Lenny's Podcast: Product | Career | Growth - Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)

Starting point is 00:00:00 It's very, very tempting to kind of float up here as a leader and say, hey, you know, you take that hill over there, you guys do this over here. When in fact, like where you really learn where the challenges are, the problems or the successes is by like just like being there with with the people in the trenches on like one of the things, like whichever one seems hardest or most complicated. And so I try to do that as often as I can. And I found that I always learn a lot by going through that detailed exercise. Welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today, my guest is Jeremy Henrickson. Jeremy is Senior Vice President of Product at Rippling, where he leads to the product and design teams.

Starting point is 00:00:47 Previously, he was chief product officer at Coinbase, where he oversaw 10x growth of the product and engineering organizations and helped scale Coinbase during one of the craziest times in the crypto markets. In your conversation, Jeremy shares his lessons about maintaining velocity and at scale, creating a culture of fast decision-making, the importance of product leaders going deep on a problem, and becoming world experts at their domain, what's a look for in product managers you're interviewing, why relying on frameworks can be so detrimental to your success, why you may want to avoid MVPs and instead design for the most complex use cases first,

Starting point is 00:01:20 and tons more. Enjoy this episode with Jeremy Henrickson after a short word from our sponsors. Today's episode is brought to you by Miro, an online collaborative white, board that's designed specifically for teams like yours. The best way to see what Mira's all about and how it can help your team collaborate better is not to listen to me talk about it, but to go check it out for yourself. Go to mero.com slash Lenny. With the help of the mirror team, I created a super cool mirror board with two of my own favorite templates, my one-pageer template, and my managing up template that you can plug in play and start using immediately with your team. I've also embedded a handful of my favorite templates that other

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Starting point is 00:03:08 Explore plans for teams of every size and see what MixPenel can do for you at Mixpanel.com slash friends slash Lenny. And while you're at it, they're also hiring. So check it out at mixpanel.com slash friends slash Lenny. Jeremy, welcome to the podcast.

Starting point is 00:03:29 Thank you so much for having me. me. I'm excited to be here. So I've heard nothing but amazing things about you. And I'm excited to learn from what you've learned from your experience at Rippling, at Coinbase, and all of the products and teams that you've built. And so thank you again for being here. Yeah, super happy to be here. So I want to start with your time at Coinbase, where your chief product officer, and your chief product officer during maybe the craziest time in the crypto markets, it was I think 2016, in 2018 when I was looking at the Bitcoin prices and it was like, it went from like a thousand dollars to $20,000, I think, in a matter of months. So I'm curious, what was that experience

Starting point is 00:04:06 like? And in particular, what was like leading a product team through that experience? The strongest memories for me, for me are during like 2017, where crypto, which had kind of been at its nadier in like early 2016 and kind of slowly started climbing out, I'm just going took off and became a real thing in the in the public consciousness and you know coinbase which at the time had you know an exchange just like on ramp and off ramp from fiat to to crypto and back experienced over the course of 2017 40x growth in in usage that's like a dream come true for for a lot of people it's no i mean it it was it was both a dream and a nightmare um you know and i was i was incredibly lucky to be working on it with a with a team of people that i could really

Starting point is 00:04:52 trust and could stand shoulder to shoulder with in the trenches. And it was a lot of learning about how you can rapidly scale systems over time. And, you know, people like to trade crypto on Saturday mornings. So a lot of Saturday mornings. There's like some new like thing would break on the edges of the system. And we need to kind of get in there and and work on it. And so it was just a lot of really incredible lessons about who you choose to work with and focus and making sure you have the right people in the room with the right time. Okay. So let's actually unpack a couple of those. So focus is really interesting and something people always talk about, but you know, hard to actually do. I guess how did you keep the team focused? I imagine just like, you know, everyone's getting

Starting point is 00:05:36 rich all over the place in crypto. Things are breaking all the time. Like, how did you maintain focus on your team? Well, the first thing is you don't talk about people getting rich. It's like it's a very technical. It's very technical. You talk about, like, it's customers, it's their money, right? And number one, it had to be secure. Right. So there's a guy named Philip Martin in front of mine now, and he's, he's just this amazing, like, security leader at Coinbase. And he was able to always put these, like, decisions that we were making extremely quickly, like, in context, right, and say, look, these are the kinds of decisions we can make and still have it be secure, no matter how fast we need to move. And so security was always, like, the number one thing. And then

Starting point is 00:06:16 the second thing is like focusing on like the the both the kind of immediate nature of the issue hey site is down or whatever I'm like resolving that but also trying to set those in a context of like where we need to go over the next six months like what are we actually shooting for what do we believe the volumes are going to be what's it going to take to to have you know everything from a user experience to kind of the deep back end of the product that would actually work for that what was maybe the biggest challenge as a product leader trying to keep people focused and everything on the rails as things were going 40X. I think the biggest challenge was that in crypto,

Starting point is 00:06:53 there's just so much uncertainty in general. Like, simple questions like, is Ethereum going to be a thing? Right? Are the subject of debate? And no one actually at the time had an answer to that question, lots of really strong opinions. And so you have to be able to have those debates because lots is going on.

Starting point is 00:07:11 But then you have to be able to come out of those conversations with a clear kind of company point of view. that you're all shooting toward. And while there may still be differing points of views and debates that happen on the margins, you go full speed toward this answer until you decide to go full speed toward a different answer. And I thought we were pretty successful at that at Coinbase,

Starting point is 00:07:30 and it wasn't always easy. Maybe just the last question there. Sure. Living through a time like that, a lot of people are going through these periods of just like intense work, and it's like, holy moly, this isn't crazy stressful,

Starting point is 00:07:42 working like incredibly long hours. But then you, you look back at those times and end up being some most important meaningful periods of your career. I guess one is that is that your experience too and then two I guess is there any advice for someone that's maybe going through something like that of just like here's maybe the silver lining of being in a period like that. So it's hard right. It wasn't wasn't always easy. I had like a new daughter who had been born just a few months earlier right really tough to like kind of balance balance those things, but I've always loved the rate of learning. And so, like, those, it is those

Starting point is 00:08:20 experiences I feel that, like, have most sort of accelerated my own personal growth and personal learnings because it's in the crucible of things being hard. And so I think when people are going through those times, it's nice to take, like, you know, a step back and talk with friends or whatever about, like, what's really, what's really going on and setting it in the context of, hey, you know, three, four, five years now from now when we look back on the history, realize, wow, you know, we, A, we did something amazing with that time. And B, we learned a lot and we were able to take that with us kind of into the, into, you know, whatever we were doing next after that. Before our chat, I asked you what people ask you for advice most around. And you said that it's,

Starting point is 00:08:58 that people often ask you for advice on how to maintain velocity at scale, which is something every founder and product leader is always striving to do. And so what have you learned? And what do you tell people about maintaining and maybe even improving velocity as you scale. I think there's a lot of different answers here. And I think a lot of them are very specific to the nature of the business that someone's in, right? Different businesses can maintain velocity in different ways. I think there's kind of a universal truth that you want like small teams with clear missions. Right.

Starting point is 00:09:28 You know, if there's 300 people trying to work on one thing, like the just sheer like communication challenges, Dunbar's number, all of those things come into play. and it's really, really hard to act quickly. And so having smaller groups of people, breaking down what is always a very, very large problem into, like, sufficiently small bits that small groups can attack wholeheartedly and minimize, like, horizontal communication,

Starting point is 00:09:53 I think is the first thing. I think the second thing is that to the extent it's like a technology problem, the more you can bake into, like, a clear platform, it reduces, like, the decision-making complexity for everyone who's working on, like, the domain part of the problem. And so like a clear platform with a clear interface, you can, easy to use and all the ways that both engineers and product people want it to be easy to use,

Starting point is 00:10:16 simplifies the space in which people have to think about these problems. And that's not always easy, right? If platforms are not, you know, you can't just like write a platform and hope it's going to work for the products. It's very much an iterative thing. But the more one can invest in that and have the right kinds of people who are capable of doing that sort of both systems thinking and product thinking simultaneously, I think is really important. The third thing, just from a leadership point of view, is, like, diving deep, right? Like, it's, it's very, very tempting to kind of float up here as a leader and say, hey, you know, you take that hill over there, you guys do this over here. When, in fact, like, where you really learn where the challenges are, the problems or the

Starting point is 00:10:57 successes is by, like, just, like, being there with, with the people in the trenches on, like, one of the things, like, whichever one seems hardest or most complicated. And so I try to do that as often as I can. And I found that I always learn a lot by going through that detailed exercise. And I think the last thing is just making sure that teams have like the right distribution of like experience and seniority. Like sometimes you get a team started and the team is like perhaps doing something that's like zero to one.

Starting point is 00:11:25 And they're amazing at all this zero to one stuff. And then like two or three years later like those same people are trying to like scale the product to like, you know, millions of people. And it turns out that, A, they don't like. they don't like that part of the job as much. And B, maybe they're not as good at it. So I think you just constantly like look at the team and make sure that, A, people are doing things that they love.

Starting point is 00:11:44 And if they're not, like, hey, I've tried this other thing instead. Right. And B, like, recalibrate the team and make sure like the right kind of skillsets are there. And I found if you kind of do all of those things and then have product leadership where we're saying this is what we need to do, right? And very, very clear and precise on what needs to be done. Then you can usually actually even accelerate over time because you bake more into this platform. It allows your engineers to do more with less, and that's always pretty amazing.

Starting point is 00:12:07 Okay. Let me dig into a couple of these. These are really great, please. So with the small teams with clear missions, is there an example of that at Rippling our Coinbase where that was like a really good example of this being true? One example is maybe three years ago when I was just starting at the company, we decided that we needed to build a time and attendance product. Lots of market demand for us. that we hadn't built it yet, something that many customers need. And so there were a bunch of ways we could have chosen to do that. But the way we did it was to say, look, let's find one engineer, really talented systems engineer who's actually capable of doing product thinking, and have Parker,

Starting point is 00:12:49 CEO, also spend time on it. And you start there, right? And Satchath brought a few people on with him. And those four people over the course of maybe nine months or so built a time and a 10 product. It was the only thing they were doing. They didn't have to worry about what was going on with our payroll product, except to the extent they had to integrate with them a little bit, right? They didn't have to worry about what was going on with the kind of the benefits team or kind of our IT products. They were, they were monomaniically focused on this one thing. And then identifying the places where, yes, there's connectivity to the rest of the suite. And that allowed them to move extremely quickly. How much of that was Parker being on the team helping them unblock everything versus being

Starting point is 00:13:28 very small and focused? I think it was mostly small to focus. Like, obviously, Obviously, Parker can, like, do things and unblock them in the way that only a CEO can, and that helps. But the thing is that, like, we've now replicated that, like, you know, a dozen times, right? That's our model for starting new things. And so it can't just be him unblocking things, though he does unblock things. It's more that, like, this pattern of having these small groups, like, be able to do things. And then being able to, like, go to those people, right, whether you're Parker or somebody else in the company and be able to say, A, how are things going?

Starting point is 00:14:00 or are we working on the right things or let's see the latest designs for that thing and comment on it? All of those things can happen just at a much greater tempo than if you're like trying to go three layers down into the org and do things. I think that's the other maybe the key point here

Starting point is 00:14:14 that like everyone is exposed to senior leadership. Like yes, we have like a management structure because you have to. But that management structure does not interfere with the ability of kind of anyone anywhere in the organization to kind of like look at what's actually happening and that happens very directly. So let's talk.

Starting point is 00:14:30 about that model. You just described, so what is that model? So this is how you approach new products. And I know within Rippling, there's many, many products and features we're going to talk about this. And you're saying that you have kind of an approach to adding a new business unit, essentially, or a new product feature. What is what does that model roughly? Yeah, so the model's quite simple. In the vast majority of cases, we realize we need to build something. And we have, you know, the one-page view of what that is. And usually we're lucky enough that the things we're building sort of exist in some form in the industry today, not in the different. differentiated way that we can build it. But like time and attendance is an example, like,

Starting point is 00:15:03 that's a well-known thing in the industry. There's whole companies that do only that. Right. So we start there. We find a single engineer who is extremely entrepreneurial, understands what it means to operate at tempo, understands what it means to like make decisions with low information, understands how to work very, very quickly with like a design partner. So we have a design partner. And we say, look, come into Ribbling, spend a few months getting to know the platform, first of all. So go work on. this other team, understand what's easy for them, what's hard for them, how the platform works, how other products have been built on top of this. Go talk with other people who founded products

Starting point is 00:15:40 here and understand what their experience is so that you can learn from and iterate on it. Get an opinion about your product and then start building it. And during this intervening time, they're also recruiting, right? A team of usually two, three, four other engineers who kind of have that same zero to one mentality. And they start building. And, uh, you know, usually over the course of like six to nine months, we can get a product from, you know, a blank sheet of paper to something that is launched, or at least that we're using sort of internally

Starting point is 00:16:09 when we dog food our stuff really heavily. And then it grows from there. And then sometimes when you launch one of these products, we get close to launch, you realize, hey, actually a team of five or six people can, like, kind of handle this product. At Nauseem, sometimes you have to bump it up. It's like, okay, this thing's about to go to production.

Starting point is 00:16:24 There's all these other things to do. The team now needs to go from four to 15 or something like that. really depends on the product. But that's the general life cycle, and then you keep growing and scaling it. That is fascinating. So just to understand, you find a founder type to kind of take the lead on a new idea. And do you recruit them internally or you sometimes find them externally just to focus on this product? Both. Both. Okay. And then you find a design partner for them to work with to figure out what exactly needs to be built. And is the idea pick one design partner or you try to encourage a few? Usually it's one. So there's a designer, right?

Starting point is 00:16:59 So we have a design. Oh, design partner, meaning a designer, not a company that is like their partner and design. Oh, no, no, no. Like literally somebody who, who knows Rippling's products, knows like our component library knows all that stuff and is skilled and like doing, you know, UX and interaction and visual design. Got it.

Starting point is 00:17:20 Okay. Designer. Okay, cool. And then they basically, with maybe a couple engineers, just that's the team. that initiates a new product line and then launches it and then as it scales, maybe grows the team, maybe not. Yep, that's right. And like, you know, every, you know, it's pretty ad hoc, but every couple of weeks or

Starting point is 00:17:37 something like that, they're meeting with like me or with Parker, you know, whichever one of us is like the DRI on it and like giving feedback on the designs, kind of having a critical lie for like, oh, man, if I were using this as an admin, you know, a small company or an admin of a large company, how would I feel about this? Would this interface work for me? And so we were pressure testing it like kind of throughout, throughout that cycle and trying to get the balance of like, you know, speed and comprehensiveness right. This reminds me you're also, I hear not a big fan of MVP's that you like building products to further to a further point. Is that true?

Starting point is 00:18:12 And then if so, how do you think about the initial version of a product? First of all, I don't want to knock on MVP. I think MVP is like have their place. They're extremely useful, particularly if you're, you know, literally at a zero to one. company that's never done anything before and you don't have like clear market validation. I think in our case specifically for Rippling, a minimum viable product would do a disservice like to both our customers and to like the very team that was building it. And the reason I believe that is that when when you design a minimum viable product, you're optimizing for speed.

Starting point is 00:18:46 And in that set of optimizations, you are minimizing the deeper product thinking about what can like fully differentiate our product based on not only existing kind of capabilities within our products and platform, but based on what it ought to do in the future. And so it sort of limits product creativity, but worse, it leads to building the wrong thing technically. Right. So if you're only thinking through the simple cases and you're an engineer and no one's pushing you on saying, wait, what about that, you know, healthcare hospital administration case where like, you know, it's mission critical in life, then you're going to make a different set of architectural assumptions. And then you're going to build on those. And you're going to build on those for six months,

Starting point is 00:19:32 nine months a year. And you'll have dozens or hundreds of assumptions built on top of those. And it's extremely difficult to unwind those decisions once you've built them into the product. And therefore, you know, we believe very deeply. It's like, sure, understand those simple cases, right? understand if you're a two-person company, you don't need all of these other things and what is the product that will look like for you to approach it, but also understand what it would mean to have 10,000 people globally around the world with this like ridiculously hard use case. What's the model that would support that? And let's make sure that as we're doing the technical and product design for this thing,

Starting point is 00:20:14 that it accommodates that view, even if we're not going to support it in the first version, right? Even if we make like the product decision to say, like, look, we actually, actually don't need to handle that case right now, you still build the product in a way that's not going to prevent you from getting there in the future. And does that take a little more time? Sure. Yeah. But does it save you time in the long run? Absolutely. Right. And so, so that's our approach. Is there an example that it comes to mind of product you build at rippling or coin base of just like, it could have been this really simple MVP and then ended up being like, no, we did the right thing

Starting point is 00:20:47 by building it further along the spectrum. Yeah, so I think a great example of this at Rippling is our global payroll product, right? We could have said, hey, look, we just need to support this one country, right? We need to support whatever, the UK, let's say. So we're going to copy all of our U.S. stuff, like just replicate it, and like change all the things to be U.K. like,

Starting point is 00:21:12 that would have been the fastest thing to do to dramatically oversimplify, right? But that's not what we did. What we did is we said, look, we need to launch with six countries. And these are six super different countries that we want to look at. And they're going to have different requirements from like an HRIS standpoint, from an employer of record standpoint, from how you pay global contractors, from how payroll works. And we're going to make a system that works for those countries.

Starting point is 00:21:37 And there's like lots of downstream implications for that. But what it means is that now our global payroll system, adding a country, is not easy. but it's a lot easier than it would have been if you had to continue to stamp out and replicate and then of course maintain all of these things that have very little underlying connectivity. And instead what we have is like, you know, 80% of the system is baked into our global payroll platform.

Starting point is 00:22:02 And then like the 20% is like country specific. And most of that specificity can be had a lot by engineers, right, who are very, very expensive to change things that are like local specific, but instead can be configured by somebody that's in compliance, by somebody that's in legal that needs to get the right documents into the system. And all of that stuff can be handled by the system, which allows us to move much faster, sort of going forward.

Starting point is 00:22:26 I've heard you describe this kind of idea as you encourage teams to design for the most complex use case first. Is that kind of the instruction you give these teams? 100%. Many times. So it's one of these things that, like, until you're here, it's a really difficult thing to kind of grok because, A, it's so counterculture to what, like, the background that most people will. come from. It's like, no, no, no, don't think about all those things. Just like zoom in on this,

Starting point is 00:22:49 on this one case, use it as a wedge and then grow from there. And this is one of the reasons that we have people, especially new people in these kind of founding roles come in and spend a few months just like absorbing the culture to like really, really learn, really learn these lessons. And it's one reason that we're extremely high touch with kind of new products in their infancy to make sure that we just don't fall into that trap, right? Especially because like simultaneously with doing this, we're like, hey, but we need to ship this as fast as possible. Right. And so you want to get the balance of those two things, right? So when I think about Rippling, I think of you got kind of the culture is to do things the hard way and the right way.

Starting point is 00:23:24 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 product and organized teams and all the things you were just talking about about MEPs and, you know, build new products? The idea of a compound startup for us is that we're basically a lot of business. businesses that all work together, right? Like, if you think about the products we offer, we have payroll, well, there's entire company is built just on payroll. Insurance and benefits, entire companies, that's an entire life. In fact, like a fragment of benefits is the entire lifecycle of the whole company. You know, our IT products, device management, identity management,

Starting point is 00:24:04 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, you know, 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 and is impossible to keep in sync everywhere. The right answer is 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.

Starting point is 00:24:42 So the idea of a compound startup is like all of the, these different businesses benefit from being built on top of one platform. The activation energy for that is extremely high. So before my time at the company, Parker, Prasana, the technical founder and others built all of the first versions of all of these products. And it was a minor miracle. They were able to do that. But 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, on top of that. On top of foundation. This touches on something that comes up a number of times in this podcast, which is the importance of differentiation. And it feels like this is the differentiator for rippling. It's not going to be

Starting point is 00:25:24 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? Or is there a different way to think about that? Yeah, I think that's right. So, I mean, the 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. You can't build out a, I don't know, a permissioning system that looks at the various attributes

Starting point is 00:26:05 across all of these products. You now suddenly have to do an integration in each of these products talks different languages. You 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

Starting point is 00:26:29 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 in the system, immediately knows, right? And that's a very, very simple example of something that that you can only

Starting point is 00:26:49 do if you start with, like, solve it to come back to an 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 Ripling's culture that maybe you haven't mentioned yet. I would say it's fundamental speed of execution, right? I 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.

Starting point is 00:27:28 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 Slack 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, the speed of response. And no company I've been at in any scale, five people, you know, 5,000 people has ever operated at the tempo this one does. And I think that our ability to continue to operate at that tempo, which is partly

Starting point is 00:28:06 due to the fact that we are a compound startup and have these small teams 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 like little tidbits of advice. And one of his pieces of advice is that usually the best time to do something is right now. And that feels like that resonates with the way you all think. I'm curious just how you create that culture and ability to make decisions fast. Is it purely top-down founder?

Starting point is 00:28:35 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, he likes making decisions quickly, and it's also a deliberate strategic decision on his part

Starting point is 00:28:51 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. And 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 as something that kind of everybody promulgates. But also, I think there's a number of things we've done to sort of like bake it in, right?

Starting point is 00:29:14 Like in the way that we, you know, 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? In product, you don't own like, little feature. You own, like, your product. and you're expected to be the world's foremost expert in it. And 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 to look something up.

Starting point is 00:29:46 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. And if you don't, then we're going to move on. That's right. And so, and so, and so, and it's, it's shocking to people when we actually move on, right?

Starting point is 00:30:10 That haven't been here yet. It's like, no, no, that date passed. You don't, you don't get to, like, retroactively, 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, just means it's, like, gets reinforced on sort of its own, out of its own gravity. Do you have values, like internal values that you've kind of outlined that are a part of this?

Starting point is 00:30:39 Or is that not something that you find super valuable? No, we actually, I find them quite valuable. And actually our C.O. Matt McInnis, 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 with on Rippling. There's a sort of Rippling leadership principles. You know, there they are. And they are really true to the culture of the company.

Starting point is 00:31:00 The way we came up with them was to us, you know, a couple years ago to, to introspect and to what actually made people successful at the company. Like, 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 it here? And, like, those are the things that are differentiating. And those are 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'sjobs.com slash talent. hiring manager, you can sign up and get access to hundreds of hand-created people who are open to

Starting point is 00:31:38 new opportunities. Thousands of people apply to join this collective, and I personally review and accept just about 10% of them. You won't find a better place to hire product managers and growth leaders. Join almost 100 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 space. specific companies. You can also leave anytime and you'll only hear from companies that you want to hear from. Check out Lenny'sjobs.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. What

Starting point is 00:32:21 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 whoever is in the role of like making the top level product decisions, right, of them being, one, extremely clear about what those priorities are and more importantly, extremely clear about what all the priorities aren't, right? Like, there are so many things that, like, could be important or people can make the case for being important or whatever that, like, are fundamentally distracting from, like, the core mission of getting something done.

Starting point is 00:32:55 But secondly, for that person to go all the way to ground on it, right? We have one of the leadership principles is go and see, right? So to look at the thing and then like walk all the way to ground and like talk with the engineer who's like writing the code on the thing. Because inevitably this top level communication is insufficient to get to like the detail of like what matters and doesn't matter. And 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 sort of across the board and like forces everyone to sort of like up their game a little bit and just helps people understand what the expectation. is, right? And I think in the absence of those sort of clear expectations, it's difficult for people to, like, perform at their best. Right. And so 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 end of what's possible. A recent story was I.O. talking about building the cash card and going to, like, the warehouse and watching the printings of the cards. and things like that.

Starting point is 00:34:03 Yeah. I guess, first of all, do 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 to do that and that leading to something really important?

Starting point is 00:34:16 In the early days of our kind of global efforts, right, when we were first trying to figure out, like, 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 U.S. But our kind of head of payroll went in and said,

Starting point is 00:34:31 like actually here are the ways in which like we knew 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 fulsome experience. And that then backs into things like, well, every country does tax filings. Every country does them slightly differently. But how are we going to build a tax filing system?

Starting point is 00:35:01 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 like 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 over time. And so the leader of that team basically just went and studied the tax laws of each country.

Starting point is 00:35:36 That's right. Like went all the way, like went all the way to ground. It's like, okay, like let's go and open up the big old like, I mean, it's like online these days with a big old tax book and look like it's like, or when you're in the United States, it's 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 whatever they call them right they 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

Starting point is 00:36:16 ground and looked at how these things are actually actually worked how they're communicated and 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. And 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

Starting point is 00:36:51 and tell me. And I think what you're saying is you go do that and learn become the world expert. 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 like 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 taxed right that's what they're that's what they love and that's what they do but that doesn't make them necessarily a great product thinker right so the person of 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

Starting point is 00:37:25 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 or 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? I think it's an equally, you know, if a job is 80 hours a week, it's like 40 of your hours. Like it's, it's, I think, I think 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 the other half of the job of communicating with the engineering team and writing documents or whatever.

Starting point is 00:38:03 But what's the point of writing a document if you don't know what you're talking about? 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. We expect like a single leader to be able to know 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's kind of just an amazing, amazing place to be.

Starting point is 00:38:42 I'm looking at this list and I just want to keep asking questions about it. One of the 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 design 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 particularly for a product org, right? Because product leaders have to be right most of the time because their decisions reflect

Starting point is 00:39:13 across the entire org and their decisions fundamentally spend time, right? And 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 an ambiguous information with an ambiguous situation with incomplete information and 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, ah, I don't know. That feels wrong for this reason, this reason. If they have like the confidence to like make that call and then a year later when you look back on it for them to have been right.

Starting point is 00:39:55 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, was this person, like, usually right in respect and 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?

Starting point is 00:40:20 Either you're really, really good at making those kinds of decisions or you're not, right? 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 this lines, because a lot of companies start, you know, one country, most companies do.

Starting point is 00:40:40 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 kind of your algorithm for that? So it starts with the assumption that we're going to have to be everywhere, ultimately, right? That you don't actually have to build, like, native global payroll in every country in the world. It doesn't make sense to do that every country in the world, but you definitely want to be able to pay people in any country in the world,

Starting point is 00:41:08 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, when we made that decision to have quite a few customers already, like thousands of customers. And so we knew not only where their kind of U.S. employees were, but by virtue of being an employee system, where they actually knew where they had other employees. And so it was quite easy for us to say focusing on U.S.-based companies,

Starting point is 00:41:33 which is incomplete data, right? But if we just look at our U.S.-based companies, we know that there is immediate demand for those people to pay people in, you know, countries, X, Y, and C. And we just like listed those out in raw numerical order. And then we kind of looked at, okay, how hard is it to build in these countries

Starting point is 00:41:50 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 is there risk, right? Where is this, where is this hard? Where is 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 stack 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 reordered those over time. And as we've

Starting point is 00:42:19 doveed in the countries and learned more, you know, we rejigger things like a little bit. But for the most part, like that same basic list we started with is still like, you know, mostly right. Okay. And then the other question, a lot of founders always struggle with is when is a time to start expanding internationally? Because, you know, there's pros and cons. Do 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, right?

Starting point is 00:42:59 Just as we care if there's not a you in color, right? There's just like all of these subtle lessons that like cultural lessons for companies that take like a really, really long time to absorb. And so my view is you always should do it earlier than you think you should, then 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.

Starting point is 00:43:22 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. It just 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 notice that too. And you saw other companies starting to try to address parts of this 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

Starting point is 00:44:04 thing. What have you found to be most surprising about expanding internationally to be successful in expansion for folks that are maybe starting down this road of like, oh, shoot, we should think about that? I think the thing that was most surprising to me, the first time I did this back at Guidewire in the in the aughts. 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 U.S. 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

Starting point is 00:44:50 things like they're being a you in color or not, or, you know, if you ever see a demo delivered to somebody in another country where they see like a detail screen about a person that it includes a social security number, it's like that you immediately lose credibility. It doesn't matter how good all the rest of your stuff is. And 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 a German system or something and like demoed it in the United States with like poorly translated stuff we would think it would suck to, right? And so, but it's not, it's really hard to adapt to that mindset. And, and so it takes just a lot of energy to, to kind of overcome that organizationally.

Starting point is 00:45:32 Makes tons of sense. I'm going to go in a different direction now. Sure. Frameworks. So I know that you're not a huge fan of frameworks. We were chatting about this before we started recording. And so I'm 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'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. Right. So I like to have just enough process to create a frame, right, so that the right decisions can happen and like no more. I think there's a danger, especially as company's scale, that you end up saying, well, you know, if only

Starting point is 00:46:17 we categorize, you know, everything correctly and Jira, like, you know, we will be able to make, like, really good prioritization decisions. I'm like, sure, extremely helpful to have clear categorization and things that jurors 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. And so, so I think the right answer, the right amount of process for any given team is, like, or the right framework for any team is really just dependent on like their specific life cycle. So you won't see me saying like

Starting point is 00:46:49 oh we need to use like this scrum thing or that combon 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

Starting point is 00:47:05 if those are different for different teams. And the only place I care about unification is one on the quarterly planning process and two like everything does need in fact to be in Jura because Otherwise, you can't rationalize about what's actually getting done and not. Is there a process or 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.

Starting point is 00:47:26 Or generally, it's like, let's just rethink everything ourselves. No, I don't find one to be particularly. I haven't consistently found one to be particularly problematic. I think any framework sort of has this place, you know, right place, right time. I think there's danger any one time somebody like dogmatically says, I think we should use process X because that's all. almost never the right answer in my experience. I think there are places where that can differ.

Starting point is 00:47:49 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 think they can be really, really great. And like 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. I think it's kind of different in the product world.

Starting point is 00:48:08 If you had to compare the way Coinbase built product process-wise or just product development process-wise to Rippling, what would you say are the bigger differences? I 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 at CoinMas around like having those debates and like getting

Starting point is 00:48:35 to a decision and disagree 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. And 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 just continuously better than everything that's out there? And that, like, yields a different decision-making process.

Starting point is 00:49:01 So for me, it's like the mental model is actually of how I approach those things are the same, but they just, like, yield different results in the actual making of the software. what is that actual difference do you find like day to day? Is it like timeline differences? Is it how quickly, I don't know, the way you 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, pick a random team.

Starting point is 00:49:36 If you're on the device management team, like you know what you got to do, right? there's no ambiguity or 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. It'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 higher here, which does not say people work harder or less hard at Kormuzzi. Like, Kournios was like an amazingly fast, like, environment, but it was also subject to the fact that, like, you just don't know what the

Starting point is 00:50:14 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 reactivity to, like, the environment and the crypto environment, what's going on and the uncertainty of the regulatory environment, all that stuff. We are really, really, really good at handling those things really rapidly, which is something that we need to handle somewhat less, puribly. Sounds quite stressful at Coinbase. Yeah, I mean, it was it was fun. Yes, so stressful. I mean, every job I've ever had has been stressful,

Starting point is 00:50:45 but 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, that's why I stayed at these places, right? And so, but yeah, it's stressful. And looking back, what a joy. Yeah.

Starting point is 00:51:03 There 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 I've been so lucky to be a part of. And 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 hardships and then you look back and you're like, wow, that was so cool.

Starting point is 00:51:25 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 at a startup, your life sucks for two years and it doesn't work out. and that there is a lot of upside and good memories to that, but it's less, it's less glorious. Yeah, that's fair. Though, I mean, the, the first company I was really at kind of out of school's company called reactivity back in internet one era. And we were trying to figure out, like, how does this internet thing work? How do we start companies on the basis of these technology technologies? How do we help other companies, like, build stuff and figure it out? you know, and that company, like, fundamentally, like, didn't work out.

Starting point is 00:52:02 Ultimately, God kind of spun itself out and got acquired, 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 learnings I had there. And then the people I had a chance to work with was just really exceptional. So I feel very lucky. That's a really good point, actually.

Starting point is 00:52:32 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.

Starting point is 00:52:49 So you've hired a lot of PMs over the years. I'm curious what's something you've learned about what to look for in product managers and also just in product leaders that other people may not. to be focused on us, you know? I mean, I don't know that I have any, like, particularly special insight here. I think there's a couple things that I do ask that I, 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,

Starting point is 00:53:14 there's a part where 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 opportunity. or in the case study, there's a lot of opportunities. So just like ask ad hoc questions or to like change one assumption. And seeing how people react to that is really indicative of how deeply they understand,

Starting point is 00:53:42 you know, a new problem or how quickly or how mentally agile they are. And, you know, and some people are extremely good at that, like, here an assumption and they like blink a couple times. They're like, oh, well, that has like these 400 implications, right? And they just start rattling them off. And some people get like really flummoxed, 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 the questions that people ask, which is indicative of, number one, they're, like, actual interest in the job, right?

Starting point is 00:54:14 Like, people tend to ask better questions when they're, like, more excited about working out 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 quality to be the same all time. But like, sometimes people ask a question like, oh, man, I would have never thought to ask that question. That's such an insightful question. And then I pause.

Starting point is 00:54:34 And I have to think about my answer a little bit. And so it kind of pushes me to be a little bit better. And when that happens, I know I usually have 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 and like, oh, wow, that was great. I remember about three years ago, I was interviewing a guy named Kyle Boston. and Kyle is now,

Starting point is 00:54:56 now runs our platform product organization. And I can't remember the specific question he asked, but it had something to do with, wait a minute, if you have all these products and you have this

Starting point is 00:55:10 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,

Starting point is 00:55:21 permissioning else. And this was before we'd like fully formalized the concept of our platform beyond the kind of employee system of record. And I remember thinking like, yes, yes, we should. And, you know, that had entered our minds before, but the fact that somebody who had like almost no context on the company, right, 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

Starting point is 00:55:44 interviewing with a 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. and his ability to kind of think through the sorts of things we need in to think through. And I think it touches on PMs need to be business leaders. And great questions are often about

Starting point is 00:56:04 the business and the future of the business and how to make it run more efficiently. And there's like a product org element to it. But I find that that's like a really underappreciated element of PM interviews 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, right?

Starting point is 00:56:21 And having the context like around, you know, whether it's like revenue questions or strategy questions, but also like the detailed questions, right? It'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 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 to help them think through those details is really cool. You talked about this prompt. 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

Starting point is 00:56:57 is like a good example of a type of prompt to give a product manager candidate? In 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, get in 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, modulo, other conversations around the edges. And the questions that matter are around,

Starting point is 00:57:35 like, how do people think through that product discussion, right? Which 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, 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

Starting point is 00:58:03 that people have thought through or not thought through or kind of the depth of their 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. But it is a very strong signal when people, you know, whether they've thought through a set of questions they want to ask or just like, you know, on the fly, like generating them,

Starting point is 00:58:21 you learn a lot about how people think about product, about what they're looking for, about 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 and advance their career most

Starting point is 00:58:38 in the early part of their career? Be humble. Being a product person means that, 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. Right. And so having, like, no matter how smart you are,

Starting point is 00:58:56 there's a lot of 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 this stuff and coming to different conclusions. And so I found that that humility is one of like the biggest differentiators

Starting point is 00:59:17 in early career product leaders who sort of are, able to let go of like how awesome they were in school or in their first job or whatever. I mean, I had to do this. And 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 how many 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. This 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.

Starting point is 01:00:02 Very simply. I 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 being able to be an 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. incredibly powerful. Final question. You've brought up Parker a number of times, and something that is clear about him is that

Starting point is 01:00:24 he's a very product-minded founder. He has a lot of strong opinions about what products should be. And as a product leader with 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 a product. So my question is just, what have you learned about being successful as a product leader with a founder that has very strong opinions about what the product should be? Yeah.

Starting point is 01:00:47 Yeah, 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. Like, 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,

Starting point is 01:01:13 and I wouldn't be able to work with those people. but yeah Parker is incredibly strongly opinioned but he's also incredibly informed which makes for some really really great debates and I've just found that like whatever it's not even CEO but whatever a manager's idiosyncrasies are you have to find a way to like work with those 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 I think that's actually one of my one of my core skills so and so that's work That's worked out for me. And 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.

Starting point is 01:01:59 But, like, when we don't, we can have a totally reasonable discussion about it. 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 adapting. I 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.

Starting point is 01:02:22 I've got six questions for you if you're ready. All right. I'm ready. Hit me. Here we go. What are two or three books that you've 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.

Starting point is 01:02:42 But like it's about the time like just before and like in. to the Enlightenment, historical fiction, a lot of fun. And I also love the culture series by Ian Banks, which is just like super fun, far future sort of 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, like, I guess a recent movie, it's not that recent, but I really like Tenet,

Starting point is 01:03:12 you know, 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 kind of ended, but we had a drinking game anytime someone mentioned last of us, which took over White Lotus. I'm going to drink some tea right here. Okay, fair enough. I'll try. I've only got water. Normally I got tea, but water did it. It works, but it's interesting. It hasn't come up often. So I think maybe we end that for now and see what the new pattern emerges. Yeah. And then Tenant.

Starting point is 01:03:42 feels like, I was just thinking, it feels like a compound movie. Compound startup as a movie. That movie is very complicated to. Yeah. I enjoyed it. I liked, I like trying 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 I'd like to ask? You already maybe answer this, but anything else comes to mind. I think I did. No, my favorite one is like, what questions do you have for me? By, so. Great. What are some favorite products you've recently discovered that you love. I guess I'll just mention, I don't think as far as I've called these favorite products,

Starting point is 01:04:18 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 H-60 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. and had to do some really quick research

Starting point is 01:04:42 into my new favorite pair of headphones and these focal bathies are like super nice. I'm a bit of an audio file. I like to listen to like classical music and ambient stuff. So we need a lot of dynamic range and these and noise cancellation and these have been like great so far. Okay, so what is it? What are they called?

Starting point is 01:04:59 Focal, I think it's bathis, B-A-T-H-Y-S. Okay. And has there a specific model or there's like that one? That's it. Okay. You'll know it when you see it. Okay. We will link to them in the show 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.

Starting point is 01:05:20 Maybe 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 kind of force rank that list of things, draw lines, like these are the ones everyone has to do,

Starting point is 01:05:44 has created a lot more focus and clarity than we had before. So imperatives are essentially, like, here's the priorities for the next, say, quarter, six months here. Here are the priorities for everybody. Now integrate that into your own team's priorities, right? So each team, like, still is building, like, their own priorities, but, like, have to factor in, like, this set. How many of those do you usually have?

Starting point is 01:06:06 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, right? It's a lot. We're going through like between like globalization and like large improvements of the platform and like a bunch of other, you know, large companies, all these things. It creates a bunch of things that just have to be cross-team simultaneously.

Starting point is 01:06:29 I think it's 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 have asked you that I did? didn't ask you. I guess what do I do with my kids maybe? I have two kids. They're nine. They're 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 tonight. And so we play a lot of like European like strategy games together. And my daughter's now getting old enough that she's

Starting point is 01:07:00 getting into them too. And so, uh, we just finished as a family playing a pandemic legacy. And the reward tomorrow night as we get to start playing Blue Haven. So that's going to be fun. I don't know. Either game sounds very hard and complicated. They're fun. They're fun. Amazing.

Starting point is 01:07:18 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. Where can folks finding online if they want to reach out, learn more? And how can listeners be useful to you?

Starting point is 01:07:32 Awesome. LinkedIn is the easiest way online. And, you know, if 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. What's the best way to explore those roles and apply? The website has by far the best channel. It gets to the right recruiter who will tell me about it right away. Great.

Starting point is 01:07:55 So rafling.com and there's probably a site for careers. There's a career site on there that 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. Hi, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast.

Starting point is 01:08:22 You can find all past episodes or learn more about the show at Lenny's Podcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)

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