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

Jeremy Henrickson is Rippling’s SVP of Product, responsible for scaling their product and design team across three continents. Previously, as Chief Product Officer at Coinbase, he oversaw 10x growth of the product and engineering organization and transformed a scrappy startup into a global cryptocurrency platform with tens of millions of users. He began his career at Apple in the 1990s and holds a BS and MS in computer science from Stanford. In today’s episode, we discuss: • Strategies for sustaining focus and momentum at scale • The case against MVPs • The problem with frameworks • “Compound startups” and how this influences Rippling’s product development process • Advice for founders wanting to move faster • Why you don’t understand your product unless you’re “in the weeds” • Hiring practices at Rippling and how young PMs can build fruitful careers — Brought to you by Miro—A collaborative visual platform where your best work comes to life | Mixpanel—Product analytics that everyone can trust, use, and afford | Lenny’s Job Board—Hire the best product people. Find the best product gigs Find the transcript at: https://www.lennysnewsletter.com/p/moving-fast-and-navigating-uncertainty Where to find Jeremy Henrickson: • Twitter: https://twitter.com/jeremyhenricks • LinkedIn: https://www.linkedin.com/in/jeremyhenrickson/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Jeremy’s background (03:24) What it was like leading product teams at Coinbase during the crypto boom (05:25) How Jeremy kept teams focused and the biggest challenges he faced at Coinbase (07:35) Advice for going through intense periods at work (08:52) Maintaining velocity at scale (12:07) An example of small teams with clear missions (14:29) A model for building products (18:03) Jeremy’s thoughts on MVPs (minimum viable products) (22:26) Designing for the most complex use case first (23:17) What a compound startup is and how it works at Rippling (27:09) Rippling’s unique culture of fast decision-making (28:14) Rippling’s leadership values (32:13) Advice for cultivating fast-decision-making teams (33:44) How deep-level thinking and working on the ground helped Rippling expand to other countries (38:42) Why product leaders need to be right (40:42) How Rippling decided where to expand to first (42:29) The case for expanding internationally before you think you’re ready (45:32) Why Jeremy isn’t a huge fan of frameworks (48:08) The differences between building product at Rippling and Coinbase (52:49) How Jeremy hires PMs at Rippling (58:29) Advice for junior PMs (1:00:19) Lessons from working with a founder who has strong opinions about what the product should be (1:02:15) Lightning round Referenced: • Coinbase: https://www.coinbase.com/ • Ethereum: https://ethereum.org/en/ • Parker Conrad on Twitter: https://twitter.com/parkerconrad • Rippling: https://www.rippling.com/ • Excellent Advice for Living: Wisdom I Wish I’d Known Earlier: https://www.amazon.com/Excellent-Advice-Living-Wisdom-Earlier/dp/0593654528 • Matt MacInnis on Twitter: https://twitter.com/stanine • Rippling’s leadership principles: https://www.rippling.com/life • Airbnb cereal story: https://www.cnbc.com/2023/04/18/airbnb-ceo-says-he-wooed-first-investors-with-boxes-of-cereal.html • Guidewire: https://www.guidewire.com/ • Jira: https://www.atlassian.com/software/jira • Kyle Boston on Twitter: https://twitter.com/KyleB • Quicksilver (book one of the Baroque Cycle series:) https://www.amazon.com/Quicksilver-Baroque-Cycle-Vol-1/dp/0060593083/r • Consider Phlebas (book 1 of The Culture series): https://www.amazon.com/Consider-Phlebas-Culture-Iain-Banks/dp/031600538X/ • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • The Game on Paramount+: https://www.paramountplus.com/shows/the-game-2021/ • Tenet: https://www.imdb.com/title/tt6723592/ • Corsair H60 CPU cooler: https://www.amazon.com/CORSAIR-Hydro-Liquid-Cooler-Radiator/dp/B00A0HZMGA • Focal Bathys headphones: https://www.amazon.com/Focal-Over-Ear-Bluetooth-Headphones-Cancelation/dp/B0B93YKQT3 • Pandemic: https://www.amazon.com/Z-Man-Games-ZM7101-Pandemic/dp/B00A2HD40E • Gloomhaven: https://www.amazon.com/Cephalofair-Games-CPH0201-Gloomhaven/dp/B01LZXVN4P Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  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 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 by going through that detailed exercise.

• 0:31Lenny Rachitsky?

  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 the product and design teams. 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 of 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

• 1:13Lenny Rachitsky?

  can be so detrimental to your success, why you may want to avoid MVPs and instead design for the most complex use cases first, 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 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/lenny. With the help of the Miro team, I created a super cool Miro board with two of my own favorite templates, my one pager template and my managing up template, that you can plug and play and start using immediately with your team. I've also

• 1:58Lenny Rachitsky?

  embedded a handful of my favorite templates that other people have published in the Miroverse. When you get to the board, you can also leave suggestions for the podcast, answer a question that I have for you, and generally just play around to get a sense of how it all works. Miro is a killer tool for brainstorming with your team, laying out your strategy, sharing user research findings, capturing ideas, giving feedback on wireframes, and generally just collaborating with your colleagues. I actually used Miro to collaborate with the Miro team on creating my own board, and it was super fun and super easy. Go check it out at miro.com/leni. That's M-I-R-O dot com slash leni. This episode is brought to you by Mixpanel.

• 2:40Lenny Rachitsky?

  Get deep insights into what your users are doing at every stage of the funnel at a fair price that scales as you grow. Mixpanel gives you quick answers about your users from awareness to acquisition through retention. And by capturing website activity, ad data, and multi-touch attribution right in Mixpanel, you can improve every aspect of the full user funnel. Powered by first-party behavioral data instead of third-party cookies, Mixpanel is built to be more powerful and easier to use than Google Analytics. Explore plans for teams of every size and see what Mixpanel can do for you at mixpanel.com/friends/leni. And while you're at it, they're also hiring. So check it out at mixpanel.com/friends/leni.

• 3:27Lenny Rachitsky?

  Jeremy, welcome to the podcast.

• 3:30Speaker 00

  Thank you so much for having me. I'm excited to be here.

• 3:32Lenny Rachitsky?

  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.

• 3:44Speaker 00

  Yeah, super happy to be here.

• 3:46Lenny Rachitsky?

  So I want to start with your time at Coinbase where you were Chief Product Officer. And you were Chief Product Officer during maybe the craziest time in the crypto markets. It was, I think, 2016, 2018, when I was looking at the Bitcoin prices, and it was like, it went from like $1,000 to $20,000, I think, in a matter of months. So I'm curious, what was that experience like? And in particular, what was it like leading a product team through that experience?

• 4:10Speaker 00

  The strongest memories for me are during like 2017, where crypto, which had kind of been at its nadir in like early 2016, and kind of slowly started climbing out, just kind of took off and became a real thing in the public consciousness. And Coinbase, which at the time had an exchange just like on-ramp and off-ramp from fiat to crypto and back, experienced over the course of 2017, 40x growth.

• 4:37Speaker 00

  In in usage.

• 4:39Lenny Rachitsky?

  That's like a dream come true for for a lot of people.

• 4:41Speaker 00

  It's it. No, I mean, it it was. It was both a dream and a nightmare. 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 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. And so a lot of Saturday mornings, there's like some new like like thing would break on the edges of the system. And we need to kind of get in there and 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 at the right time.

• 5:25Lenny Rachitsky?

  OK, 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 rich all over the place in crypto. Things are breaking all the time. Like, how did you maintain focus on on your team?

• 5:43Speaker 00

  Well, the first thing is you don't talk about people getting rich. It's like it's a 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 Barton 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 we need to move. And so security was always like the number, the number one thing. And then 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, and like resolving that.

• 6:25Speaker 00

  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 to have, you know, everything from a user experience to kind of the the deep backend of the product? That would actually work for them.

• 6:41Lenny Rachitsky?

  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?

• 6:50Speaker 00

  I think the biggest challenge was that in crypto, 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 because lots is going, 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 that you're all, that you're all shooting toward. And like, while there may still be differing points of views and debates that happen on the margins, like 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.

• 7:32Lenny Rachitsky?

  Maybe just a last question there.

• 7:34Speaker 00

  Sure.

• 7:34Lenny Rachitsky?

  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, working like incredibly long hours. But then you look back at those times and end up being some of those important meaningful periods of your career.

• 7:52Lenny Rachitsky?

  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, uh, here's maybe the silver lining of being in a period like that.

• 8:03Speaker 00

  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, 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, 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, or five years from now, when we look back on this, we realize, wow. You know, we, A, we did something amazing with that time.

• 8:45Speaker 00

  And B, we, 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.

• 8:52Lenny Rachitsky?

  Before our chat, I asked you what people ask you for advice most around. And you said that it's, 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?

• 9:12Speaker 00

  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 like small teams with clear missions. Right? You know, if there's 300 people trying to work on one thing, like the just sheer like communication challenges done by our 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 whole heartedly and minimize like horizontal communication, I think is the first thing.

• 9:55Speaker 00

  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, easy to use and 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. 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.

• 10:39Speaker 00

  The third thing, just from a leadership point of view is like diving deep, 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 what you, 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, 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

• 11:22Speaker 00

  team is like perhaps doing something that's like zero to one 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 that part of the job as much and B, maybe they're not as good at it. So I think you have to 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, 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.

• 12:07Lenny Rachitsky?

  Okay, let me dig into a couple of these. These are really great.

• 12:10Speaker 00

  Yeah, please.

• 12:11Lenny Rachitsky?

  So with the small teams with clear missions, is there an example of that at Rippling or Coinbase? Where that was like a really good example of this being true?

• 12:20Speaker 00

  One example is maybe three years ago, when I, when I was just starting at the company, we decided that we needed to build a time in 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, really talented systems engineer who's actually capable of doing kind of product thinking and have Parker, CEO, also spend time on it. And you start there, right? And Satish brought a few people on with him and those four people over the course of maybe nine months or so, built a time in attendance product. It was the only thing they were doing. They didn't

• 13:04Speaker 00

  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 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.

• 13:24Lenny Rachitsky?

  How much of that was Parker being on the team, helping them unblock everything versus being very small and focused?

• 13:30Speaker 00

  I think it was mostly small and focused. Like, obviously, Parker can do things and unblock them in the way that only a CEO can, and that helps. The thing is that Rippling, we've now replicated that a dozen times. 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 this pattern of having these small groups be able to do things, and then being able to go to those people, 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. All of those things can happen just at a much greater tempo than if you're trying to go three layers down into the org and do things.

• 14:12Speaker 00

  I think that's the other, maybe, 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.

• 14:29Lenny Rachitsky?

  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 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 new product here. What is that model, roughly?

• 14:45Speaker 00

  Yeah, so the model's quite simple. In the vast majority of cases, we realize we need to build something. And we have 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 time and attendance is an example. That's a well-known thing in the industry. There's whole companies that do only that. 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 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, come into Rippling, spend a few months

• 15:26Speaker 00

  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 it, 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 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. And we dog food our stuff really

• 16:11Speaker 00

  heavily. And then it grows from there. And then sometimes when you launch one of these products, get close to launch, realize, hey, actually, a team of five or six people can like, kind of handle this product. And I was saying, 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 needs now needs to go from four 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.

• 16:34Lenny Rachitsky?

  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?

• 16:45Speaker 00

  Both.

• 16:46Lenny Rachitsky?

  Interesting. 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?

• 16:56Speaker 00

  Usually it's one. Like, so there's a designer, right? So we have, you know, a design.

• 17:00Lenny Rachitsky?

  Oh, a design partner, meaning a designer, not a company that is like their partner in design?

• 17:06Speaker 00

  Oh, no, no, no, no. Like, literally, somebody who, who, who knows Rippling's products, knows like our component library, knows all of that stuff, and is skilled in like, doing, you know, UX and, you know, interaction and visual design.

• 17:19Lenny Rachitsky?

  Got it. 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, it maybe grows the team, maybe not?

• 17:33Speaker 00

  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 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?

• 18:03Lenny Rachitsky?

  This reminds me, you're also, I hear, not a big fan of MVPs, that you like building products to further, to a further point. Is that, is that true? And then if so, how do you, how do you think about the initial version of a product?

• 18:16Speaker 00

  First of all, I don't want to knock on MVPs. I think MVPs 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. 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

• 18:57Speaker 00

  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 or hospital administration case where like, you know, it's mission critical and 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, nine months, a year, and you'll have dozens or hundreds of assumptions built on top of those. And

• 19:38Speaker 00

  it's extremely difficult to unwind those decisions once you've built them into the product. And, 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 does a product going to 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? Right? 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, right? Even if we make like the product decision to say like, look, we actually don't need to handle that case right now.

• 20:23Speaker 00

  You still build the product in a way that's not going to, 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, um, so that's our approach.

• 20:38Lenny Rachitsky?

  Is there an example that comes to mind of product you built at Rippling or Coinbase of just like, it could have been this really simple MVP and then ended up being like, no, we did the right thing by building it further along the spectrum?

• 20:49Speaker 00

  Yeah. So I think a great example of this at Rippling is our global payroll product. Right? We could have said, hey, look, um, we just need to support this one country. Right? We need to support, uh, whatever, the UK, let's say. So we're going to copy all of our US stuff, like just replicate it and like change all the things to be UK like. 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, that we want to like 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.

• 21:33Speaker 00

  And we're going to make a system that works for those countries. 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 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 payroll platform. And then like the 20% is like country specific. And most of that specificity can be handled not 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

• 22:18Speaker 00

  get the right documents into the system. And all of that stuff can be handled by, by, by the system, which allows us to move much faster sort of going forward.

• 22:26Lenny Rachitsky?

  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?

• 22:34Speaker 00

  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 grok because A, it's 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. 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, the balance of those two things. Right?

• 23:17Lenny Rachitsky?

  So when I think about Rippling, I think of you got kind of the culture is to do things the hard way and the, the right way. And an element of that is there's this concept that I've heard that Rippling is this compound startup.

• 23:30Lenny Rachitsky?

  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, about MVPs and, you know, build new products?

• 23:40Speaker 00

  The idea of a compound startup for us is that we're basically a lot of businesses that all work together. Right? Like, if you think about, about the products we offer, we have payroll. Well, there's entire companies built just on payroll. Insurance and benefits, entire companies, that's an entire life. In fact, like a fragment of benefits is the entire life cycle of the whole company. You know, our IT products, device management, 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, the result you get that when you have that is that there's all this data that gets replicated and copied. It

• 24:22Speaker 00

  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 kinds of underlying capabilities. So the idea of a compound startup is like, all of these different businesses. Benefit from being built on top of one platform. The activation energy for that is extremely high. Right. So before my 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.

• 25:05Speaker 00

  But having done it, right, we then had that platform and we could continue to build like new verticals and new startups. Right. On, on top of that, um, on top of that foundation.

• 25:16Lenny Rachitsky?

  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 just a better, one of these vertical solutions. The, 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, is that kind of where the original idea came from? Or is there a different way to think about that?

• 25:37Speaker 00

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

• 26:17Speaker 00

  Most products, you find some system of truth, export everybody's name and email address in a spreadsheet. You know, have another email address or another name, maybe an employee ID of like who that person reports to, and upload that to another system, which by the way, is immediately out of date because organizational structures change all the time. Whereas with Rippling, it's always correct, right? We are the system of record. So all of our products, they're like, hey, who's that person's manager? And the system immediately knows, right? And that's a very, very simple example of something that, that you can only do if you start with like solving, 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?

• 27:00Speaker 00

  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.

• 27:09Lenny Rachitsky?

  What would you say is one of the most unique things about Rippling's culture that maybe you haven't mentioned yet?

• 27:15Speaker 00

  I would say it's fundamentally the 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. 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 you 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.

• 27:54Speaker 00

  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 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.

• 28:14Lenny Rachitsky?

  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 it 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, 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?

• 28:43Speaker 00

  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 and 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. But also I think there's a number of things we've done to sort of like bake it in. 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

• 29:24Speaker 00

  of room in the way that we expect people to know their domains, especially in product, right? And product, you're, you don't own like a 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, look something up. And like, I can tell you what we need to do about that. And so all of those things in combination just yield an environment in which these decisions happen very quickly.

• 29:55Lenny Rachitsky?

  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 gonna move on.

• 30:06Speaker 00

  That's right. And so, and so, and it's, it's shocking to people when we actually move on, right? That haven't been here yet. It's like, no, no, that date passed. You don't, 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. 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 that sort of its own, out of its own gravity.

• 30:34Lenny Rachitsky?

  Do you have 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?

• 30:42Speaker 00

  No, we actually, I find them quite valuable. And actually, our COO, Matt MacInnis, 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 the specific URL, but on Rippling, there's a search of Rippling leadership principles. You know, there they are. And they are really true to the culture of the company. The way we came up with them was to us, you know, a couple of years ago, to introspect and to what the, 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.

• 31:23Lenny Rachitsky?

  Are you hiring? Or on the flip side, are you looking for a new opportunity? Well, either way, check out lennysjobs.com/talent. If you're a hiring manager, you can sign up and get access to hundreds of hand-curated people who are open to new opportunities. Thousands of people apply to join this collective, and I personally review and accept just about 10% of them. 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 specific companies. You can also leave anytime, and you'll only hear from companies that you want to hear

• 32:08Lenny Rachitsky?

  from. Check out lennysjobs.com/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 piece of advice would you give someone for helping them do this at their company?

• 32:26Speaker 00

  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, 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? There are so many things that could be important, or people can make the case for being important or whatever, that are fundamentally distracting from the core mission of getting something done. But secondly, for that person to go all the way to ground on it, right? We have one of the leadership principles is go and see, right? 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.

• 33:09Speaker 00

  Because inevitably, this top-level communication is insufficient.

• 33:15Speaker 00

  To get to like the detail of like what matters and doesn't matter. You don't have to do that everywhere, but if you do it in enough places, what it does is it creates a clear expectation of that kind of clarity 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.

• 33:43Lenny Rachitsky?

  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.

• 34:03Speaker 00

  Yeah.

• 34:04Lenny Rachitsky?

  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 do that and that leading to something really important?

• 34:16Speaker 00

  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 US. But our kind of head of payroll went in and said 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?

• 35:01Speaker 00

  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.

• 35:30Lenny Rachitsky?

  And so the leader of that team basically just went and studied the tax laws of each country.

• 35:35Speaker 00

  Yeah, 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 the old tax book and look like, it's like, or when you're in the United States, like, you have to go look at Ohio or Pennsylvania, which have all these, like, little, like, local, like, city or county-based taxes. And it's 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 ground and looked at how these things are actually, actually

• 36:18Speaker 00

  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 it and understanding it firsthand, you don't really understand what your product needs to do.

• 36:41Lenny Rachitsky?

  And I think an important element of this that's between the lines maybe is, don't delegate this to someone. Like, you may have a tax expert on the team, and I imagine many leaders would be like, go, go figure this out and tell me. And I think what you're saying is, you go do that and learn, become the world expert.

• 36:55Speaker 00

  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 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. Right. So the person with the product thing has to, has to get into those same weeds first to really understand it.

• 37:24Lenny Rachitsky?

  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 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, how do you think about it?

• 37:42Speaker 00

  I think it's an equilibrium, you know, if a job is 80 hours a week, it's like 40 of your hours. Like it's, 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, the other half of the job of, you know, communicating with, you know, the engineering team and like writing documents or whatever, but like, what's the point of writing a document if you don't know what you're talking about? 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. Right. We expect like a single leader, right, to be able to know like the full scope of the product. In fact, great product leaders can in fact do that because they like have this native

• 38:25Speaker 00

  curiosity and, and interest and like ability to absorb a lot of stuff. And, uh, and it makes, it's a lot of fun because now like I have a group of people around me who like are all like really good at what they do and really understand what they do. And that, that's kind of just an amazing, amazing place to be.

• 38:42Lenny Rachitsky?

  I'm looking at this list and I just want to keep asking questions about it. Uh, one of the

• 38:46Speaker 00

  Sure.

• 38:46Lenny Rachitsky?

  principles that I love is, and it reminds me of Amazon has the same principle, I believe, which is leaders are right a lot.

• 38:52Speaker 00

  Yeah.

• 38:53Lenny Rachitsky?

  Why do you find that to be important? I know you weren't necessarily designing all these principles, but I imagine that something that you guys follow often and comes up a lot.

• 39:01Speaker 00

  I mean, this is one of my favorite ones because I think for particularly for a product org, right? Because product leaders. 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 information with 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

• 39:46Speaker 00

  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, that's extremely valuable. And it's one of these things that like, it's really hard to test for, right? You can, you can get it by like talking with people and, and asking, hey, was this person like usually right in respect to people think about it? But like in the context of like a given company, just you have to take the time and see if those decisions are largely right. And it's the one value we have, it's like, you can't really learn it, right? Either, 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.

• 40:28Lenny Rachitsky?

  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 those lines, because a lot of companies start, you know, one country, most companies do, 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, your algorithm for that?

• 40:55Speaker 00

  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, 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. And so the decision for us, we were fortunate to, when we made that decision to have quite a few customers already, like thousands, thousands of customers. And so we knew not only where their kind of US employees were, but by virtue of being an employee system, we actually knew where they had other employees. And so it was quite easy for us to say, focusing on US-based companies, which is incomplete data, right?

• 41:35Speaker 00

  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 listed those out in raw numerical order. And then we kind of looked at, okay, how hard is it to build in these countries? And how valuable is it to build in these countries, right? Like, what is the strategic value of building in the UK or Canada or Germany or India or wherever? And then we had a discussion on like, where 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 stacked 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.

• 42:19Speaker 00

  And as we've dove, dived into 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.

• 42:29Lenny Rachitsky?

  Okay. And then the other question a lot of founders always struggle with is when is the time to start expanding internationally? Cause you know, there's pros and cons. Do you have a sense of what convinced you all to start going international?

• 42:41Speaker 00

  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 there, 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 U in color, right? Just as we care if there's not a U 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, 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.

• 43:23Speaker 00

  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 timetable. And then you saw, you know, other people noticed 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, under the thing.

• 44:06Lenny Rachitsky?

  What have you found to be most surprising about expanding internationally to be successful in, in expansion for folks that are maybe starting down this road of like, oh shoot, we should think about that?

• 44:15Speaker 00

  I think the thing that was most surprising to me, the first time I did this back at Godwire 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 US-based approach and like drop it into another country. Other countries find it insulting. It doesn't matter how much success you've had here. Everyone always believes rightly or wrongly that their local context is special and you have to respect that. And it comes down to like little things like there being a you and color or not. Or, you know, if you ever see a demo delivered to somebody in another country where they

• 44:58Speaker 00

  see like a detail screen about a person and then 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, that is consistently the thing that I think is most surprising to people is the degree to which that's true, which seems obvious in retrospect, right? If you took like German system or something and like demoed it in the United States with like poorly translated stuff, we would think it would suck too, right? And so, but it's not, it's really hard to adapt to that mindset. And, and so it takes just a lot of energy to, to kind of overcome that organizationally.

• 45:31Lenny Rachitsky?

  Makes tons of sense. I'm going to go in a different direction now. Frameworks. So I know that you're not a huge fan of frameworks. We were chatting about this before we started recording. And so 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, here's a framework you should use.

• 45:54Speaker 00

  Look, I think frameworks are very helpful, although 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. And I think there's a danger, especially as companies scale, that you end up saying, well, you know, if only we categorize, you know, everything correctly and JIRA like, you know, we will be able to make like really good prioritization decisions. I'm like, sure, extremely helpful to have clear categorization and things that yours and have like data and analysis and to be able to do all of that stuff. But what you really need to do is decide what's important to build. Right? And then like have a way to build it like really efficiently.

• 46:38Speaker 00

  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 lifecycle. So you won't see me saying like, oh, we need to use like this scrum thing or that combo thing or whatever, like the latest newest thing is. It's like, don't care about any of that. What I care is about something that's going to enable this team in this context, at this point in their lifecycle, to build the right thing as efficiently as possible. And I'm fine if those are different for different teams. And the only place I care about unification is one, on the quarterly planning process. And two, like, everything does need in fact to be in JIRA because otherwise you can't rationalize about what's actually getting done and not.

• 47:18Lenny Rachitsky?

  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. Or generally, it's like, let's just rethink everything ourselves.

• 47:30Speaker 00

  Um, no, I don't find one to be particul-- I don't, I haven't consistently found one to be particularly problematic. So I think any framework sort of has its place, right place, right time. I think there's, I think there's danger any one time that somebody like dogmatically says, I think we should use process X, because that's almost never the right answer in my, in my experience. I think, I think there are places where that can differ. Like you start a company like on the basis of process X and like everyone's bought into that process and everyone understands it. Um, I think that can be really, really great. And like, and on the engineering side, I think this is hugely valuable. It's like test-driven development, first line of code is going to be a test, not the actual thing. Like fantastic, very supportive of all that. I think it's kind of different in the product world.

• 48:08Lenny Rachitsky?

  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 bigger differences?

• 48:17Speaker 00

  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 around like having those debates and like getting 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, 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 decision-making process.

• 49:01Speaker 00

  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 the different results in the, in the actual making of the software.

• 49:11Lenny Rachitsky?

  What is that actual difference 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?

• 49:25Speaker 00

  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, if you're on the device management team, like, you know what you gotta do, right? There's no ambiguity, you're not debating about, you know, whether, you know, Mac or Windows is going to exist in the future, like, none of, there's none of that cognitive dissonance, right? There is, we need to build this, 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, but we need to basically get this done. And so, the, the kind of total velocity, I would say, is, is higher here, which does not say people work harder or less hard at Coinbase, like Coinbase was like an amazingly

• 50:09Speaker 00

  fast, like, environment, but it was also subject to the fact that, like, you just don't know what the crypto markets are going to do, and you have to be incredibly reactive to that. And so I think maybe that's the one thing, like, the reactivity to, like, the environment and the crypto environment, what's going on, and the, 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 here at Rippling.

• 50:33Lenny Rachitsky?

  Sounds quite stressful at Coinbase.

• 50:37Speaker 00

  Uh, yeah, I mean, it was, um, it was fun, like, I, stress, yes, it was stressful, I mean, every job I've ever had has been stressful, but in, in its own unique way, but all, 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, um, but yeah, it's stressful.

• 50:59Lenny Rachitsky?

  And looking back, what a joy.

• 51:01Speaker 00

  Yeah, no, they are very good memories. Like, I look back, I don't really, I remember the stress, but I don't, like, re-experience it, right? I, I remember, like, you know, forging these relationships and building these amazing products that, that I've been so lucky to be a part of, and, um, and so I have, you know, almost only good memories of the places I've been.

• 51:20Lenny Rachitsky?

  That's what I find, too. You go through these hardships, uh, 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 at a startup, you, your life sucks for two years and it doesn't work out in that. There is a lot of upside and good memories to that, but it's less glorious.

• 51:41Speaker 00

  Yeah, that's fair. 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, fundamentally, like, didn't work out. Ultimately, got 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,

• 52:24Speaker 00

  and then the people I had a chance to work with, was just really exceptional. So, I feel very lucky.

• 52:30Lenny Rachitsky?

  That's a really good point, actually. And I think I should correct even what I said, that even when things don't, like, work out traditionally, those experiences end up being incredibly valuable in all these unexpected ways.

• 52:41Speaker 00

  Yeah, 100%.

• 52:42Lenny Rachitsky?

  Yeah. Okay. So, final topic. I want to talk about hiring, hiring product managers and interviewing.

• 52:48Speaker 00

  Yeah.

• 52:49Lenny Rachitsky?

  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 as you know?

• 53:00Speaker 00

  I mean, I don't know that I have any, like, particularly special insight here. I think there's a couple of things that I do ask that maybe are more of an emphasis because it's rippling than not. But like, 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, actually too complex for people to, like, have all of the answers upfront. It's just like, the space of the problem is too large to do that. Which means that, like, in the interview, there's a lot of opportunities, or in the case 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.

• 53:42Speaker 00

  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 in assumption, they like blink a couple of 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 questions that people ask, which is indicative of number one, their like actual interest in the job. Right. Like people tend to ask better questions when they're like more excited about working at a place. And it's like done their research and are asking people about it. And also like the quality of those questions like can vary quite dramatically.

• 54:26Speaker 00

  And, and that's okay. I don't expect the 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 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 a pretty good candidate on my hands.

• 54:42Lenny Rachitsky?

  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.

• 54:48Speaker 00

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

• 55:33Speaker 00

  And you know, that had entered our minds before, but the fact that somebody which who had like almost no context on the company. Right. That, that's what was impressive about this question. It's like, man, even thinking about Rippling for like a couple of weeks while you're like 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, and his ability to kind of think through the sorts of things we need him to think through.

• 55:58Lenny Rachitsky?

  And I think it touches on PMs need to be business leaders and

• 56:02Speaker 00

  Yeah.

• 56:02Lenny Rachitsky?

  great questions are often about. The business and the future of the business and how to make it run more efficiently. And listen, you know, 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.

• 56:18Speaker 00

  Yeah, for me, it's like two things. It's like thinking about the bigger business, right? And having, having the context like around, you know, whether it's like revenue questions or strategy questions, but also like the detailed questions. Right? 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, that this isn't a simple business. Like it's really hard, it's really complex. And the ability to kind of, to have these insights, help them think through those details is really cool.

• 56:48Lenny Rachitsky?

  You talked about this prompt they, you give product managers, not to give away what you actually ask these days, but is there an example of a prompt that you've given in the past, or you think is like a good example of a type of prompt to give a product manager candidate?

• 57:01Speaker 00

  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, so when we do like, so our process overall is, is actually quite short. It's basically, you know, getting 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 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.

• 57:43Speaker 00

  And the second thing is there's always a part of my interview, which is, which is, uh, maybe sounds very simple, but it's just like, hey, what questions do you have for me?

• 57:55Speaker 00

  Right. We actually do that before we do the product discussion. And that's an incredibly important question because it is, again, indicative of like these things that people have thought through or not thought through, or kind of the depth 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 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, you learn a lot about how people think about product, about, you know, what they're looking for, about, you know, what they like doing and not doing, just through those questions.

• 58:30Lenny Rachitsky?

  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 in the early part of their career?

• 58:41Speaker 00

  Be humble. Being a product person means that like by definition, you're living in a world where like no one knows the right answer yet, because if somebody did, they would have already built it. Right? And so having like, no matter how smart you are, and 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 in early career product leaders who sort of are, you know, able to let go of like how awesome they were in school or in their first job or whatever. I mean, I had to do this.

• 59:27Speaker 00

  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 coming solutions, it can be awesome. But if you close yourself off to that and think you always have the right answer, then there's like no hope.

• 59:49Lenny Rachitsky?

  This touches on another principle that I still have sitting on my screen here, which is that great leaders change their minds a lot, or just change their minds.

• 59:56Speaker 00

  Yeah, willing to look at new information and say, my mental model is adjusted by that, or I was wrong. 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 and being in be able to be in 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 is incredibly powerful.

• 1:00:19Lenny Rachitsky?

  Final question, you've brought up Parker a number of times and something that is clear about him is that he's a very product minded founder. 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 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 their product should be?

• 1:00:47Speaker 00

  Yeah, no, it's a great, it's a great question. So I think you've got to be adaptable, right? Like, it's like any other relationship, right? You have to understand like what the nature of that relationship is, where that person's going to care, where you're going to care, the ways in which you can challenge each other. 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. And I wouldn't be able to work with those people.

• 1:01:17Speaker 00

  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, and it's not even a 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 worked, that's worked out for me. And, you know, Parker and I, before I started, you know, started developing like a deep foundation of respect, which is like extremely important to like building that. And like, over the years, it's just gotten deeper and deeper.

• 1:01:56Speaker 00

  And, you know, we don't always agree, but like when we don't, we can have a totally reasonable discussion about it. And, and that's what makes it fun.

• 1:02:06Lenny Rachitsky?

  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 adaptable. I think we share that.

• 1:02:14Speaker 00

  That's excellent.

• 1:02:15Lenny Rachitsky?

  Yeah, seems like an important attribute for being in a place you're in. Well, with that, we've reached our very exciting lightning round. I've got six questions for you if you're ready.

• 1:02:24Speaker 00

  All right. I'm ready. Hit me.

• 1:02:27Lenny Rachitsky?

  Here we go. What are two or three books that you've recommended most to other people?

• 1:02:31Speaker 00

  Well, first is like my favorite series of books ever, which is The Baroque Cycle by Neil Stephenson. It's a nine-volume epic, or 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've really enjoyed.

• 1:02:58Lenny Rachitsky?

  What's a favorite recent movie or TV show?

• 1:03:01Speaker 00

  Watched The Last of Us. You know, was an avid fan of the game and I thought they did a really, really nice adaptation. Favorite, like, I guess, recent movie, it's not that recent, but I really liked Tenet. Yeah, 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.

• 1:03:22Lenny Rachitsky?

  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 gonna drink some tea right here.

• 1:03:29Speaker 00

  Okay, fair enough. I'll try. I've only got water. Normally I got tea, but water didn't.

• 1:03:33Lenny Rachitsky?

  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. And then Tenet feels like, I was just thinking, it feels like a compound movie. Compound startup as a movie. That movie is very complicated, too.

• 1:03:49Speaker 00

  Yeah, I enjoyed it. I like, I like trying to like, figure out like, the multi-timeline chart in my head as the movie progresses.

• 1:03:56Lenny Rachitsky?

  Puzzle piece within you, trying to find all the puzzle pieces.

• 1:03:59Speaker 00

  Yeah, for sure.

• 1:04:00Lenny Rachitsky?

  What is a favorite, any of you question you'd like to ask? You already maybe answered this, but anything else come to mind?

• 1:04:06Speaker 00

  I think I did. No, my favorite one is like, what questions do you have for me? By far.

• 1:04:09Lenny Rachitsky?

  Great. What are some favorite products you've recently discovered that you love?

• 1:04:14Speaker 00

  I guess I'll just mention. I don't think as far as I call these favorite products, but there's two that come to mind. My wife's computer broke the other day and I realized it was the CPU cooler that went bad. And the Corsair H60 CPU cooler was like super easy to use and really adaptable to lots of other boards. I thought that was great. My other favorite product is the one I'm wearing in my ears right now, which my first pair of nice headphones I ever bought died last week, late last week. I had to do like some really quick research into my new favorite pair of headphones and these focal bathys are like super nice. I'm a bit of an audiophile. I like to listen like classical music and ambient stuff. So we need a lot of dynamic range and these and you know, noise cancellation and these have been like great so far.

• 1:04:57Lenny Rachitsky?

  Okay. So what is it? What are they called?

• 1:04:59Speaker 00

  Focal, I think it's bathys, B A T H Y S.

• 1:05:02Lenny Rachitsky?

  Okay. And is there a specific model or there's like that one?

• 1:05:06Speaker 00

  That's it.

• 1:05:06Lenny Rachitsky?

  Okay.

• 1:05:07Speaker 00

  You'll, you'll, you'll know when you see it.

• 1:05:09Lenny Rachitsky?

  Okay. We will link to them 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? That has had a lot of impact on your team's ability to execute.

• 1:05:20Speaker 00

  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, to kind of force rank that list of things, draw a line and say, these are the ones. Everyone has to do has created a lot more focus and clarity than, than we had before.

• 1:05:48Lenny Rachitsky?

  So imperatives are essentially like, here's the priorities for the next, say, quarter, six months here.

• 1:05:52Speaker 00

  The, these, here are the priorities for everybody. Now integrate that into your own team's priorities, right? So, so each team like still is building like their own priorities, but like have to factor in like this set.

• 1:06:04Lenny Rachitsky?

  How many of those do you usually have? This is awesome. I like this tip.

• 1:06:08Speaker 00

  It, it, it depends. Like 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, we're going through like between like globalization and like large improvements of the platform and like a bunch of other, you know, you know, large companies, all these things. It creates a bunch of things that just have to be cross-team simultaneously. I think it's a pretty natural part of a company's evolution and we're just in that part of the cycle. So.

• 1:06:33Lenny Rachitsky?

  Awesome. Final question. What's a question I should have asked you that I didn't ask you?

• 1:06:38Speaker 00

  I guess, what do I do with my kids, maybe? I have two kids. They're nine and six. What do I do with my kids?

• 1:06:46Speaker 00

  My son, I'm a big board gamer. And while I didn't push it on him, my son, he will play board games, you know, morning to night. And so we play a lot of like European like strategy games together. And my daughter's now getting old enough that she's getting into them too. And so we just finished as a family playing Pandemic Legacy and the reward tomorrow night is we get to start playing Gloomhaven. So that's gonna be fun.

• 1:07:11Lenny Rachitsky?

  I don't know, either game sounds very hard and complicated.

• 1:07:15Speaker 00

  They're fun. They're fun.

• 1:07:17Lenny Rachitsky?

  Amazing. Jeremy, we covered a lot of topics. I feel like this is a compound podcast episode. And so, thank you for spending time with me. Thanks for being here. Two final questions. Where can folks find you online if they want to reach out, learn more? And how can listeners be useful to you?

• 1:07:32Speaker 00

  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.

• 1:07:46Lenny Rachitsky?

  What's the best way to explore those roles and apply?

• 1:07:49Speaker 00

  The website has by far the best channel. It gets to the right recruiter who will tell me about it right away.

• 1:07:55Lenny Rachitsky?

  Great. So, rippling.com and there's probably a site for careers.

• 1:07:58Speaker 00

  There's a career site on there that you're pretty easy to find.

• 1:08:00Lenny Rachitsky?

  We'll link to that in the show notes. Jeremy, thank you again for being here.

• 1:08:04Speaker 00

  Thanks so much for having me. This was a lot of fun.

• 1:08:06Lenny Rachitsky?

  Bye, everyone.

• 1:08:08Lenny Rachitsky?

  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. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.