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Jeremy Henrickson

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2023-06-04
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2023-06-04
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  1. Awesome. LinkedIn is the easiest way online. And, you know, what I've been talking about today sounds interesting to you. We're definitely hiring senior entrepreneurial PMs. And so if those leadership principles on our website look interesting, I'd love to hear from you.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. I guess, what do I do with my kids maybe? I have two kids. What do you do with their kids and six? What do I do with my kids? My son, I'm a big board gamer. And while I didn't push it on him, my son, he will play board games 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. 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 going to be fun.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. It depends on what level of granularity you want to talk about them at. Like maybe 10, it's a lot. We're going through between globalization and large improvements of the platform and a bunch of other 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. Here are the priorities for everybody. And 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. 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 everybody across the entire product 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 we could choose do hundreds of things at once, like being able to force rank that list of things, draw lines. These are the ones everyone has to do has created a lot more focus and clarity than we had before.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. I guess I'll just mention Colley's favorite products, but there's two that come to mind my wife's computer broke the other day and I realized it was the CPU cooler that went bad. And the Corsair H60 CPU cooler was like super easy to use and really adaptable to lots of other boards. I thought that was great. My other favorite product is when I'm wearing my ears right now, which my first pair of nice headphones I ever bought died last week, late last week. It had to do like some really quick research into my new favorite pair of headphones and these focal bathies are super nice. I'm a bit of an audio file. I like to listen to like classical music and ambient stuff, so we need a lot of dynamic range and these and noise cancellation and these have been like great so far.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. Watch The Last of Us. I 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 like Tennet, which I thought was impressed with their ability to kind of go there and make that movie. And I just really enjoyed it, like end-to-end.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. 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-volume nine book epic, depending how you want to look at it. But it's about the time just before and 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

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. 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 we don't always agree. But when we don't, we can have a totally reasonable discussion about it. And that's what makes it fun.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. Yeah, no, 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 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, you know, I've seen product leaders or CEOs who are like kind of unwilling to be challenged. And I wouldn't be able to work with those people. But 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 whatever, and not even a CEO, but whatever a manager's idiosyncrasies are, you have to find a way to work with those. And I think 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Willing to look at new information and say, my mental model is adjusted by that, or I was wrong. 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, everyone's wrong sometimes. I mean, be right a lot, but everyone's wrong sometimes, right? And be able to be 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. And realize the job is always hard. And the job is always about discovery every single day. And if you can maintain that curiosity and elasticity of thought and creativity and lightcoming solutions 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

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

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. 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 that they're thinking or their interest and engagement in the role. And like at that second discussion, it doesn't have to be like perfect or anything. 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 on the fly, like generating them, you learn a lot about how people think about product, about what they're looking for, about what they like doing and not doing just through those questions.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. In terms of a general kind of approach, I think a prompt should always reflect the actual business that they're going to kind of come into, right? So when we do, like, so our process overall is actually quite short. It's basically getting contact with us somehow, eventually 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. And the second thing is there's always a part of my interview, which is maybe sounds very simple, but it's just like, hey, what questions do you have for me?

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. Yeah, for me, it's like two things. It's like thinking about the bigger business and having the context around whether it's like revenue questions or strategy questions, but also the detailed questions. 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. It's really hard. It's really complex. And the ability to kind of have these insights help them think through those details is really cool.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. 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 immediately gave me a bunch of confidence in his ability to kind of think through the sorts of things we need him to think through.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. I remember about three years ago, I was interviewing a guy named Kyle Boston. And Kyle is 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 employee system of record thing underneath it, shouldn't we be thinking about like how to create these various pillars of kind of underlying platform technology things like permissioning all this stuff? And this was before we fully formalized the concept of our platform beyond the kind of employee system of record. And I remember thinking like, yes, yes, we should. And that had entered our minds before, but the fact that somebody who had like almost no context on the company, right? That's what was impressive about this question. It's like, man, even thinking about rippling for like a couple weeks while you're like.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. Get like really flummocked. And obviously, for our environment, that former is like really, really important to us. I think the other thing that really matters to me is 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 like done their research and are asking people about it. And also like the quality of those questions can vary quite dramatically. 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 pretty good candidate on my hands.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. 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 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 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 to just like ask ad hoc questions or to change one assumption and seeing how people react to that is really indicative of how deeply they understand a new problem or how quickly or how mentally agile they are. And some people are extremely good at that. Like here in Assumption, I like blink a couple times. They're like, oh, well, that has like these 400 implications, right? And they just start rattling them off. And some people.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. I ever did. And so even though that effort and like, you know, pay off in the traditional set, like the value of the learnings I had there and then the people I had a chance to work with was just really exceptional. So feel very lucky

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. Yeah, that's fair. Though, I mean, the first company I was really at kind of out of school is a company called Reactivity back in Internet One Era. And we were trying to figure out how does this internet thing work? How do we start companies on the basis of these new technologies? How do we help other companies build stuff and figure it out? And that company fundamentally didn't work out. Ultimately, spun itself out and got acquired, which is great. But 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

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. Yeah. They are very good memories. Like I look back, I don't really remember the stress, but I don't like re-experience it, right? I remember foraging these relationships and building these amazing products that I've been so lucky to be a part of. And so I have almost only good memories of the places I've been.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. Yeah, I mean, it was fun. Yes, 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, is in the shape of a problem that's in the context of a problem that's really interesting. I mean, that's why I stayed at these places, right? And so, but yeah, it's stressful.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. 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 that we need to handle somewhat less hearably.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. I think the difference is in the day to day velocity of 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 got to do, right? There's no ambiguity. You're not debating about whether Mac or Windows is going to exist in the future. None of that cognitive dissonance, right? We need to build this. It's hard to figure out how we need to build this, right? Because there's all these different things that we could leverage, but we need to basically get this done. And so the kind of total velocity, I would say, is higher here, which does not say people work harder or less hard at Columbia. Columbia was like an amazingly fast 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. I think the differences are largely born of the different domains. 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 Coimbase where I'm like having those debates and like getting to a decision and disagreeing and committing and then from an execution point of view being able to move fast, like that was the trick, right, at Coinbase. Here we know the things that we need to build at a high level. And the trick is how do we really differentiate it on the basis of 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 yields a different decision making process. So for me, it's like the mental model is actually of how I approach those things with the same, but they just like yield different results in the actual making of the software.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. No, I don't find one to be particular. I haven't consistently found one to be particularly problematic. I think any framework sort of has its place, right place, right time. 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. Like you start a company on the basis of process X and everyone's bought into that process and everyone understands it. I think that can be really, really great. And on the engineering side, I think this is hugely valuable. It's like test driven development, first line of code is going to be a test, not the actual thing, like fantastic, very supportive of all that. But I think it's kind of different in the product world.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. Context at this point in their life cycle to build the right thing as efficiently as possible. And I'm fine if those are different for different teams. And the only place I care about unification is one 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  30. Look, I think frameworks are very helpful, so I'm not exactly anti framework, but I am anti process as a substitution for deep product thinking. Right. So I like to have just enough process to create a frame, right? So the right decisions can happen and like 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, like we will be able to make really good prioritization decisions. I'm like, sure, extremely helpful to have clear categorization and things in JIRAs and have 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. And so I think the right answer, the right amount of process for any given team is 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 this scrum thing or that Kanban 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  31. I think the thing that was most surprising to me 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 every country is unique? You can't just take your US-based approach 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, that their local context is special and you have to respect that. And it comes down to little things like there being a you in color or not. You know, if you ever see a demo delivered to somebody in another country where they see like a detail screen about a person and it includes a social security number, it's like you immediately lose credibility. It doesn't matter how good all the rest of your stuff is. And so I think 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 a 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  32. 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 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 fire under the thing.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  33. 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 it's harder than everyone, if they've never done it before, it's harder than you think it is. It's more specialized than you think it is. People in the UK really, really care if there is a you in color, right? Just as we care, if there's not a you in color, right? There's like all of these subtle lessons that 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. In our case, it was always something we knew we had to do. In fact, we have a very clear thesis that companies that aren't global, particularly in payroll, but also in kind of insurance and benefits and IT, if you're not global, you're just not going to be around in 10 years because companies were becoming global

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  34. And how valuable is it to build in these countries? 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 hard? Where's there a long pull? Where does this like, in what countries does it take a long time to get approval or whatever? And we just stack ranked them. And then we revisited that decision, like the early decisions that we made on exactly which countries, like we have subsequently reordered those over time. And as we've dove dived into countries and learned more, we rejigger things like a little bit. But for the most part, that same basic list we started with is still mostly right.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  35. So it starts with this assumption that we're going to have to be everywhere ultimately that 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 HRIS anywhere in the world. And so the decision for us, we were fortunate to, or when we made that decision to have quite a few customers already, like thousands, thousands of customers. And so we knew not only where they're kind of US employees were, but by virtue of being an employee system work, we actually knew where they had other employees. And so it was quite easy for us to say focusing on U.S.-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 listed those out in raw numerical order. And then we kind of looked at, okay, how hard is it to build in these countries?

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  36. Asking, hey, was this person like usually right and retrospect? People think about it. But in the context of a given company, see if those decisions are largely right. And it's the one value we have. It's like, you can't really learn it. Either you're really, really good at making those kinds of decisions or you're not, right? It's a very peculiar skill that we really value.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  37. I mean, this is one of my favorite ones because I think particularly for a product org, right? Because product leaders Have to be right most of the time because their decisions reflect 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 incomplete information and a complex decision space and can like look at that and listen to everybody and read whatever they need to read and say, this is where we need to go. And like even if everyone else is like, I don't know, that feels wrong for this reason, this reason, if they have the confidence to 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 it's really hard to test for, right? You can get it by talking with people and

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  38. What's the point of writing a document if you don't know what you're talking about? Right. 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 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 makes, 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  39. I think it's an equally, you know, if a job is 80 hours a week, it's like 40 of your hours. I think that. That you can't really understand a product unless you've gone there, right? And yes, it takes time. And you're right. You can't just ignore the other half of the job of communicating.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  40. 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, which we do have, by the way now, right? 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 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 get into those same weeds first to really understand it.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  41. How do I think about configuring these change on announced, right? Some city administrator 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 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 in different ways, right? It might be a technical thing. It might be a design thing. It might be a compliance or regulatory or governmental thing, but whatever it is, that detail always exists. And unless you're getting down there and seeing and understanding it firsthand, you don't really understand what your product needs to do.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  42. Right, like went all the way, like when all the way to ground, it's like, okay, let's go and open up the big old, like, I mean, it's like online these days with the big old textbook and look like it's like, or you're in the United States, like 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 like, wow.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  43. Every country does them slightly differently. But how are we going to build a tax filing system that's going to allow us to satisfy the needs of every country in which we're going to run payroll? And it was only through that very early on, like deep look at how one country was actually operating and then doing the same thing with the next country, that 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  44. In the early days of our kind of 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 kind of head of payroll went in and said, actually, 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, 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  45. There are so many things that could be important, or people can make the case for being important, or whatever, that are fundamentally distracting from the core mission of getting something done. But secondly, for that person to go all the way to ground on it, we have one of the leadership principles is go and see, right? So to look at the thing and then like walk all the way to ground and like talk with the engineer who's like writing the code on the thing because inevitably this top level communication is insufficient to get to like the detail of like what matters and doesn't matter. 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  46. 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 about what those priorities are and more importantly extremely clear about what all the priorities aren't.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  47. No, actually, I find them quite valuable. And actually, our COO, Matt McGuinness, who joined the company about a year before I did, he has been the one to really drive this. And you go to, I can't remember this specific URL, but on Rippling, there's a sort of rippling leadership principles. There they are. And they are really true to the culture of the company. The way we came up with them was to us a couple years ago to introspect and to what actually made people successful at the company, like who's successful, why are they successful, why do they enjoy being here? Or alternatively, the opposite, right? Like why people not worked out? Why do some people not enjoy it here? And those are the things that are differentiating. And those are the things that we wrote down.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  48. Right. And so, and so, and 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 make everybody react to the fact that you didn't operate quickly enough. And it's not a hostile thing, right? It's just people just have to get used to it. It's a deep cultural principle. And the fact that everyone stands behind it just means

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  49. 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.

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source

  50. Obviously, a huge piece of this is like Parker himself, right? It's an attribute of his personality. He likes making decisions quickly, and it's also a deliberate strategic decision on his part to like have a company that makes decisions quickly. And so he models this constantly, right? in Slack, in conversations in person in every way possible. And there's an expectation kind of throughout the company, if you kind of look at our leadership principles, like this ability to make decisions quickly is something that kind of everybody promulgates. 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 even do like say quarterly planning and the fact that there's this timeline for decision making that doesn't leave like, you know, a lot of room in the way that we expect people to know their domains, especially in product, right? In product, you don't own like little feature. You own like your product and you're expected to be the world's foremost expert in it. And if you are, what that means is like in

    2023-06-04 · Lenny's Podcast · Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase) · IDENTIFIED FROM THE TRANSCRIPT · source