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

[00:00] It's very, very tempting to kind of float up here as a leader and say, hey, you know, [00:06] 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, [00:15] being there with the people in the trenches on one of the things, 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. [00:31] Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. [00:40] Today my guest is Jeremy Henriksen. Jeremy is Senior Vice President of Product at Rippling, where he leads the product and design teams. [00:47] Previously, he was Chief Product Officer at Coinbase, [00:50] 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 our conversation, Jeremy shares his lessons about maintaining velocity 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 to look for in product managers you're interviewing, why relying on frameworks can be so detrimental to your success, [01:20] cases first, and tons more, enjoy this episode with Jeremy Henriksen after a short word from our sponsors. Today's episode is brought to you by Miro, an online collaborative whiteboard that's designed specifically for teams like yours. The best way to see what Miro is 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 Miro.com slash Lenny. With the help of the Miro team,

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[03:24] Jeremy, welcome to the podcast. Thank you so much for having 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. [03:42] And so thank you again for being here. [03:44] Yeah, super happy to be here. I want to start with your time at Coinbase, where you're Chief Product Officer. [03:50] and your chief product officer during [03:52] Maybe the craziest time in the crypto markets. It was, I think, 2016, 2018 when I was looking at the Bitcoin prices and it went from like $1,000 to $1,000. [04:01] $20,000, I think, in a matter of months. [04:04] So I'm curious, what was that? [04:06] experience like [04:07] and in particular, what was it like leading a product team through that experience. [04:10] The strongest memories for me are during 2017, where crypto, which had been at its nadir in early 2016 and slowly started climbing out, took off and became a real thing in the public consciousness. And... [04:26] You know, Coinbase, which at the time had, you know, an exchange just like on ramp and off ramp from fiat to crypto and back experienced over the course of 2017, 40x growth in usage. That's like a dream come true for a lot of people. [04:41] No, I mean, it was both a dream and a nightmare. You know, and I was incredibly lucky to be working on it with a team of people that I could really 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.

[05:11] on the edges of the system and we need to kind of get in there 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 at the right time. Okay, so let's actually unpack a couple of those. So [05:27] Focus is really interesting and [05:30] Something people always talk about, but hard to actually do. I guess, how did you keep the team focused? I imagine just like everyone's getting rich all over the place in crypto. Things are breaking all the time. How did you maintain focus on your team? [05:43] 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. [05:54] There's a guy named Philip Martin, a friend of mine now, and he's just this amazing security leader at Coinbase. He was able to always put these decisions that we were making extremely quickly [06:06] 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 the second thing is like focusing on like 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 have, you know, [06:36] experience to kind of the deep back end of the product that would actually work for them. [06:41] What was maybe the biggest challenge as a product leader trying to keep people focused and

[06:46] everything on the rails as things were going 40x. [06:49] I think the biggest challenge was that in crypto, [06:53] There's just so much uncertainty in general, like simple questions like, is Ethereum going to be a thing? 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. But then you have to be able to come out of those conversations with a clear kind of company point of view. [07:16] 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, and it wasn't always easy. [07:32] Maybe just the last question there. [07:34] 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." [07:42] working like [07:43] incredibly long hours. But then you look back at those times and end up being some of the most important [07:49] meaningful periods of your career. I guess one 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..." [08:01] being in a period like that. [08:03] So it's hard, right? It wasn't always easy. I had a new daughter who had been born just a few months earlier. Really tough to balance those things. [08:14] I've always loved the rate of learning.

[08:17] And so, like, those, it is those 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, [08:32] you know, a step back and talk with friends or whatever about like what's really going on and setting it in the context of, hey, three, four or five years from now, when we look back on this, we realize, wow. [08:42] A, we did something amazing with that time, and B, we learned a lot and were able to take that with us into whatever we were doing next after that. Before our chat, I asked you what people ask you for advice most around business. [08:56] And you said 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? [09:12] 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. Different businesses can maintain velocity in different ways. I think there's kind of a universal truth that you want small teams with clear missions. [09:27] Right. You know, if there's 300 people trying to work on one thing, like just sheer like communication challenges done by a 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, small bits that small groups can attack wholeheartedly and minimize like horizontal communication, I think is the first thing.

[09:57] technology problem, the more you can bake into a clear platform, it reduces the decision-making complexity for everyone who's working on the domain part of the problem. So a clear platform with a clear interface, easy to use in all the ways that both engineers and product people want it to be easy to use, simplifies the space in which people have to think about these problems. [10:22] And that's not always easy, right? 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. [10:42] Right. Like it's it's very, very tempting to 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. [10:59] being there 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

[11:29] 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 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. And if they're not like, hey, try this other thing instead. Right. And B, like recalibrate the team and make sure like the right kind of skill sets are there. 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. [11:59] 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. [12:07] Okay, let me dig into a couple of these. These are really great. Yeah, please. So with the small teams with clear missions, is there an example of that at [12:16] Rippling or Coinbase, that was a really good example of this being true. [12:20] 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 in 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. [12:43] really talented systems engineer who's actually capable of doing product thinking, and have Parker, CEO, also spend time on it. [12:52] And you start there. [12:53] Right. And Satya brought a few people on with him. And those four people over the course of maybe nine months or so.

[13:00] built a time and attendance 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. They didn't have to worry about what was going on with the benefits team or our IT products. They were monomaniacally 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. [13:24] How much of that was Parker being on the team, helping them unblock everything versus... [13:28] being very small and focused? I think it was mostly small and focused. Obviously, Parker can do things and unblock them in the way that only a CEO can, and that helps. But the thing is that Rippling, we've now replicated that [13:40] 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 have like go to those people, right? Whether you're Parker or somebody else in the company and be able to say, hey, how are things going? Or are we working on the right things? Or let's see the latest designs for that thing and comment on it. Like all of those things can happen just at a much greater tempo. [14:08] than if you're trying to go three layers down into the org and do things. I think that's the other key point here, that everyone is exposed to senior leadership. Yes, we have a management structure because you have to, but that management structure does not interfere with the ability of anyone anywhere in the organization to look at what's actually happening. And that happens very directly. [14:29] So let's talk 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

[14:35] 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 that model, roughly? [14:44] Yeah, so the model is 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 differentiated way that we can build it, but like time and attendance is an example. Like 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. [15:09] who is extremely entrepreneurial, understands what it means to operate [15:14] at tempo, understands what it means to make decisions with low information, understands how to work very, very quickly with a design partner. So we have a design partner. And we say, look, [15:25] Come into Rippling, 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 here and understand what their experience is so that you can learn from and iterate on it. Get an opinion about your product. [15:46] 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 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, when we dog food our stuff really heavily.

[16:16] you realize, hey, actually a team of five or six people can like [16:19] handle this product ad nauseum. Sometimes you have to bump it up. It's like, okay, this thing's about to go to production. There's all these other things to do. The team now needs to go from 4 to 15 or something like that. It really depends on the product. But that's the general life cycle. And then you keep growing and scaling it. [16:34] That is fascinating. So just to understand, [16:37] 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. [16:46] Interesting, okay. And then you find a design partner for them to work with to figure out what exactly needs to be built. [16:52] And is it idea pick one design partner, or you try to encourage a few? [16:56] Usually it's one. So there's a designer, right? So we have a designer. Oh, a design partner, meaning a designer, not a company that is their partner in design. Oh, no, no, no, no. Like literally somebody who knows Rippling's products, knows our component library, knows all that stuff and is skilled and [17:15] doing you know ux and you know interaction and visual design got okay designer okay cool [17:21] And then they basically, with maybe a couple of engineers, just that's the team that initiates a new product line. [17:27] and then launches it, and then as it [17:30] scales that maybe grows the team, maybe not. [17:33] Yep, that's right. And like, you know, every, you know, it's pretty ad hoc, but every couple of weeks or 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 eye for like, oh, man, if I were using this as a.

[17:49] admin, you know, a small company or an admin at 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. [18:03] This reminds me, you're also, I hear, not a big fan of MVPs. [18:07] that you like building... [18:09] products to further point. Is that true? 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 MVPs. I think MVPs have their place. They're extremely useful, particularly if you're literally at a zero to one company that's never done anything before and you don't have clear market validation. I think in our case specifically for Rippling, a minimum viable product would do a disservice [18:34] like to both our customers and to like the very team that was building it. And the reason I believe that is that when you design a minimum viable product, you're optimizing for speed. 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. [19:04] product creativity, but worse, [19:08] it leads to building the wrong thing technically. [19:12] 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?

[19:19] healthcare hospital administration case where 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... [19:31] six months, 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 going to look like for you to approach it? But also, [19:58] understand what it would mean to have 10,000 people [20:02] globally around the world with this like ridiculously hard use case what's the model that would support that [20:09] And let's make sure that as we're doing the technical and product design for this thing, that it accommodates that view, even if we're not going to support it in the first version. Even if we make the product decision to say, look, we actually don't need to handle that case right now. [20:23] 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? [20:31] Sure. [20:32] Yeah, but does it save you time in the long run? Absolutely. Right. And so, um, [20:37] So that's our approach. Is there an example that comes to mind of a product you build at Rippling or Coinbase of just like it could have been this [20:44] really simple MVP and then it ended up being like, "No, we did the right thing by building it further along the spectrum."

[20:49] Yeah, so I think a great example of this at Rippling is our global payroll product. [20:55] We could have said, "Hey, look, we just need to support this one country." [21:00] We need to support the UK, let's say. So we're going to copy all of our US stuff [21:08] Just replicate it and change all the things to be UK-like. That would have been the fastest thing to do to dramatically oversimplify. But that's not what we did. [21:17] What we did is we said, look, we need to launch with six countries. [21:20] And these are six super different countries that we want to look at. And they're going to have different requirements from 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. And there's lots of downstream implications for that. But what it means... [21:41] is that now our global payroll system, adding a country, [21:45] is it's not easy but it's a lot easier than it would have been if you had to like 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 [22:00] payroll platform. And then the 20% is country specific. And most of that specificity can be had a lot by engineers, who are very, very expensive to change things that are local specific, but instead can be configured by [22:15] 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. I've heard you describe this kind of idea as you encourage teams to design for the most complex systems.

[22:31] Use case first. Is that kind of the instruction you give these teams? [22:34] 100% many times. And so it's one of these things that like until you're here, it's a really difficult thing to kind of. [22:41] grok because a so counterculture to what like the background that most people have come from it's like no no no don't think about all those things just like zoom in on this on this one case use it as a wedge and then grow from there 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 [23:04] 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 cultures to do things the hard way and the right way. [23:24] And an element of that is there's this concept that I've heard that Rippling is this compound startup. [23:29] What does that term mean? And then how does that approach impact the way you build product and organize teams and all the things you were just talking about of MVPs and... [23:38] you know, build new products. [23:40] The idea of a compound startup for us is that we're basically a lot of businesses. [23:45] that all work together, right? Like if you think about the products we offer, we have payroll. [23:51] Well, there's entire companies built just on payroll. [23:54] Insurance and benefits, entire companies, that's their 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, 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, you know, before he founded the company was like, actually,

[24:17] the result you get that when you have that [24:19] is that there's all this data that gets replicated and copied, and it's 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 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 [24:46] benefit. [24:47] from being built on top of one platform. The activation energy for that is extremely high, right? So before my time at the company, you know, Parker, Prasanna, 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. But having done it, [25:06] right we then had that platform and we could continue to build like new verticals and new startups [25:12] right on top of that foundation. [25:15] This touches on something that comes up a number of times in this podcast, which is the importance of differentiation. [25:20] And it feels like this is the differentiator for rippling. It's not going to be just a better... [25:25] one of these vertical solutions, the main differentiators. We're going to do it all [25:29] and everything's going to be so much better because it's all in one platform. Is that kind of where the original idea... [25:34] or is there a different way to think about that? [25:37] Yeah, 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...

[25:53] Unless you start with that assumption of everything being in a single system of record, there's a bunch of other things you can't do. [25:59] You can't build out a, I don't know, a permissioning system that looks at the various attributes across all these products. You now suddenly have to do an integration and 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?" [26:16] Most products you can't do that. Most products you find some system of truth [26:20] export everybody's name and email address in a spreadsheet. [26:24] have another email address or another name, maybe an employee ID of 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 with Rippling, [26:37] it's always correct. 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. And that's a very, very simple example of something that you can only do if you start with, to come back to an earlier point, solve the most complex use case first. Solve the fact that this data all needs to be in the same place. [26:56] And so our ability to kind of differentiate [26:59] 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. [27:09] What would you say is... [27:11] One of the most unique things about Rippling's culture that maybe you haven't mentioned yet. [27:15] I would say it's speed of execution. [27:18] I think in speed of decision making, it's the thing that [27:22] is probably the hardest to explain to people before they're here. Like it's hard to understand until you experience it. Like,

[27:29] Let's not schedule a meeting for next week or tomorrow or later today. [27:36] 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. [27:43] and we'll be done with the decision today. And like, sure, there are irreversible decisions you can't make that way. [27:47] But for the most part, we really value the tempo of decision-making and the speed of response. And [27:55] 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 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. [28:14] I'm reading Kevin Kelly's new book. I don't know if you've seen his new book. It's all these little tidbits of advice. [28:20] And one of his pieces of advice is that usually the best time to do something is right now. [28:25] And it feels like that resonates with the way you all think. [28:29] I'm curious just how you create that culture and ability to make decisions fast. Is it purely top-down founder? [28:36] 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? [28:43] 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 like have a company that makes decisions quickly. And so he models this constantly, right? In Slack and 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 is something that kind of everybody promulgates.

[29:13] take it in [29:14] Right. 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're 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. [29:44] or give me 30 minutes to look something up, and 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. [29:55] You talked about quarterly planning and you're saying that there's like, here's the timelines [29:59] 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. [30:06] That's right. And so and so and it's it's shocking to people when we actually move on that haven't been here yet. It's like, no, no, that date passed. You don't get 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 just means it's like gets reinforced on sort of its own out of its own gravity. Do you have. [30:35] values like internal values that you've kind of outlined 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 COO 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 of Rippling leadership principles.

[31:05] 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. [31:35] 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. 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 [32:05] anytime, and you'll only hear from companies that you want to hear from. Check out lenny'sjobs.com slash talent. [32:13] For... [32:14] 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 [32:21] What piece of advice would you give someone for helping them do this at their company? [32:27] I think it's really context dependent, but I think it starts with whoever is in the role of making the top level product decisions, of them being, one, extremely clear.

[32:40] about what those priorities are, and more importantly, extremely clear about what all the priorities aren't. [32:45] 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. But secondly, for that person to go all the way to ground on it. [32:59] We have one of the leadership principles is go and see. 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... [33:11] this top-level communication is insufficient. [33:15] 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, [33:22] 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. OK, I definitely want to spend my 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. [33:51] people continuing to ask questions and going to the end of what's possible. A recent story was IO talking about building the cash card and going to the warehouse and watching the printings of the cards and things like that. Yeah. I guess, first of all, do you have a sense of where that came from and why that ended up being so important? [34:08] 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?

[34:16] In the early days of our global efforts, when we were first trying to figure out what global payroll was, it was really tempting to say, "Oh, well, we're going to go into the UK and that's going to be relatively similar to what we're doing in the US." But our head of payroll went in and said, "Actually, [34:32] Here are the ways in which 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. [34:41] for how we think about learning about each of these countries and going into them and having a fulsome experience. And that then backs into things like, well, every country does tax filings. [34:55] every country does them slightly differently. [34:58] but how are we going to build a tax filing system that's going to allow us [35:02] to satisfy the needs of every country [35:05] in which we're going to run payroll. [35:07] And it was only through that very early on deep look at how one country was actually operating [35:15] 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. [35:30] And so the leader of that team basically just went and studied [35:33] the tax [35:34] laws of each year. [35:36] That's right, like went all the way to ground. It's like, okay, let's go and open up the big old, I mean, it's like online these days, a big old tax book. Or when you're in the United States, you have to go look at Ohio or Pennsylvania, which have all these little local city or county-based taxes. And it's incredibly instructive to look at just a few of those and think, wow.

[35:58] How do I think about configuring these change unannounced? Like some city administrator or the city legislature, whatever they call them, right? [36:08] 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 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... [36:30] 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... [36:47] tax expert on the team. And I imagine many leaders would be like, go figure this out and tell me. [36:52] And I think what you're saying is you go do that and learn, become the world expert. That's right. [36:56] That's right. You go do it. You go learn. And then we can make the case for hiring the tax expert. [37:01] Right. Which we do have, by the way, now. Right. Like that's 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 what they're that's what they're they love and that's what they do. But that doesn't make them necessarily a great product thinker. [37:18] So the person with the product thing has to get into those same weeds first to really understand it. [37:23] Do you give any guidance on just like how much time to spend on all that stuff versus like, you know, the regular day to day?

[37:29] of say a product leader on a team. It takes a lot of time to become a world expert on attacks. [37:34] 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 it 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 that it 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 you know communicating with you know the engineering team and like writing documents or whatever but [38:04] document if you don't know what you're talking about. Right. 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. [38:15] We expect a single leader [38:18] to be able to know the full scope of the product. In fact, great product leaders can, in fact, do that because they have this native curiosity and interest and ability to absorb a lot of stuff. And it's a lot of fun because now I have a group of people around me who are all really good at what they do and really understand what they do. And that's kind of just an amazing, amazing place to be. I'm looking at this list and I just want to keep asking questions about it.

[38:48] It reminds me of Amazon has the same principle, I believe, which is [38:50] Leaders are right a lot. [38:52] Yeah. [38:53] 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... [38:59] follow often and comes up a lot. I mean, this is one of my favorite ones because I think for particularly for a product org, right? Because product leaders are, [39:09] have to be right most of the time because their decisions reflect 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 like an ambiguous situation with incomplete information and like a complex decision space. [39:37] and can look at that and listen to everybody and read whatever they need to read and say, [39:41] This is where we need to go. [39:43] And even if everyone else is like, I don't know, that feels wrong for this reason, this reason, if they have like... [39:48] the confidence to make that call. And then a year later, when you look back on it, for them to have been right, [39:55] That's extremely valuable. And it's one of these things that's really hard to test for. [40:00] Right. You can you can get it by like talking with people and and asking, hey, was this person like usually right in retrospect? 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. [40:17] You can't really learn it. Right. Either 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 that we really value.

[40:28] Awesome. [40:29] Shifting a little bit. [40:31] I know you all are going through this global expansion. We talked about this a little bit. And so just a few questions along those lines, because a lot of companies start, you know, one country, most companies do. [40:40] And then they decide, let's expand to new markets. [40:42] So I guess first question is just how do you decide which markets to go after and specifically where to start first? [40:50] And then just prioritizing the list of markets. What's kind of your algorithm for that? [40:55] So it starts with an assumption that we're going to have to be everywhere, ultimately. Right? That... [41:00] You don't actually have to build native global payroll in every country in the world. It doesn't make sense to do that in 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 HRS anywhere in the world. The decision for us, we were fortunate when we made that decision to have quite a few customers, like thousands and thousands of customers, and so we knew not only where their US employees were, [41:25] But by virtue of being an employee system, we actually knew where they had other employees. And 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 countries X, Y, and Z. And we just like, [41:43] listed those out in raw numerical order. And then we looked at, okay, how hard is it to build in these countries and how valuable is it to build in these countries? What is the strategic value of building in [41:55] the UK or Canada or Germany or India or wherever. And then we had a discussion on where is there a risk? Where is this hard? Where is there a long pull? In what countries does it take a long time to get approval or whatever?

[42:09] And we just stack ranked them. 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 dived into countries and learned more, you know, we rejigger things like a little bit. [42:24] But for the most part, like that same basic list we started with is still like [42:28] you know, mostly right. [42:29] Okay, and then the other question a lot of [42:31] founders always struggle with is when is the time to start expanding internationally because, you know, there's pros and cons. [42:37] Do you have a sense of what convinced you all to start going international? [42:41] 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. [42:54] People in the UK really, really care if there is a you in color, right? 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 that 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. [43:24] going to be around in 10 years because companies [43:27] we're becoming global. [43:29] And then [43:30] COVID happened and companies became global much faster. [43:35] It stopped being the province of 100-person companies plus, and started filtering down into very, very small companies. It just became commonplace for small companies to be multi-country. And so that very much...

[43:47] accelerated kind of our timetable. 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 [44:03] fire under the thing. [44:06] 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? [44:15] I think the thing that was most surprising to me [44:19] the first time I did this back at Guidewire in the aughts, and remains the most surprising thing to most people every time I do this again, is that [44:29] Every country is unique. [44:31] you can't just take your US-based approach. [44:36] and 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, [44:44] 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 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 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 so that is consistently the thing that I think is

[45:14] respect, 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. And, and so it takes just a lot of energy to, [45:29] to kind of overcome that organizationally. Makes tons of sense. [45:34] 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 I'm curious just to hear your perspective on [45:45] why you're maybe not a fan of frameworks, and then also just like how you crystallize. [45:48] processes and concepts for your team if you're not just like, "Hey, here's a framework you should use." [45:54] Look, I think frameworks are very helpful. I'm not exactly anti-framework, but I am anti-process as a substitution for deep product thinking. So I like to have just enough process to create a frame so that the right decisions can happen and no more. I think there's a danger, especially as companies scale, that you end up saying, well, if only we categorize everything correctly in Jira, we will be able to make really good prioritization decisions. [46:24] Okay. [46:24] Sure, extremely helpful to have clear categorization and things like Jira's, and have 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 have a way to build it really efficiently. [46:39] So I think the right answer, the right amount of process for any given team, or the right framework for any team, is really just

[46:45] dependent on their specific life cycle. So you won't see me saying like, "Oh, we need to use this Scrum thing or that Kanban thing or whatever 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." [47:02] to build the right thing as efficiently as possible. And I'm fine if those are different for different teams, [47:08] And the only place I care about unification is one, on the quarterly planning process, and two, like, [47:12] Everything does need, in fact, to be in JIRA, because otherwise you can't rationalize about what's actually getting done in that. [47:18] Is there a process or framework that you find is counterproductive, that you're just like, stay away from this thing? We've had a lot of trouble with it. Or... [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. So I think any framework sort of has its place, right place, right time. [47:39] I think there's danger any one time somebody dogmatically says, I think we should use process X, because that's almost never the right answer in my experience. I think there are places where that can differ. You start a company on the basis of process X, and everyone's bought into that process, and everyone understands it. I think that could be really, really great. And on the engineering side, I think this is hugely valuable. It's test-driven development, first line of code is going to be a test, not the actual thing. Fantastic, very supportive of all that. I think it's kind of different in the product world. [48:08] If you had to compare the way Coinbase builds product process-wise or just product development process-wise to Rippling, what would you say are the...

[48:15] 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 Coinbase run, 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. [48:41] right, at Coinbase. Here, [48:43] 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 discontinuously better than everything that's out there? And that like yields a different... [49:00] decision-making process. So for me, it's like the mental model is actually of how I approach those things are the same, but they just like [49:06] yield different results in the actual... [49:10] making of the software. What is that actual difference you find day to day? Is it timeline differences? Is it how quickly, I don't know, the way you structure, how far out you plan? What do you find is the concrete difference? [49:24] as a result. I think the difference is in the day-to-day velocity of decision-making, right? Because we can [49:33] Rippling, if you're on the device management team, [49:38] you know what you got to do. There's no ambiguity. You're not debating about whether Mac or Windows is going to exist in the future. There's none of that cognitive dissonance.

[49:51] We need to build this. [49:52] 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 kind of, [50:01] total velocity, I would say, is higher here, which is not to say people work harder or less hard at Coinbase. Coinbase was an amazingly fast environment. But it was also subject to the fact that 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. The reactivity to the environment and the crypto environment, what's going on, and the uncertainty of the regulatory environment, all that stuff. We got really, really, really good at handling those things really rapidly, which is something... [50:31] that we need to handle somewhat less, um, here. Sounds quite stressful. Uh, [50:35] at Coinbase. [50:38] Yeah, I mean, it was... [50:40] It was fun. Yes, it was stressful. I mean, every job I've ever had has been stressful, but in its own unique way. But all of that stress, I think, [50:50] 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? [50:57] But yeah, it's stressful. [51:00] And looking back, what a joy. Yeah. 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... [51:10] you know, forging these relationships and building these amazing products that, that I've been so lucky to be a part of. And, and so I have, you know, [51:17] Almost only good memories of the places I've been. That's what I find, too. You go through these hardships.

[51:23] 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 a startup. [51:32] Your life sucks for two years and [51:34] It doesn't work out on that. [51:36] There is a lot of upside and [51:38] Good memories to that, but it's less glorious. [51:41] Yeah, that's fair. [51:42] Though, I mean, the first company I was really at, kind of out of school, was a 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 new 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. Ultimately got kind of spun itself out and got acquired, which is great. [52:07] But it was this extraordinary set of people that I was so lucky to work with. And I loved all the time I spent there. And it was foundational to... [52:16] 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 [52:27] really exceptional, so I feel very lucky. That's a really good [52:31] point, actually, and I think I should correct even what I said, that even when things don't like [52:36] work out traditionally, those experiences end up being incredibly valuable in all these unexpected ways. [52:40] Yeah, 100%. [52:43] Okay. [52:43] So final topic. [52:45] I want to talk about hiring, hiring product managers and interviewing. [52:48] Yeah. 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 be focused on enough?

[53:00] I mean, I don't know that I have any particularly special insight here. I think there's a couple things that I do ask that maybe are more of an emphasis because it's rippling than not. But the first of those is when people are kind of going through our process, there's a part where they do this case study. And an important part of the case study is that it's like, [53:18] actually too complex for people to 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 in the interview, there's a lot of opportunities, or in the case study, there's a lot of opportunities. So just ask ad hoc questions. [53:32] Or to like [53:34] change one assumption and seeing how people react to that. [53:38] is really indicative of how deeply they understand [53:42] 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 times 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 questions that people ask, [54:12] in the job [54:14] Right. Like 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 OK. I don't expect the quality to be the same all the 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. 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 a pretty good candidate on my hands.

[54:44] really good question like that that comes to mind that you think back to and like, oh, wow. [54:47] That was great. [54:48] I remember about three years ago, I was interviewing a guy named Kyle Boston. [54:54] Kyle now runs our platform product organization. [55:00] 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, [55:08] And [55:09] you have this employee system of record thing underneath it. [55:13] Shouldn't we be thinking about how to create these various pillars of underlying platform technology, things like permissioning, all this stuff? And this was before we fully formalized the concept of our platform beyond the employee system of record. And I remember thinking, like, [55:31] Yes, yes we should. And that had entered our minds before, but the fact that somebody who had almost no context on the company, that's what was impressive about this question. It's like, man, you've been thinking about Rippling for a couple weeks while you're interviewing with a bunch of other companies or whatever. [55:46] 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 him to think through. And I think it touches on PMs need to be business leaders. And yeah. [56:02] Great questions are often about the business and the future of the business and how to make it run more efficiently and [56:08] There's like a product org element to it. [56:11] But I find that that's a really under... [56:13] I appreciate element of PM interviews, just like thinking about the bigger business, not just like the PM product.

[56:18] Yeah, for me, it's like two things. It's like thinking about the bigger business, right? And having the context like around, you know, whether it's like [56:24] 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, that 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 that you give product managers, not to give away what you're [56:54] example, [56:55] of a prompt that you've given in the past or you think is a good example of a type of prompt to give a product manager candidate. [57:01] In terms of a general kind of approach, I think a prompt... [57:05] should always reflect the actual business that they're going to come into. So our process overall is actually quite short. It's basically get in contact with us somehow. [57:17] eventually get connected with a hiring manager, have a conversation with them. [57:21] Then more or less you have a conversation with me, which is a product discussion. And then we have a case study. [57:26] which follows that. That's the whole process, modulo, other conversations around the edges. [57:32] The questions that matter are around 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, which is, uh, you know,

[57:49] Maybe it sounds very simple, but it's just like, "Hey, what questions do you have for me?" [57:55] We actually do that before we do the product discussion. And that's an incredibly important question because it is, again, indicative of these things 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 at that second discussion, it doesn't have to be perfect or anything. [58:25] looking for about what they like doing and not doing just through those questions. [58:30] For PMs that are maybe in their early career that are listening to this, [58:33] What advice would you give them to help them accelerate and advance their career most in the early part of their career? [58:40] Career. Be humble. [58:42] being a product person means that like by definition you're living in a world where like [58:49] 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, 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 [59:14] that that humility is one of the biggest differentiators in early career product leaders, who are able to let go of how awesome they were in school or in their first job or whatever. I mean, I had to do this. And realize the job is always hard.

[59:32] And the job is always about discovery every single day. And if you can maintain that curiosity and elasticity of thought and creativity and like coming solutions, it could be awesome. But if you close yourself off to that and think you always have the right answer, then there's 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. [59:56] yeah, willing to look at new information and say, my mental model is adjusted by that or I was wrong. [1:00:02] 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. [1:00:07] Everyone's wrong sometimes. I mean, be right a lot, but everyone's wrong sometimes. And being able to be in an environment where you can just say, "Yep, I was wrong. Here's the way in which I was wrong. Let's move on," is incredibly powerful. Final question. You've brought up Parker a number of times, and something that is clear about him is that he's very product-minded. [1:00:26] He has a lot of strong opinions about what products should be. [1:00:28] And, yeah, [1:00:29] as a product leader with a founder like that is often a challenging place to be. [1:00:33] similar to [1:00:35] being the first PM at a startup. [1:00:36] and the founder has strong opinions about product. [1:00:38] My question is just what have you learned about being successful as a product leader? [1:00:43] with a founder that has very strong opinions about what their product should be. [1:00:47] Yeah, it's a great question. So I think you've got to be adaptable, right? It's like any other relationship, right? You have to understand 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. I think fundamentally, you need to make sure that person is willing to be challenged, right? So I've seen product leaders or CEOs who are kind of unwilling to be challenged, and I wouldn't be

[1:01:17] 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... [1:01:27] it's not even a ceo but whatever a manager's idiosyncrasies are you have to find a way to like [1:01:33] work with those. I think that adaptability, I like being a moldable puzzle piece where I can just kind of fit in. I think that's actually one of my core skills. And so that's worked out for me. And Parker and I, before I started, started developing a deep foundation of respect, which is extremely important to building that. And over the years, it's just gotten deeper and deeper. And [1:01:58] You know, we don't always agree, but like when we don't, we can have a totally reasonable discussion about it. And and that's what makes it fun. [1:02:06] 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. [1:02:15] Yeah. [1:02:16] Seems like an important attribute for being in a place you're in. [1:02:19] Well, with that, we've reached our very exciting lightning round. [1:02:22] 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? [1:02:31] 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. And I also love the culture series by Ian Banks, which is just like super fun, far future sort of universe that I that I've really enjoyed. What's a favorite recent movie or TV show?

[1:03:01] Watched The Last of Us. I was an avid fan of the game and I thought they did a really nice adaptation. [1:03:08] favorite, like, I guess recent movie. It's not that recent, but I really liked Tenet, you know, which I thought was a... 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... [1:03:27] 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 could it. That 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. And then Tennant feels like, I was just thinking, it feels like a compound. [1:03:44] Movie. [1:03:45] Compound Startup as a movie. That movie is very complicated, too. [1:03:49] Yeah, that's why I enjoyed it. I like trying to figure out 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 you'd like to ask? You already maybe answered this, but anything else come to mind? I think I did. No, my favorite one is like, what questions do you have for me? Great. What are some favorite products you've recently discovered that you love?

[1:04:19] 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. I had to do like some really quick research into my new favorite pair of headphones. And these Focal Bathys are like, [1:04:46] super nice. I'm a bit of an audiophile. I like to listen to classical music and ambient stuff, so we need a lot of dynamic range and noise cancellation. These have been great so far. [1:04:57] Okay, so what is it? What are they called? [1:04:59] Focal, I think it's Bathys, 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 it when you see it. Okay. We will link to that in the show notes and maybe I'll get one. What's something relatively minor you've changed in the way that you built product? [1:05:16] that has had a lot of impact on your team's ability to execute. Maybe the most recent innovation at Rippling was the introduction of what I'm calling imperatives. These things that whether they come bottom up or top down are things that [1:05:29] 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 a line and say, these are the ones everyone has to do, has created a lot more focus and clarity than we had before. [1:05:48] 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. So each team still is building their own priorities, but they have to factor in this set.

[1:06:04] How many of those do you usually have? This is awesome. I like this tip. [1:06:07] It depends on what level of granularity you want to talk about them at. Maybe 10. It's a lot. We're going through, between globalization and large improvements to the platform and a bunch of other large companies, all these things, it creates a bunch of things that just have to be cross-teamed simultaneously. I think it's a pretty natural part of a company's evolution, and we're just in that part of the cycle. Awesome. [1:06:34] Final question. [1:06:35] What's a question I should have asked you that I didn't ask you? [1:06:38] I guess... [1:06:39] What do I do with my kids, maybe? I have two kids. [1:06:42] They're nine and six. What do I do with my kids? Um, [1:06:46] My son, I'm a big board gamer, and while I didn't push it on him, my son... [1:06:50] he will play board games morning to night. And so we play a lot of European strategy games together. And my daughter's now getting old enough that she's getting into them too. [1:07:02] We just finished as a family playing Pandemic Legacy, and the reward tomorrow night is we get to start playing Gloomhaven. [1:07:09] 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. Jeremy, we covered a lot of topics. I feel like this is a compound issue. [1:07:22] podcast episode. [1:07:23] And thank you for spending time with me. Thanks for being here. Two final questions. [1:07:28] Where can folks find you 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, 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.

[1:07:46] What's the best way to explore those roles and apply it? [1:07:49] The website has by far the best channel. It gets to this right recruiter who will tell me about it right away. Great. So Rippling.com and there's probably a site for careers. There's a career site on there that's pretty easy to find. We'll link to that in the show notes. [1:08:01] Jeremy, thank you again for being here. [1:08:04] Thanks so much for having me. This was a lot of fun. Bye, everyone.