what we need to do about that. And so all of those things in combination just yield an environment in which these decisions happen very quickly. You talked about quarterly planning and you're saying that there's like, here's the timelines. We need to make decisions on these dates. And there's a culture of just we stay firm to that.

30:03And if you don't, then we're going to move on. That's right. And so, and so it's it's shocking to people when we actually move on, right? That haven't been here yet. It's like, no, no, that date passed. You know, you know, it gets to like retroactively like like make everybody react to the fact that you didn't operate quickly enough. Right? And it's and it's not a it's not a hostile thing. Right? It's just a people just have to get used to it. So it's a it's a deep cultural principle. And the fact that everyone stands behind it, uh, it just means it's like gets reinforced on that sort of its own out of its own gravity.

30:34Do you have values like internal values? Do you kind of outline that are a part of this? Or is that not something that you find super valuable? No, we actually I find them quite valuable. And actually our CEO Matt McInnes who, you know, joined the company about a year before I did, you know, he has been the one to like really drive this. And you know, you go to, I can't remember this specific URL. But on rippling, there's a search for rippling leadership principles. You know, there they are. And they are really true to the culture of the company. The way we came up with them is was to us, you know, a couple of years ago to introspect and to what the what actually made people successful at the company.

31:08Like who's successful? Why are they successful? Why do they enjoy being here? Or alternatively the opposite? Right? Like why people not worked out? Why do some people like not enjoy here? And like those are the things that are differentiating and of those of the things that we wrote down. Are you hiring or on the flip side are you looking for a new opportunity? Well, either way, check out Lenny's jobs dot com slash talent. If you're a hiring manager, you can sign up and get access to hundreds of hand -curated people who are open to new opportunities. Thousands of people apply to join this collective and I personally review and accept just about 10 % of them.

31:45You won't find a better place to hire product managers and growth leaders. Join almost a hundred other companies who are actively hiring through this collective. And if you're looking around for a new opportunity actively or passively, join the collective. It's free. You can be anonymous and you can even hide yourself from specific companies. You can also leave anytime and you'll only hear from companies that you want to hear from. Check out Lenny's jobs dot com slash talent. For someone listening, that's like we need to move faster and everyone always feels this. We need to move faster. We make decisions faster.

32:21What what piece of advice would you give someone for helping them do this at their company? I think it's really context dependent, but I think it starts with, you know, whoever is in the role of making the top level product decisions, of them being one extremely clear about what those parties are and more importantly, extremely clear about what all the parties aren't. There are so many things that could be important or people can make the case for being important or whatever that are fundamentally distracting from the core mission of getting something done. But secondly, for that person to go all the way to ground on it, we have one of the leadership principles is go and see.

33:02Right? So to look at the thing and then walk all the way to ground and talk with the engineer who's writing the code on the thing because inevitably, this top level communication is insufficient to get to the detail of what matters and doesn't matter. You don't have to do that everywhere, but if you do it in enough places, what it does is it creates a clear expectation of that kind of clarity across the board and forces everyone to up their game a little bit and just helps people understand what the expectation is. Right? I think in the absence of those sort of clear expectations, it's difficult for people to like perform at their best.

33:41So we try to do that pretty frequently. Okay, I definitely want to spend more time on this, but before we get there, so go and see, I love that. And that actually has come up recently on a number of podcasts. Just the importance of people continuing to ask questions and going to like the of what's possible. Recent story was IO talking about building the cash card and going like the warehouse and watching the printing of the cards and things like that. Yeah. I guess first of all, you have a sense of where that came from and why that ended up being so important to you all. And then two is just, is there an example of you doing that or someone you've seen do that and that leading to something really important?

34:16In the early days of our kind of global efforts, right? When we are first trying to figure out what global payroll was, it was really tempting to say, like, oh, well, we're going to go into the UK and that's going to be like relatively similar to what we're doing in the US. But our kind of head of payroll went in and said, like, actually, here are the ways in which like we know it was going to be different, but here are the ways in which we didn't anticipate that it was going to be different, which made us realize that we had to completely alter our approach, right, for how we think about learning about each of these countries and going into them and having like a full sum experience and then backs into things like, well, every country does tax filings.

34:55Every country does them slightly differently, but how are we going to build a tax filing system that's going to allow us to like satisfy the needs of every country in which we're going to run payroll, right? And it was only through that like very early on, like deep look at how one country was actually operating and then doing the same thing with the next country that like we were able to set in motion all of those things, right? It's not only we knew all the answers at that point, but it allowed us at a much earlier stage to put in motion a bunch of stuff that we need to do that then got subsequently much more clarified and much more precise than over time.

35:30And so the the leader that team basically just went and studied the tax laws to be kept country. That's right. Like when all the way to ground, it's like, okay, like let's go and open up the big ol' like it's like online these days with the old tax book and like it's like, or in the United States, like you have to go look at Ohio or Pennsylvania which have all these like little like local like city or county based taxes. And it's and it's incredibly instructive to look at just a few of those and think like, wow, how do I think about like configuring these change like unannounced, right? Like some city administrator, you know, or the city legislature would have like all them right.

36:08They decide to change the tax rate. Well, how are we going to know about that? How are we going to change it? How are we going to change it? So it's effective at the right time. And you don't think about those things until you've gone all the way to ground and looked at how these things are actually worked, how they're communicated, how they're thought through. And I think the same thing is true of every aspect of every product, you know, in different ways, right? It might be a technical thing, it might be a design thing, it might be a compliance or regulatory or governmental thing, but whatever it is, that detail always exists.

36:35And then unless you're getting down there and seeing and understanding it firsthand, you don't really understand what your product needs to do. And I think an important element of this that's between the lines, maybe is don't delegate this to someone like you may have a tax expert on the team. And I imagine many leaders would be like, go go figure this out and tell me. And I think what you're saying is you go do that and learn, become the world access right. That's right. That's right. You go do it. You go learn. And then we can make the case for hiring the tax expert, right? Which we do have by the way, now, right?

37:03Like, that's that's an incredibly important part of our success is having that specialist, but not before somebody with a product mindset, like the tax specialist is amazing at tax, right? That's but that doesn't make them necessarily a great product thinker, right? So the person with the product thing has to has to get into those same weeds first to really understand it. Do you give any guidance and just like how much time to spend on all that stuff versus like, you know, the regular day to day of say a product leader on a team, you know, there's it takes a lot of time to become a world expert on the tax systems of many countries.

37:36Or is it just like there's nothing more important than that? That is like your job. And what are you doing not doing that? How do you think about that? I think it's an equilibrium, you know, if a job is 80 hours a week, it's like 40 of your hours. Like it's I think I think that that you can't really understand a product unless you've gone there, right? And yes, it takes time. And you're right, you can't just ignore like the other half of the job of communicating with, you know, the engineering team and like writing documents or whatever, but like what's the point of writing a document if you don't know what you're talking about?

38:06Right. And so, and so we very deeply value that. And it's one of the reasons that we keep, at least at rippling, our product organization, really thin, right? We expect like a single leader right to be able to know like the full scope of product. In fact, great product leaders can in fact do that because they like have this native curiosity and interest and like ability to absorb a lot of stuff. And it makes it's a lot of fun because now like I have a group of people around me who like are all like really good at what they do and really understand what they do. And that that's kind of just an amazing, amazing place to be.

38:42I'm looking at this list and I just want to keep asking questions about it. One of the certain principles that I love is, it reminds me of Amazon, has the same principle I believe, which is leaders are right a lot. Yeah. Why do you find that to be important? I know you weren't necessarily designing all these principles, but I imagine that something that you guys follow often and comes up a lot. I mean, this is one of my favorite ones because I think for, particularly for a product or right because product leaders have to be right most of the time because their decisions reflect across the entire org and that their decisions fundamentally spend time, right?

39:18And they spend energy. And if they make good ones, the company does really well. And if they make bad ones, the company doesn't. And one of the things I really value in product leaders are people who can go into like an ambiguous information with ambiguous situation with incomplete information and then like a complex decision space and can like look at that and listen to everybody and read whatever they need to read and say, this is where we need to go. And like even if everyone else is like, I don't know, that feels wrong for this reason, this reason, if they have like the confidence to like make that call.

39:51And then a year later when you look back on it for them to have been right, that's extremely valuable. And it's one of these things that like it's really hard to test for, right? You can get it by like talking with people and asking, hey, it was this person like usually right and respect people think about it. But like in the context of like a given company, just you have to take the time and see if those decisions are largely right. And it's the one value we have. It's like, you can't really learn it, right? Either you're really, really good at making those kinds of decisions or you're not, right?

40:25And it's a very peculiar skill that we really value. Awesome. Shifting a little bit. I know you all are going through this global expansion. We talked about this a little bit. And so just a few questions along the lines because a lot of companies start one country, most companies too. And then they decide, let's expand to new markets. So I guess first question is just how do you decide which markets to go after and specifically where to start first and then just prioritizing the list of markets? What's so it starts with the assumption that we're going to have to be everywhere ultimately, right?

40:59That you don't actually have to build like native global payroll in every country in the world. It makes sense to that every country in the world. But you definitely want to be able to pay people in any country in the world and you want to be able to have contractors anywhere in the world and have their information be in your HRIS anywhere in the world. And so the decision for us, we were fortunate to or when we made that decision to have quite a few customers, already like thousand thousand customers. And so we knew not only where their kind of US employees were, but by virtue of being an employee system, we actually knew where they had other employees.

41:29And so it was quite easy for us to say focusing on US based companies, which is incomplete data, right? But if we just look at our US based companies, we know that there is immediate demand for those people to pay people in your country's X, Y and C. And we just like listed those out in wrong numerical order. And then we kind of looked at, okay, how hard is it to build in these countries and how valuable is it to build in these countries? Right? Like what is the strategic value of building in the UK or Canada or Germany or India or wherever? And then we had a discussion on like where's their risk?

42:01Right? Where where is this? Where's this hard? Where's there a long pull? Where does this like in what countries does it take like a long time to get approval or whatever? And we just stacked ranked them. And and then we revisited that decision, right? Like the early decisions that we made on exactly which countries like we have subsequently like re -ordered those over time. And as we've dived into countries and learned more, we, we we we we we we we we rejigger things like a little bit. But for the most part, like that same basically as we started with is still like, you know, mostly right? Okay, and then the other question a lot of founders always struggle with as when is it time to start expanding internationally because you know there's pros and cons.

42:36Do you have a sense of what convinced you all to start going international? I think our case is slightly special, But I think the right answer to that question is always before you think you do. Before you think you need to. Because like, it's harder than everyone. If they've never done it before, it's harder than you think it is. It's more specialized than you think it is. People in the UK really, really care if there is a you in color. Just as we care if there's not a you in color, right? There's like all of these subtle lessons that like cultural lessons for companies that take like a really, really long time to absorb.

43:08And so my view is you always should do it earlier than you think you should, than you think you have to. In our case, it was always something we knew we had to do. In fact, we have a very clear thesis that companies that aren't global, particularly in payroll, but also in kind of insurance and benefits and IT. If you're not global, you're just not going to be around in 10 years. Because companies were becoming global. And then COVID happened. And companies became global much faster, right? It stopped being the province of like 100 person companies plus and like started filtering down into very, very small companies.

43:42Just became commonplace for small companies to be multi -country. And so that very much accelerated kind of our time table. And then you saw, you know, other people noticed that too. And you saw other companies starting to try to address parts of its problem as well. And so there's this kind of competitive dimension, which is sort of secondary in most ways, because we were going to do it anyway. But like that also kind of adds a little bit of a, you know, fire under the, under the thing. What have you found to be most surprising about expanding internationally to be successful in, in expansion for folks that are maybe starting down the road of like, oh shoot, we should think about that.

44:16I think the thing that was most surprising to me the first time I did this back at Godwire in the, in the OTS. And remains the most surprising thing to most people, you know, every time I do this again, is that every country is unique. You can't just like, you can't just take your US -based approach and like drop it into another country. Other countries find it insulting. It doesn't matter how much success you've had here. Everyone always believes rightly or wrongly that their local context is special. And you have to respect that. And it comes down to like little things like they're being a you and color or not.

44:52Or, you know, if you ever see a demo delivered to somebody in another country, where they see like a detailed screen about a person at an includes a social security number, it's like they immediately lose credibility. It doesn't matter how good all the rest of your stuff is. And so that is consistently the thing that I think is most surprising to people is the degree to which that's true, which seems obvious in retrospect, right? If you took like German system or something and like demoed it in the United States with like poorly translated stuff, we would think it would suck too. Right? And so, but it's not, it's really hard to adapt to that mindset.

45:26And so it takes just a lot of energy to kind of overcome that organizationally. Makes tons of sense. I'm going to go in a different direction now. Frameworks. So I know that you're not a huge fan of frameworks. We were chatting about this before we started recording. And so curious just to hear your perspective on why you're maybe not a fan of frameworks. And then also just like how you crystallize processes and concepts for your team, if you're not just like here, here's a framework you should use. Look, I think frameworks are very helpful. So I'm not exactly anti -framework, but I am anti -process as a substitution for deep product thinking.

46:04Right? So I like to have just enough process to create a frame. Right? So the right decisions can happen and like no more. And I think there's a danger, especially as company scale, that you end up saying, well, you know, if only we categorize, you know, everything correctly and Jira, like, you know, we will be able to make like really good prioritization decisions. So I'm like, sure, extremely helpful to have clear categorization and things in Jira's and have like data and analysis and to be able to do all of that stuff. What you really need to do is decide what's important to build, right? And then like have a way to build it like really efficiently.

46:38And so I think the right answer, the right amount of process for any given team is like or the right framework for any games is really just dependent on like their specific life cycle. So you won't see me saying like, oh, we need to use like this scrum thing or that combo thing or whatever like the latest newest thing is, it's like, don't care about any of that. What I care is about something that's going to enable this team in this context, at this point in their life cycle, to build the right thing as efficiently as possible. And I'm fine if those are different for different teams. And the only place I care about Unification is one of the quarterly planning process and two, like, everything does need in fact to be in Jira because otherwise you can't rationalize about what's actually getting done and not.

47:18Is there a processor framework that you find is like counterproductive that you're just like stay away from this thing? We've had a lot of trouble with it or generally it's like, let's just rethink everything ourselves. No, I don't find one to be particular. I don't, I haven't consistently found one to be particularly problematic. So I think any framework sort of has this place, you know, right place, right time. I think there's, I think there's danger any one time somebody like dogmatically says, I think we should use process X because that's almost never the right answer in my, in my experience.

47:48I think, I think there are places where that can differ. Like you start a company like on the basis of process X and like everyone's bought into that process and everyone understands it. I mean, they can be really, really great. And like, and on the engineering side, I think this is hugely valuable. It's like test -driven development. First line of code is going to be a test. Not the actual thing like fantastic, very supportive of all that. But I think it's kind of different in the product world. If you had to compare the way Coinbase builds product process wise or just product development process wise to Ripling, what would you say are the bigger differences?

48:17I think the differences are largely born of like the different domains, right? So crypto, as we talked about earlier, really hard to predict what's going on. There's all these questions about what's the future of crypto, what's going to matter, like what do we even need to build, what's going to survive. And so the process we had a coinbase around like having those debates and like getting to a decision and disagreeing and committing. And then from an execution point of view, being able to move fast, like that was the trick, right? At Coinbase. Here, we know the things that we need to build, like at a high level.

48:47And the trick is how do we really differentiate it on the basis of like these amazing platform capabilities we have or how do we have to evolve those platform capabilities in order to continue to build something that's just continuously better than everything that's out there. And that like yields a different decision making process. So for me, it's like the mental model is actually of how I approach those things with the same, but they just like yield different results in the in the actual making of the software. What is that actual difference you find like day to day? Is it like timeline differences?

49:17Is it how quickly, I don't know, the way structure, how far out you plan, what do you find is like the concrete difference as a result? I think the difference is in the day to day velocity of like decision making, right? Because we can you know, rippling if you're like on, I don't know, to go around the team, if you're on the device management team, like you know what you got to do, right? There's no ambiguity. You're not debating about, you know, whether, you know, Mac or Windows is going to exist in the future. Like none of there's none of that cognitive dissonance, right? There is, we need to build this.

49:52It's hard to figure out how we need to build this, right? Because there's all these different things that we could leverage, but we need to basically get this done. And so the the kind of total velocity, I would say, is is higher here, which does not say people work harder or less hard. Columbia is like, Columbia is like an amazingly fast like environment, but it was also subject to the fact that like you just don't know what the crypto markets are going to do and you have to be incredibly reactive to that. And so I think maybe that's the one thing like the the reactivity to like the environment, the crypto environment, what's going on and the uncertainty of the regulatory environment, all of this, if we are really, really, really good at handling those things really rapidly, which is something that we need to handle somewhat less here.

50:33It sounds quite stressful. Yeah, I mean, it was, it was fun. Like I stress, yes, it was stressful. I mean, every job I've ever had has been stressful, but in in its own unique way, but all of that stress, I think, is in the shape of a problem that's in the context of a problem that's really interesting. I mean, right. And so, but yeah, it's stressful. I'm looking back. What a joy. Yeah, they are very good memories. Like I look back. I don't really, I remember the stress, but I don't like re -experience it. Right. I remember like, you know, forging these relationships and building these amazing products that that I've been so lucky to be a part of.

51:15And so I have, you know, almost only good memories of the places I've been. That's what I find too. You go through these hard trips. And then you look back and you're like, wow, that was so cool. But assuming they go well, assuming the company works out and like it feels like, you know, it was successful. A lot of times you're to start up your life sucks for two years and it doesn't work out. And that there is a lot of, you know, upside and good memories to that, but it's less, less glorious. Yeah, that's fair. Though, I mean, the first company I was really at kind of out of school is company -led reactivity back in internet one era.

51:50And we were trying to figure out like, how does this internet thing work out? We start companies on the basis of these technology. How do we help other companies like build stuff and figure it out? You know, in that company, like fundamentally, like didn't work out. Ultimately, God kind of spun itself out and got acquired, which, which was great. But like, it was this extraordinary set of people that I was so lucky to work with. And I, you know, I loved all the time I spent there. And it was foundational to like everything else I ever did. And so even though that effort didn't like, you know, pay off in the traditional set, like the value of the the learnings I had there.

52:24And then the people I had a chance to work with was just really exceptional. So, it's still very lucky. That's a really good point, actually. And I think I should correct even what I said, that even when things don't like work out traditionally, those experiences end up being incredibly valuable in all these unexpected ways. Yeah, 100%. Yeah. Okay. So, final topic. I want to talk about hiring, hiring product managers and interviewing. Yeah. So you've hired a lot of PMs over the years. I'm curious what something you've learned about what to look for in product managers and also just in product leaders that other people may not be focused on as, you know, I mean, I don't know that I have any like particularly special insight here.

53:04I, I think there's a couple things that I do ask that that maybe are more of an emphasis because it's rippling than than not. But like the first of those is when people are going through our process as a part where they they do this case study. And an important part of the case study is that it's like actually too complex for people to like have all of the answers up front. It's just like the space of the problem is too large to do that, which means that like in the interview, there's a lot of opportunities or in the case of there's a lot of opportunities. So just like ask ad hoc questions or to like change one assumption.

53:35And seeing how people react to that is really indicative of how deeply they understand, you know, a new problem or how quickly or how mentally agile they are. And you know, some people are extremely good at that like here in assumption and they like blink a couple of times. So like, oh, well, that has like these 400 implications, right? They just start rattling the ball. And some people get like really flummox, right? I mean, obviously for our environment, that former is like really, really important to us. I think the other thing that really matters to me is like the insightfulness of questions that people ask, which is indicative of number one, their like actual interest in the job, right?

54:14Like people tend to ask better questions when they're like more excited about working at a place and like done their research and are asking people about it. And also like the quality of those questions like can vary quite dramatically. And that's okay. I don't expect to call you the same all time, but like sometimes people ask questions like, oh man, I would have never thought to ask that question. That's such an insightful question. And then I pause. I have to think about my answer a little bit. And so kind of usually a pretty good candidate on my hands. Is there an example of someone asking a really good question like that that comes to mind that you think back to you and like, oh well, that was great.

54:48I remember about three years ago, I was interviewing a guy named Kyle Boston. And Kyle is now, now runs our platform product organization. And I can't remember the specific question he has, but it had something to do with, wait a minute, if you have all these products and you have this like employee system of record thing underneath it, shouldn't we be thinking about like how to create these like various pillars of kind of underlying platform technology things like like permissioning else. And this was before we like fully formalized the concept of our like platform beyond the kind of employee system of record.

55:29And I remember thinking like, yes, yes, we should. And you know, that had entered our minds before, but the fact that somebody which who had like almost no context on the company, right, that that's what was impressive about this question. It's like, man, you've been thinking about rippling for like a couple weeks while you're like interviewing other bunch of other companies or whatever. And like you've thought about it deeply enough to have this insight into the nature of the platform that we're building, like immediately, like gave me a bunch of confidence in his ability to kind of think through the sorts of things we need in the think through.

55:58And I think it touches on PMs need to be business leaders. And yeah, great questions are often about the business and the future of the business and how to make it run more efficiently. And this and you know, there's like a product org element to it. But I find that that's like a really under appreciate element of PM and he's just like thinking about the bigger business, not just like the PM product. Yeah, for me, it's like two things. It's like thinking about the bigger business and having having the context like around, you know, whether it's like revenue questions or strategy questions, but also like the detailed questions, right?

56:29It's like, oh, wait a minute, the implication of this thing that I'm getting asked or of this thing, Jeremy that you said earlier is all of these things, right? And their ability to kind of understand that that this isn't a simple business. Like it's really hard. It's really complex and the ability to kind of to have these insights help them think through those details is really cool. You talked about this prompt. They you give product managers not to give away what you actually asked these days, but is there an example of a prompt that you've given in the past or you think is like a good example of a type of prompt to give a product manager candidate?

57:01In terms of like a general kind of approach, I think a prompt should always like reflect the actual business that they're going to kind of come into, right? So when we do like so our process overall is actually quite short. It's basically, you know, getting contact with us somehow eventually get you know connected with a hiring manager, have a conversation with them, then more or less you have a conversation with me, which is a product discussion and then we have a case study, which follows that that's the whole process, you know, modular of other conversations around the edges. And the questions that matter are around like how do people think through that product discussion, right?

57:38Which is relevant to our business, how do people think through that case study? That's number one. And the second thing is there's always a part of my interview, which is, which is maybe sounds very simple, but it's just like, hey, what questions do you have for me? Right? We actually do that before we do the product discussion. And that's an incredibly important question because it is again indicative of like these things that people have thought through or not thought through or kind of the depth that they're thinking or their interest and engagement in the role. And like at that second discussion, it doesn't have to be like perfect or anything.

58:13But it is a very strong signal when people, you know, whether they thought through a set of questions they want to ask or just like, you know, on the fly, like generating them, you learn a lot about how people think about product about, you know, what they're looking for, about, you know, what they like doing and not doing just through those questions. For pms that are maybe in their early career that are listening to this, what advice would you give them to help them accelerate in advance their career most in their early part of their career? Be humble. Being a product person means that like by definition, you're living in a world where like no one knows the right answer yet because if somebody did, they would have already built it.

58:53Right? And so having like no matter how smart you are, there's less smart people out there. Right? There's always stuff you don't know. There's always people who are going to know things that you don't know. And it is only through that acknowledgement, right? That you can actually have the humility to say, like, I'm open to absorbing all of this stuff. I don't know. And open to synthesizing all the stuff and coming to different conclusions. And so I found that that humility is one of like the biggest differentiators in early career product leaders who sort of are, you know, able to let go of like how awesome they were in school or in their first job or whatever.

59:25I mean, I had to do this. And like and realize like the job is always hard. And the job is always about discovery every single day. And if you can maintain that like curiosity and elasticity of thought and creativity and like, like solutions, it could be awesome. But if you close yourself off to that and think you always have the right answer, then there's like no hope. As touches on another principle that I still have sitting on my screen here, which is great leaders change their minds a lot or just change their minds. Yeah. willing to look at new information and say my mental model is adjusted by that or I was wrong very simply.

1:00:03I mean, I think it's also important to be operating in an environment where you're allowed to say that you're wrong. Right. Everyone's wrong sometimes. I mean, be right a lot, but everyone's wrong sometimes. Right. And and being able to be in environment where you can just like say, yep, I was wrong. Here's the way in which I was wrong. Let's move on. Isn't credibly powerful. Final question. You've brought up Parker a number of times and something that is clear about him is that he's a very product -minded founder.

1:00:29He's a founder like that is often a challenging place to be similar to being the first PM at a startup and the founder has strong opinions about product. So my question is just what have you learned about being successful as a product leader with a founder that is very strong opinions about with a production team? Yeah. No, it's a great it's a great question. So I think you've got to be adaptable. Right. Like it's like any other relationship, right? You have to understand like what the nature of that relationship is where that person's going to care, where you're going to care the ways in which you can challenge each other.

1:01:04Like I think fundamentally you need to make sure that person is willing to be challenged. Right. So you know, I've seen product leaders or CEOs who are like kind of unwilling to be challenged. And I wouldn't be able to work with those people. But but yeah, Parker is incredibly strongly opinionated, but he's also incredibly informed, which makes for some really, really great debates. And I've just found that like whatever, as I even see you, but whatever a manager's idiosyncrasies are, you have to find a way to like work with those. And I think that that adaptability like I'm just sort of I like being like, you know, a moldable puzzle piece where I can just kind of fit in.

1:01:41I think that's actually one of my one of my core skills. So and so that's worked that's worked out for me. And I know Parker and I before I started, you know, started developing like a deep foundation of respect, which is like extremely important to like building that. And like over the years, it's just gotten deeper and deeper. And you know, we don't always agree. But like when we don't, we can have a totally reasonable discussion about it. And and you know, that's what makes it fun. Adaptability actually is I took a strength finder test once of finding my own strengths. And that was my number one strength is I'm a developer.

1:02:14I think we share that. That's excellent. Yeah. Seems like an important attribute for being in a place you're in. Well, with that, we've reached our very exciting lightning round. I have got just requirements for you if you're all right. I'm ready. Hit me. What are two or three books they recommended most to other people? Well, first is like my favorite series of books ever, which is the Baroque cycle by Neil Stevenson. It's a nine volume epic or three three volume nine book epic, depending how you want to look at it. But like it's about the time like just before and like into the enlightenment historical fiction, a lot of fun.

1:02:48And I also love the culture series by Ian Banks, which is just like super fun, far future sort of a universe that I really enjoyed. What's a favorite recent movie or TV show? Watch the last of us. You know, it was an avid fan of the game. And I thought they did a really really nice adaptation. Favorite movie. Like I guess recent movies, not that recent, but I really like Tenet, which which I thought was a I'm I was impressed with their ability to kind of go there and make that movie. And I just really enjoyed it like end to end. We had a it's kind of ended, but we had a drinking game anytime. So when mentioned last of us, which took over white Lotus, I'm going to drink some tea right here.

1:03:29Okay, Faradah, I'll try I've only got water normally I got tea, but water good at works. But it's interesting and hasn't come up often. So I think maybe we end that for now and see what the new pattern. And then Tenet feels like I was just thinking it feels like a compound movie. Compound started up as a movie. That movie is very complicated to. Yeah, I enjoyed it. I like I like to like figure out like the multi -timeline chart in my head as the movie progressed. The puzzle piece within you trying to find all the puzzle pieces. Yeah, for sure. What is a favorite interview question like to ask you already maybe answer this, but anything else come to mind?

1:04:06I think I did. No, my favorite one is like what questions do you have for me? By far. Great. What are some favorite products you've recently discovered that you love? I guess I'll just mention I don't think it was far as my folly's favorite products, but there's two that come to mind. My wife's computer broke the other day and I realized it was the CPU cooler that went bad. And the Corsair H60 CPU cooler was like super easy to use and really adaptable to lots of other boards. I thought that was great. My other favorite product is the one I'm wearing in my ears right now, which my first pair of nice headphones I ever bought died last week late last week.

1:04:41I had to do like some really quick research into my new favorite pair of headphones and these focal baths. These are like super nice. I'm a bit of an audiophile. I like to listen like classical music and ambient stuff. So we need a lot of dynamic range and these and you know, noise cancellation and these have been like great so far. Okay, so what is it? What are they called? Focal I think it's bath as B -A -T -H -Y -S. Okay, and is there a specific model or there's like that one? That's it. Okay, you'll know when you see it. Okay, we will link to them and show notes and maybe I'll get one. What's something relatively minor you've changed in the way that you built product that has had a lot of impact on your team's ability to execute?

1:05:20Maybe the most recent innovation sort of at Rippling was the kind of introduction of what I'm calling imperatives, these things that whether they come bottom up or top down are things that like everybody across the entire product and engineering team needs to do. And what's important about that list is the things that are not on it. And in a world where you know, we could choose to do hundreds of things at once like being able to to kind of force rank that list of things draw a line and say these are the ones everyone has to do has created a lot more focus and clarity than than we had before. So imperatives are essential.

1:05:49Like here's the priorities for the next say quarter or six months here. The these here are the priorities for everybody and now integrate that into your own team's priorities. So each team like stills building like their own priorities but like like have to factor in like this set. How many of those do you usually have? This is awesome. I like this tip. It depends on what level of granularity you want to talk about them at like like maybe 10. It's a lot. We're going through like between like globalization and like large improvements to the platform and like a bunch of other you know large companies all these things they create a bunch of things that just have to be cross team simultaneously.

1:06:28I think it's a pretty natural part of a company's evolution and we're just in that part of the cycle. So awesome. Final question. What's the question I should ask you that I didn't ask you? I guess what do I do with my kids maybe I have two kids. They're not doing their six. What do I do with my kids? My son I'm a big board gamer and while I didn't push it on him my son he will play board games you know morning to night and so we play a lot of like European like strategy games together and my daughter's not getting old enough that she's getting into them too and so we just finished as a family playing a pandemic legacy and the reward tomorrow night is we get to start playing Gloomhaven.

1:07:10So that's going to be fun. I don't know either game sounds very hard and complicated. They're fun. They're fun. Amazing. Jeremy we covered a lot of topics. I feel like this is a compound podcast episode and so thank you for spending time with me. Thanks for being here. Two final questions. Working folks finding online if they want to reach out. Learn more and how can listeners be useful to you? Awesome. LinkedIn is the easiest way online and you know what I've been talking about today sounds interesting to you. We're definitely hiring like senior entrepreneurial PMs and so if those leadership principles on our website look interesting I'd love to hear from you.

1:07:46What's the best way to explore those roles and apply? The website has by far the best channel it gets to this right recruiter who will tell me about it right away. Great surflean .com and there's probably a site for careers. There's a career site on there that you pretty easy to find. We'll link to that in the show notes. Jeremy thank you again for being here. Thanks so much for having me this was a lot of fun. Bye everyone. Thank you so much for listening. If you found this valuable you can subscribe to the show on Apple Podcasts Spotify or your favorite podcast app. Also please consider giving us rating or leaving a review as that really helps other listeners find the podcast.

1:08:22You can find all past episodes or learn more about the show at Lenny's Podcast dot com. See you in the next episode.