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

Jeremy Henrickson (00:00:00):
It's very, very tempting to float up here as a leader and say, "Hey, you take that hill over there. You guys do this over here." When in fact, where you really learn where the challenges are, or the problems or the successes is by just being there with the people in the trenches on one of the things, whichever one seems hardest or most complicated. And so I try to do that as often as I can, and I found that I always learn a lot by going through that detailed exercise.

Lenny (00:00:32):
Welcome to Lenny's Podcast, for 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 10 x growth of the product and engineering organizations and helped scale Coinbase during one of the craziest times in the crypto markets. In our conversation, Jeremy shares his lessons about maintaining velocity at scale, creating a culture of fast decision-making, the importance of product leaders going deep on a problem, and becoming world experts at their domain. What to look for in product managers you're interviewing, why relying on frameworks can be so detrimental to your success, why you may want to avoid MVPs and instead designed for the most complex use cases first, and tons more. Enjoy this episode with Jeremy Henrickson after a short word from our sponsors.

(00:01:27):
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's all about and how we 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 embedded a handful of my favorite templates that other people have published in the Miro verse. 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.

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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/lenny. That's miro.com/lenny. This episode is brought to you by Mixpanel. 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, add 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/lenny. And while you're at it, they're also hiring. So check it out at mixpanel.com/friends/lenny. Jeremy, welcome to the podcast.

Jeremy Henrickson (00:03:30):
Thank you so much for having me. I'm excited to be here.

Lenny (00:03:32):
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.

Jeremy Henrickson (00:03:45):
Yeah, super happy to be here.

Lenny (00:03:46):
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 a $1000 to $20,000 I think in a matter of months. So I'm curious, what was that experience like, and in particular, what was like leading a product team through that experience?

Jeremy Henrickson (00:04:11):
The strongest memories for me are during 2017 where crypto, which had kind of been at its nadir in early 2016 and 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 40 x growth in usage.

Lenny (00:04:39):
That's like a dream come true for a lot of people.

Jeremy Henrickson (00:04:42):
No, I mean it was both a dream and a nightmare and I was incredibly lucky to be working on it with a team of people that I could really trust and could stand shoulder-to-shoulder within the trenches. And it was a lot of learning about how you can rapidly scale systems over time and people like to trade crypto on Saturday mornings, so a lot of Saturday mornings just some new thing would break on the edges of the system and we need to get in there and work on it. And so it was just a lot of really incredible lessons about who you choose to work with and focus and making sure you have the right people in the room at the right time.

Lenny (00:05:25):
Okay. So let's actually unpack a couple of those. So focus is really interesting and something people always talk about, but hard to actually do. I guess how did you keep the team focused? I imagine just everyone's getting rich all over the place in crypto.

Jeremy Henrickson (00:05:39):
Huh.

Lenny (00:05:39):
Things are breaking all the time, like how did you maintain focus on your team?

Jeremy Henrickson (00:05:43):
Well, the first thing is you don't talk about people getting rich. It's a very technical, you talk about like its customers, it's their money, and number one, it had to be secure. So there's a guy named Philip Barton, a friend of mine now, and he is just this amazing security leader at Coinbase, and he was able to always put these decisions that we were making extremely quickly in context and say, "Look, these are the kinds of decisions we can make and still have it be secure no matter how fast we need to move." And so security was always the number one thing. And then the second thing is focusing on both the kind of immediate nature of the issue. Hey, site is down or whatever, and resolving that, but also trying to set those in a context of where we need to go over the next six months. What are we actually shooting for? What do we believe the volumes are going to be? What's it going to take to have everything from a user experience to the deep back end of the product that what would actually work for them?

Lenny (00:06:41):
What was maybe the biggest challenge as a product leader trying to keep people focused and everything on the rails as things were going 40 x?

Jeremy Henrickson (00:06:50):
I think the biggest challenge was that in crypto there's just so much uncertainty in general, simple questions like, is Ethereum going to be a thing, are the subject of debate. And no one actually at the time had an answer to that question. Lots of really strong opinions and so you have to be able to have those debates because lots is going on, but then you have to be able to come out of those conversations with a clear kind of company point of view that you're all shooting toward. And while there may still be differing points of views and debates that happen on the margins, you go full speed toward this answer until you decide to go full speed toward a different answer. And I thought we were pretty successful at that at Coinbase and it wasn't always easy.

Lenny (00:07:32):
Maybe just a last question there.

Jeremy Henrickson (00:07:34):
Sure.

Lenny (00:07:34):
Living through a time like that, a lot of people are going through these periods of just 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 most important meaningful periods of your career.

Jeremy Henrickson (00:07:50):
Mm-hmm.

Lenny (00:07:52):
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 here's maybe the silver lining of being in a period like that?

Jeremy Henrickson (00:08:03):
So it's hard, right? It wasn't always easy. I had a new daughter who had been born just a few months earlier, really tough to balance those things, but I've always loved the rate of learning. And so it is those experiences I feel that have most sort of accelerated my own personal growth and personal learnings because it's in the crucible of things being hard. And so I think when people are going through those times, it's nice to take a step back and talk with friends or whatever about what's really going on and setting it in the context of, hey, three, four or five years now from now when we look back on this, you realize, wow. A, we did something amazing with that time. And B, we learned a lot and we were able to take that with us into whatever we were doing next after that.

Lenny (00:08:52):
Before our chat, I'd asked you what people ask you for advice most around, and you said that people often ask you for advice on how to maintain velocity at scale, which is something every founder and product leader is always striving to do. And so what have you learned and what do you tell people about maintaining and maybe even improving velocity as you scale?

Jeremy Henrickson (00:09:12):
I think there's a lot of different answers here, and I think a lot of them are very specific to the nature of the business that someone's in, like different businesses can maintain velocity in different ways. I think there's kind of a universal truth that you want small teams with clear missions. Right? If there's 300 people trying to work on one thing, the just sheer communication challenges, Dunbar's number, all of those things come into play and it's really, really hard to act quickly. And so having smaller groups of people breaking down what is always a very, very large problem into sufficiently small bits that small groups can attack wholeheartedly and minimize horizontal communication, I think is the first thing. I think the second thing is that to the extent it's like a technology problem. The more you can bake into a clear platform, it reduces the decision-making complexity for everyone who's working on the domain part of the problem.

(00:10:09):
And so a clear like a platform with a clear interface [inaudible 00:10:12] easy to use in all the ways that both engineers and product people want it to be easy to use, simplifies the space in which people have to think about these problems. And that's not always easy. Platforms are not, you can't just write a platform and hope it's going to work for the products. It's very much an iterative thing, but the more one can invest in that and have the right kinds of people who are capable of doing that sort of both systems thinking and product thinking simultaneously, I think is really important. The third thing, just from a leadership point of view is diving deep. Right? It's very, very tempting to float up here as a leader and say, "Hey, you take that hill over there, you guys do this over here." When in fact where you really learn where the challenges are or the problems or the successes is by just being there with the people in the trenches on one of the things, whichever one seems hardest or most complicated.

(00:11:05):
And so I try to do that as often as I can. And I found that I always learn a lot by going through that detailed exercise. And I think the last thing is it's just making sure that teams have the right distribution of experience and seniority. Sometimes you get a team started and the team is perhaps doing something that's zero-to-one and they're amazing at all this zero-to-one stuff.

(00:11:28):
And then two or three years later, those same people are trying to scale the product to 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 [inaudible 00:11:40] constantly look at the team and make sure that a people are doing things that they love and if they're not like, Hey, we've tried this other thing instead and recalibrate the team and make sure the right kind of skill sets are there. And I found if you do all of those things and then have product leadership where we're saying this is what we need to do 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.

Lenny (00:12:07):
Okay, let me dig into a couple of these. These are really great.

Jeremy Henrickson (00:12:10):
[inaudible 00:12:10] please.

Lenny (00:12:12):
So with the small teams with clear missions, is there an example of that at Rippling or Coinbase where that was a really good example of this being true?

Jeremy Henrickson (00:12:20):
One example is maybe three years ago when I was just starting at the company, we decided that we needed to build a time and attendance product, lots of market demand for us and 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 and Sachit brought a few people on with him.

(00:12:56):
And those four people over the course of maybe nine months or so, built a time and attendance product. It was the only thing they were doing. They didn't have to worry about what was going on with our payroll product except to the extent they had to integrate with them a little bit. They didn't have to worry about what was going on with the benefits team or our IT products. They were monomaniacally focused on this one thing and then identifying the places where yes, you, there's connectivity to the rest of the suite, and that allowed them to move extremely quickly.

Lenny (00:13:24):
How much of that was Parker being on the team, helping them unblock everything versus being very small and focused?

Jeremy Henrickson (00:13:30):
I think it was mostly small and focused. Obviously, Parker can do things and unblock them in the way that only a CEO can and that helps. But the thing is at Rippling, like 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 have 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.

(00:14:05):
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. I think that's the other, maybe the key point here that everyone is exposed 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.

Lenny (00:14:29):
So let's talk about that model you just described. So what is that model? So this is how you approach new products, and I know within Rippling there's many, many products and features we're going to talk about this. And you're saying that you have kind of an approach to adding a new business unit essentially, or a new product feature.

Jeremy Henrickson (00:14:42):
Yeah.

Lenny (00:14:43):
What is that model roughly?

Jeremy Henrickson (00:14:45):
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, right? So we start there, we find a single engineer who is extremely entrepreneurial, understands what it means to operate at tempo, understands what it means to make decisions with low information, understands how to work very, very quickly with a design partner.

(00:15:22):
So we have a design partner and we say, "Look, come into Rippling, spend a few months getting to know the platform first of all. So go work on this other team, understand what's easy for them, what's hard for them, how the platform works, how other products have been built on top of this. Go talk with other people who founded products here and understand what their experience is so that you can learn from and iterate on it, get an opinion about your product, and then start building it."

(00:15:48):
And during this intervening time, they're also recruiting a team of usually 2, 3, 4 other engineers who kind of have that same zero-to-one mentality and they start building. And usually over the course of six to nine months, we can get a product from a blank sheet of paper to something that is launched or at least that we're using internally when we dogfood our stuff really heavily. And then it grows from there. And then sometimes when you launch one of these products, you get close to launch, you realize, hey, actually a team of five or six people can handle this product ad nauseam. 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 4 to 15 or something like that. Really depends on the product, but that's the general life cycle and then you keep growing and scaling it.

Lenny (00:16:34):
That is fascinating. So just so I understand, you find a founder type to 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?

Jeremy Henrickson (00:16:34):
Both.

Lenny (00:16:34):
Interesting.

Jeremy Henrickson (00:16:34):
Both.

Lenny (00:16:46):
Okay. And then you find a design partner for them to work with to figure out what exactly needs to be built. And is it idea pick one design partner or you try to encourage a few?

Jeremy Henrickson (00:16:57):
Usually, it's one. So there's a designer, so we have a design-

Lenny (00:17:00):
Oh, design partner, meaning a designer, not a company that is like their partner in design.

Jeremy Henrickson (00:17:06):
Oh, no, no, no. Literally, somebody who knows Rippling's products, knows our component library, knows all of that stuff and is skilled and doing UX and interaction and visual design.

Lenny (00:17:19):
Got it. Okay, design. 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.

Jeremy Henrickson (00:17:33):
Yep, that's right. And it's pretty ad hoc, but every couple of weeks or something like that, they're meeting with me or with Parker or whichever one of us is the DRI on it and giving feedback on the designs, having a critical life or like "Oh man, if I were using this as a admin, 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 throughout that cycle and trying to get the balance of speed and comprehensiveness, right.

Lenny (00:18:03):
This reminds me you're also, I hear not a big fan of MVPs that you building products to further point. Is that true? And then if so, how do you think about the initial version of a product?

Jeremy Henrickson (00:18:16):
First of all, I don't want to knock on MVPs. I think MVPs have their place extremely useful, particularly if you're literally the zero-to-one company that's never done anything before and you don't have clear market validation. I think in our case specifically for Rippling, a minimum viable product would do a disservice to both our customers and to the very team that was building it. And the reason I believe that is that when you design a minimum viable product, you're optimizing for speed. And in that set of optimizations, you are minimizing the deeper product thinking about what can fully differentiate our product based on not only existing kind of capabilities within our products and platform, but based on what it ought to do in the future.

(00:19:03):
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 healthcare hospital administration case where it's mission-critical life," then you're going to make a different set of as 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 100s of assumptions built on top of those.

(00:19:38):
And it's extremely difficult to unwind those decisions once you've built them into the product. And therefore we believe very deeply it's like, sure, understand those simple cases. Understand if you're a two-person company, you don't need all of these other things. And what is the product going to look like for you to approach it but also understand what it would mean to have 10,000 people globally around the world with this ridiculously hard use case? What's the model that would support that? And let's make sure that as we're doing the technical and product design for this thing, that it accommodates that view, even if we're not going to support it in the first version, even if we make the product decision to say, "Look, we actually don't need to handle that case right now." You still build the product in a way that's not going to prevent you from getting there in the future. And does that take a little more time? Sure, yeah. But does it save you time in the long run? Absolutely. Right. And so that's our approach.

Lenny (00:20:39):
Is there an example that comes to mind of a product you build at Rippling or Coinbase of just, 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.

Jeremy Henrickson (00:20:49):
Yeah. So I think a great example of this at Rippling is our global payroll product. We could have said, "Hey, look, we just need to support this one country. We need to support, whatever, the UK," let's say. So we're going to copy all of our US stuff, just replicate it and change all the things to be UK-like. That would've been the fastest thing to do to dramatically oversimplify, but that's not what we did. What we did is we said, look, we need to launch a six countries and these are six super different countries that we want to look at. And they're going to have different requirements from an HRIS standpoint, from an employer of record standpoint, from how you pay global contractors, from how payroll works, and we're going to make a system that works for those countries. And there's lots of downstream implications for that.

(00:21:39):
But what it means is that now our global payroll system, adding a country is, it's not easy, but it's a lot easier than it would've been if you had to continue to stamp out and replicate and then of course maintain all of these things that have very little underlying connectivity. And instead, what we have is 80% of the system is baked into our global payroll platform, and then the 20% is country-specific. And most of that specificity can be handled not by engineers who are very, very expensive to change things that are local specific, but instead can be configured by somebody that's in compliance, by somebody that's in legal that needs to get the right documents into the system. And all of that stuff can be handled by the system, which allows us to move much faster sort of going forward.

Lenny (00:22:27):
I've heard you describe this kind of idea as you encourage teams to design for the most complex use case first.

Jeremy Henrickson (00:22:27):
Yeah.

Lenny (00:22:32):
Is that kind of the instruction you give these teams?

Jeremy Henrickson (00:22:35):
100%, many times. And so it's one of these things that until you're here, it's a really difficult thing to kind of grok because A, it's so counterculture to what the background that most people have come from. It's like, no, no, no, don't think about all those things. Just zoom in 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 absorbing the culture to 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 simultaneously with doing this, we're like, "Hey, but we need to ship this as fast as possible." Right? And so you want to get the balance of those two things right.

Lenny (00:23:17):
So when I think about Rippling, I think of you got the culture is to do things the hard way and the right way. And an element of that is there's this concept that I've heard that Rippling is this compound startup? What does that term mean? And then how does that approach impact the way you build product and organize teams and all the things you were just talking about of MVPs and build new products?

Jeremy Henrickson (00:23:40):
The idea of a compound startup for us is that we're basically a lot of businesses that all work together. If you think about the products we offer, we have payroll, well, there's entire companies built just on payroll, insurance, and benefits, entire companies. That's our entire life. In fact, a fragment of benefits is the entire life cycle of a whole company. Our IT products, device management, and identity management, time and attendance, each of these things are industries into themselves with multi-billion dollar companies serving each of them. The insight Parker had before he founded the company was actually the result you get that when you have that is that there's all this data that gets replicated and copied and as 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.

(00:24:34):
And then you can build on top of that things like workflow and reporting and analytics and permissioning and all these kinds of underlying capabilities. So the idea of a compound startup is all of these different businesses benefit from being built on top of one platform. The activation energy for that is extremely high. So before my time at the company, Parker, Prasanna, the technical founder, and others, built all of the first versions of all these products and it was a minor miracle, they were able to do that. But having done it, we then had that platform and we could continue to build new verticals and new startups on top of that foundation.

Lenny (00:25:16):
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 like the main differentiators, we're going to do it all and everything's going to be so much better because it's all in one platform. Is that kind of where the original idea came from or is there a different way to think about that?

Jeremy Henrickson (00:25:38):
Yeah, I think that's right. So I mean, the fundamental contention is having a single system of record is better for many, many, many reasons, right? The most simple of which is there's a single source of truth and all of these other products can rely on it. But also, unless you start without assumption of everything being in a single system of record, there's a bunch of other things you can't do. You can't build out a, I don't know, a permissioning system that looks at the various attributes 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, build a product and say, who is this person's manager? Most products, you can't do that. Most products you find some system of truth, export everybody's name and email address and a spreadsheet, have another email address or another name, maybe an employee ID of who that person reports to and upload that to another system, which by the way is immediately out of date because organizational structures change all the time.

(00:26:35):
Whereas with Rippling, it's always correct. We are the system of record. So all of our products, they're like, "Hey, who's that person's manager." And the system immediately knows. And that's a very, very simple example of something that you can only do if you start with solve it to come back to an earlier point, like solve the most complex use case first, solve the fact that this data all needs to be in the same place. And so our ability to differentiate boils down to that one fundamental decision, which just allows us to do things that are literally impossible for any other company to do.

Lenny (00:27:09):
What would you say is one of the most unique things about Ripplings culture that maybe you haven't mentioned yet?

Jeremy Henrickson (00:27:15):
I would say it's fundamental, speed of execution. I think in speed of decision-making. It's the thing that is probably the hardest to explain to people before they're here. It's hard to understand until you experience it. It's 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 Slack call in the person that we need in order to make that decision. And we'll be done with the decision today.

(00:27:44):
And like sure there are irreversible decisions you can't make that way, but for the most part, we really value the tempo of decision-making and the speed of response. And no company I've been at any scale, 5 people, 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 teams independently operating teams and all the rest of that is a really differentiating thing about the culture of the company.

Lenny (00:28:14):
I'm reading Kevin Kelly's new book where I don't know if you've seen his new book. It's all these little tidbits of advice and one of his pieces of advice is that usually the best time to do something is right now. And that feels like that resonates with the way you all think. I'm curious just how you create that culture and ability to make decisions fast. Is it purely top-down founder, this is how they behave, or is there something else that you found as effective to create this culture of moving fast, making decisions really quickly?

Jeremy Henrickson (00:28:43):
Obviously, a huge piece of this is Parker himself. It's an attribute of his personality, he likes making decisions quickly, and it's also a deliberate strategic decision on his part to have a company that makes decisions quickly. And so he models this constantly, right, in Slack, in conversations in person, and in every way possible. And there's an expectation throughout the company. If you kind of look at our leadership principles, 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 bake it in the way that we even do say quarterly planning. And the fact that there's this timeline for decision-making that doesn't leave a lot of room in the way that we expect people to know their domains, especially in product, right?

(00:29:29):
In product, you don't own little feature, you own your product and you're expected to be the world's foremost expert in it. And if you are, what that means is 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 give me 30 minutes, look something up and I can tell you what we need to do about that." And so all of those things in combination just yield an environment in which these decisions happen very quickly.

Lenny (00:29:55):
You talked about quarterly planning and you're saying that there's like, here's the timelines we need to make decisions on these dates, and there's a culture of just we stay firm to that. And if you don't, then we're going to move on.

Jeremy Henrickson (00:30:06):
That's right. And 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 get to retroactively make everybody react to the fact that you didn't operate quickly enough, right? And it's not a hostile thing, it's just a, people just have to get used to. It's a deep cultural principle. And the fact that everyone stands behind it just means it's gets reinforced on its own, out of its own gravity.

Lenny (00:30:34):
Do you have internal values that you've kind of outlined that are a part of this? Or is that not something that you find super valuable?

Jeremy Henrickson (00:30:42):
No, actually I find them quite valuable. And actually our COO, Matt MacInnis, 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 search 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, 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.

Lenny (00:31:23):
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 a 100 other companies who are actively hiring through this collective. And if you're looking around for a newer 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 any time and you'll only hear from companies that you want to hear 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?

Jeremy Henrickson (00:32:27):
I think it's really context-dependent, but I think it starts with whoever is in the role of making the top-level product decisions of them being one extremely clear 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.

(00:32:55):
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 walk all the way to ground and talk with the engineer who's writing the code on the thing. Because inevitably this top-level communication is insufficient to get to the detail of what matters and doesn't matter. And you don't have to do that everywhere, but if you do it in enough places, what it does is it creates a clear expectation of that kind of clarity across the board and forces everyone to 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 perform at their best. Right? And so we try to do that pretty frequently.

Lenny (00:33:43):
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 the end of what's possible. Recent story was IO talking about building the cash card and going to the warehouse and watching the printings of the cards and things like that.

Jeremy Henrickson (00:34:03):
Yeah.

Lenny (00:34:04):
I guess first of all, do you have a sense of where that came from and why that ended up being so important to y'all? And then two is there an example of you doing that or someone you've seen do that and that leading to something really important?

Jeremy Henrickson (00:34:16):
In the early days of our global efforts, when we were first trying to figure out what global payroll was, it was really tempting to say, "Oh, well we're going to go into the UK and that's going to be relatively similar to what we're doing in the US." But our 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 for how we think about learning about each of these countries and going into them and having a fulsome experience.

(00:34:50):
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 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 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. 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.

Lenny (00:35:30):
And so the leader of that team basically just went and studied the tax laws of each-

Jeremy Henrickson (00:35:35):
Yeah.

Lenny (00:35:36):
... country.

Jeremy Henrickson (00:35:36):
That's right, went all the way to ground. It's like, okay, let's go and open up the big old, I mean, it's online these days, the big old textbook and look like it's, or you're in the United States, it's 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, wow, how do I think about configuring these change unannounced? Some city administrator or the city legislature, whatever they call them, 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?

(00:36:14):
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 a regulatory or a 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.

Lenny (00:36:42):
And I think an important element of this that's between the lines maybe is don't delegate this to someone. You may have a tax expert on the team, and I imagine many leaders would be like, 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 at it.

Jeremy Henrickson (00:36:55):
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. That's an incredibly important part of our success is having that specialist but not before somebody with a product mindset. The tax specialist is amazing at tax, right? That's what they're, they love and that's what they do, but that doesn't make them necessarily a great product thinker. So the person with the product thing has to get into those same weeds first to really understand it.

Lenny (00:37:24):
Do you give any guidance and just how much time to spend on all that stuff versus the regular day-to-day of, say, a product leader on a team, it takes a lot of time to become a world expert on the tax systems of many countries, or is it just there's nothing more important than that, that is your job, and what are you doing not doing that? How do you think about it?

Jeremy Henrickson (00:37:42):
I think it's equally if a job is 80 hours a week, it's 40 of your hours. I think that you can't really understand a product unless you've gone there. Right? And yes, it takes time and you're right, you can't just ignore the other half of the job of communicating with the engineering team and writing documents or whatever, but what's the point of writing a document if you don't know what you're talking about? And so we very deeply value that. And it's one of the reasons that we keep, at least at Rippling, our product organization really thin. We expect a single leader 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 place to be.

Lenny (00:38:42):
I'm looking at this list and I just want to keep asking questions about it. One of the sure principles that I love is it reminds me of Amazon has the same principle I believe, which is leaders are right a lot.

Jeremy Henrickson (00:38:52):
Yeah.

Lenny (00:38:53):
Why do you find that to be important? I know you weren't necessarily design all these principles, but I imagine that something that you guys follow often and comes up a lot.

Jeremy Henrickson (00:39:01):
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 and they spend energy. And if they make good ones, the company does really well. And if they make bad ones, the company doesn't. And one of the things I really value in product leaders are people who can go into an ambiguous information with ambiguous situation, with incomplete information and a complex decision space and can look at that and listen to everybody and read whatever they need to read and say, this is where we need to go.

(00:39:43):
And even if everyone else is like, ah, 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. You can get it by talking with people and asking, "Hey, was this person usually right in respect?" And people think about it, but in the context of 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. 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.

Lenny (00:40:28):
Awesome. Shifting a little bit, I know you all are going through this global expansion. We talked about this a little bit.

Jeremy Henrickson (00:40:28):
Yeah.

Lenny (00:40:35):
And so just a few questions along this lines, because a lot of companies start 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 algorithm for that?

Jeremy Henrickson (00:40:55):
So it starts with an 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. Just makes sense to do that every country in the world. But you definitely want to be able to pay people in any country in the world 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, or when we made that decision, to have quite a few customers already, like thousands of customers. And so we knew not only where their kind of 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 US-based companies, which is incomplete data.

(00:41:35):
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 and how valuable is it to build in these countries? 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 where is there risk or where is this hard? Where is 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. The early decisions that we made on exactly which countries. We have subsequently reordered those over time. And as we've dove, dived in the 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.

Lenny (00:42:29):
Okay. And then the other question a lot of founders always struggle with is when is the time to start expanding internationally? Because there's pros and cons. Do you have a sense of what convinced y'all to start going international?

Jeremy Henrickson (00:42:41):
I think our case is slightly special, but I think the right answer to that question is always before you think you do before you think you need to because there are, 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, just as we care if there's not a U in color. There's just all of these subtle lessons that, like cultural lessons for companies that take a really, really long time to absorb. And so my view is you always should do it earlier than you think you should that, than you think you have to. In our case, it was always something we knew we had to do. In fact, we have a very clear thesis that companies that aren't global, particularly in payroll, but also in kind of insurance and benefits in IT. If you're not global, you're just not going to be around in 10 years because companies were becoming global, and then COVID happened and companies became global much faster.

(00:43:35):
It stopped being the province of 100-person companies plus and started filtering down into very, very small companies. It just became commonplace for small companies to be multi-country. And so that very much accelerated 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 that also kind of adds a little bit of a fire under the thing.

Lenny (00:44:06):
What have you found to be most surprising about expanding internationally to be successful in expansion? For folks that are maybe starting down this road of like, oh shoot, we should think about that.

Jeremy Henrickson (00:44:16):
I think the thing that was most surprising to me the first time I did this back at Guidewire in the [inaudible 00:44:23] 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 they're being a you in color or not. Or if you ever see a demo delivered to somebody in another country where they see a detailed screen about a person and it includes a social security number, it's like that you immediately lose credibility. Doesn't matter how good all the rest of your stuff is.

(00:45:08):
And I think 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. If you took a German system or something and demoed it in the United States with poorly translated stuff, we would think it would suck too. But it's not, it's really hard to adapt to that mindset. And so it takes just a lot of energy to overcome that organizationally.

Lenny (00:45:32):
Makes tons of sense. I'm going to go in a different direction now.

Jeremy Henrickson (00:45:36):
Sure.

Lenny (00:45:36):
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 how you crystallize processes and concepts for your team if you're not just like, Hey, here's our framework you should use.

Jeremy Henrickson (00:45:54):
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 so that the right decisions can happen and know more. And I think there's a danger, especially as companies scale, that you end up saying, well, if only we categorize everything correctly and Jira, like we will be able to make really good prioritization decisions. So I'm like, sure, extremely helpful to have clear categorization and things that Jira doesn't have like data and analysis and to be able to do all of that stuff. But what you really need to do is decide important to build and then have a way to build it really efficiently. And 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 their specific life cycle.

(00:46:47):
So you won't see me saying like, oh, we need to use this scrum thing or that combine thing, or whatever the latest, newest thing is. It's like, don't care about any of that. What I care is about something that's going to enable this team in this context at this point in their life cycle 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, everything does need in fact to be in Jira because otherwise, you can't rationalize about what's actually getting done in not.

Lenny (00:47:18):
Is there a process or framework that you find is counterproductive that you're just 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.

Jeremy Henrickson (00:47:31):
No, I don't find one to be particular, I don't consistently found one to be particularly problematic. So I think any framework sort of has its place, the right place, right time. I think there's danger any one time somebody like dogmatically says, I think we should use process X because that's 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 they 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's 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.

Lenny (00:48:08):
If you had to compare the way Coinbase builds product process-wise or just product development to Rippling, what would you say are the bigger differences?

Jeremy Henrickson (00:48:17):
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, what do we even need to build? What's going to survive? And so the process we had at Coinbase run, having those debates and getting to a decision and disagreeing, committing. And then from an execution point of view, being able to move fast. That was the trick 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 the mental model is actually of how I approach those things with the same, but they just yield different results in the actual making of the software.

Lenny (00:49:12):
What is that actual difference? Do you find day-to-day? Is it timeline differences? Is it how quickly, I don't know the way you structure, how far out you plan, what do you find is the concrete difference as a result?

Jeremy Henrickson (00:49:25):
I think the difference is in the day-to-day velocity of decision-making, because we can, Rippling, if you're on, I don't know, pick a random team. If you're on the device management team, 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. There's none of that cognitive dissonance. There is, we need to build this. It's hard to figure out how we need to build this, right? Because there's all these different things that we could leverage, but we need to basically get this done.

(00:49:58):
And so the kind of total velocity I would say is higher here, which does not say people work harder or less are at Columbia. Columbia was an amazingly fast environment, but it was also subject to the fact that you just don't know what the crypto markets are going to do, and you have to be incredibly reactive to that. And so I think maybe that's the one thing, like the reactivity to the environment and the crypto environment, what's going on, and the uncertainty of the regulatory environment, all that stuff. We got really, really, really good at handling those things really rapidly, which is something that we need to handle somewhat less [inaudible 00:50:34].

Lenny (00:50:33):
Sounds quite stressful at Coinbase.

Jeremy Henrickson (00:50:38):
Yeah, I mean it was fun. Yes, it was stressful. I mean, every job I've ever had has been stressful, but in its own unique way. But all of that stress I think 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. But yeah, it's stressful.

Lenny (00:51:00):
And looking back, what a joy.

Jeremy Henrickson (00:51:02):
Yeah. No, there are very good memories. I look back, I don't really, I 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.

Lenny (00:51:21):
That's what I find too. You go through these hardships and then you look back and you're like, wow, that was so cool. But assuming they go well, assuming the company works out and-

Jeremy Henrickson (00:51:21):
True.

Lenny (00:51:29):
... it feels like it was successful. A lot of times you're at a startup, your life sucks for two years and it doesn't work out and that there is a lot of upside and good memories to that, but it's less glorious.

Jeremy Henrickson (00:51:41):
Yeah, that's fair though. I mean, the first company I was really at out of school's company called Reactivity back in internet one era, and we were trying to figure out how does this internet thing work and how do we start companies on the basis of these tech new technologies and how do we help other companies build stuff and figure it out? And that company fundamentally didn't work out, ultimately got kind of spun itself out and got acquired, which was great, but it was this extraordinary set of people that I was so lucky to work with and I loved all the time I spent there and it was foundational to everything else I ever did. And so even though that effort didn't pay off in the traditional set, the value of the learnings I had there and then the people I had a chance to work with was just really exceptional. So I feel very lucky.

Lenny (00:52:30):
That's a really good point actually. And I think I should correct even what I said that even when things don't work out, traditionally those experiences end up being incredibly valuable in all these unexpected ways.

Jeremy Henrickson (00:52:42):
Yeah, 100%.

Lenny (00:52:44):
Yeah. Okay, so final topic.

Jeremy Henrickson (00:52:45):
Sure.

Lenny (00:52:45):
I want to talk about hiring product managers and interviewing.

Jeremy Henrickson (00:52:48):
Yeah.

Lenny (00:52:49):
So you've hired a lot of PMs over the years. I'm curious, what's something you've learned about what to look for in product managers and also just in product leaders that other people may not be focused on as enough?

Jeremy Henrickson (00:53:00):
I mean, I don't know that I have any particularly special insight here. I think there's a couple things that I do ask that maybe are more of an emphasis because it's Rippling than not. But the first of those is when people are 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 actually too complex for people to have all of the answers upfront. There's just the space of the problem is too large to do that, which means that in the interview there's a lot of opportunities or in the case study there's a lot of opportunities. So just ask ad hoc questions 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.

(00:53:47):
And some people are extremely good at that here in assumption and they blink a couple times. They're like, oh, well that has these 400 implications. And they just start rattling them off. And some people get really flummoxed. I mean obviously for our environment, that former is 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 actual interest in the job.

(00:54:14):
People tend to ask better questions when they're more excited about working at a place and done their research and are asking people about it. And also the quality of those questions can vary quite dramatically. And that's okay. I don't expect the quality to be the same all the time, but sometimes people ask a question, I'm like, "Oh man, I would've 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.

Lenny (00:54:42):
Is there an example of someone asking a really good question that comes to mind that you think back to and like, Oh wow, that was great.

Jeremy Henrickson (00:54:49):
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 these products and you have this employee system of record thing underneath it, we be thinking about how to create these various pillars of underlying platform technology, things like [inaudible 00:55:22] all this stuff. And this was before we fully formalized the concept of our platform beyond the kind of employee system of record.

(00:55:29):
And I remember thinking, yes, we should, and that had entered our minds before, but the fact that somebody which who had almost no context on the company, that's what was impressive about this question. It's like, man, you've been thinking about Rippling for a couple weeks while you're interviewing with a bunch of other companies or whatever. And 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 think through the sorts of things we need him to think through.

Lenny (00:55:58):
And I think it touches on PMs need to be business leaders and great questions are often about the business and the future of the business and how to make it run more efficiently and this, and there's a product org element to it. But I find that that's a really underappreciated element of PM interviews, just thinking about the bigger business, not just the PM product.

Jeremy Henrickson (00:56:19):
For me it's two things. It's thinking about the bigger business and having the context around whether it's 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 with Jeremy that you said earlier is all of these things. And their ability to understand that this isn't a simple business, it's really hard, it's really complex. And the ability to have these insights to help them think through those details is really cool.

Lenny (00:56:49):
You talked about this prompt you give product managers not to give away what you actually asked these days, but is there an example of a prompt that you've given in the past or you think is a good example of a type of prompt to give a product manager candidate.

Jeremy Henrickson (00:57:01):
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. So when we do, so our process overall is actually quite short. It's basically get in contact with us somehow, eventually get 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. Modulo, other conversations around the edges. And the questions that matter are around how do people think through that product discussion, 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?

(00:57:53):
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 the depth that they're thinking or their interest in engagement in the role. And at that second discussion, it doesn't have to be perfect or anything, but it is a very strong signal when people, whether they've thought through a set of questions they want to ask or just on the fly 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.

Lenny (00:58:30):
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?

Jeremy Henrickson (00:58:41):
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've already built it. And so having, no matter how smart you are, there's a lot of smart people out there. 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 that you can actually have the humility to say, 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.

(00:59:12):
And so I found that that humility is one of the biggest differentiators in early career leaders who are able to let go of how awesome they were in school or in their first job or whatever. I mean, I had to do this and realize the job is always hard and the job is always about discovery every single day. And if you can maintain that curiosity and elasticity of thought and creativity and light coming solutions could be awesome. But if you close yourself off to that and think you always have the right answer, then there's like no hope.

Lenny (00:59:49):
This touches on another principle that I still have sitting on my screen here, which is great leaders change their minds a lot or just change their minds.

Jeremy Henrickson (00:59:57):
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 being in 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.

Lenny (01:00:19):
The 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 product 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 the product should be?

Jeremy Henrickson (01:00:47):
Yeah, no, that's a great question. So I think you've got to be adaptable, right? It's like any other relationship, right? You have to understand what the nature of that relationship is, where that person's going to care, where you're going to care, the ways in which you can challenge each other. I think fundamentally you need to make sure that person is willing to be challenged, right? So I've seen product leaders or CEOs who are kind of unwilling to be challenged and I wouldn't be able to work with those people.

(01:01:17):
But yeah, Parker is incredibly strongly opinionated, but he's also incredibly informed, which makes for some really, really great debates. And I've just found that whatever, and it's not even 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 a moldable puzzle piece where I can just fit in. I think that's actually one of my core skills. And so that's worked out for me and Parker and I before I started 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 can have a totally reasonable discussion about it, and that's what makes it fun.

Lenny (01:02:06):
Adaptability actually is, I took a strength finder test once of finding my own strengths and that was my number one strength is I'm [inaudible 01:02:14] I think we share that.

Jeremy Henrickson (01:02:15):
That's excellent.

Lenny (01:02:15):
Yeah, seems like an important attribute for being in a place in. Well with that, we've reached our very exciting lightning round. I've got six questions for you if you're ready.

Jeremy Henrickson (01:02:25):
All right, I'm ready. Hit me.

Lenny (01:02:27):
Here we go. What are two or three books that you've recommended most to other people?

Jeremy Henrickson (01:02:31):
Well, first is my favorite series of books ever, which is the Baroque Cycle by Neal Stephenson. It's a nine-volume epic or three-volume, nine-book epic depending on 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 Iain Banks, which is just super fun, far-future sort of universe that I've really enjoyed.

Lenny (01:02:59):
What's a favorite recent movie or TV show?

Jeremy Henrickson (01:03:01):
Watched The Last of Us, was an avid fan of the game and I thought they did a really nice adaptation. Favorite mov, like I guess, recent movie, it's not that recent, but I really like Tenet, which I thought was a, I was impressed with their ability to go there and make that movie and I just really enjoyed it end to end.

Lenny (01:03:23):
It kind of ended, but we had a drinking game anytime someone mentioned Last of Us, which took over White Lotus. I'm going to drink some tea right here.

Jeremy Henrickson (01:03:30):
Okay, fair enough. I'll try. I've only got water normally I got tea, but water today.

Lenny (01:03:33):
That works. But it's interesting, it hasn't come up often, so I think maybe we end that for now and see what the new pattern emerges. And then Tenant feels like, I was just thinking it feels like a compound movie, compound startup as a movie, a movie is very complicated too to stay-

Jeremy Henrickson (01:03:50):
Yeah, That's why I enjoyed it. I like trying to figure out the multi-timeline chart in my head as the movie progressed.

Lenny (01:03:56):
The puzzle piece within you trying to find all the puzzle pieces.

Jeremy Henrickson (01:03:59):
Yeah, for sure.

Lenny (01:04:00):
What is a favorite interview question you like to ask? You already maybe answered this, but anything else come to mind?

Jeremy Henrickson (01:04:06):
I think I did, no, my favorite one is What questions do you have for me by far?

Lenny (01:04:09):
Great. What are some favorite products you've recently discovered that you love?

Jeremy Henrickson (01:04:14):
I guess I'll just mention, I don't know if I go 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 super easy to use and really adaptable to lots of motherboards. 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 late last week, and had to do some really quick research into my new favorite pair of headphones. And these Focal Bathys are super nice. I'm a bit of an audio file. I like to listen to classical music and ambient stuff, so we need a lot of dynamic range and noise cancellation and these have been great so far.

Lenny (01:04:57):
Okay, so what are they called?

Jeremy Henrickson (01:04:59):
Focal, I think it's Bathys, B-A-T-H-Y-S. Okay.

Lenny (01:05:04):
And has there a specific model or there's like that one?

Jeremy Henrickson (01:05:06):
That's it.

Lenny (01:05:06):
Okay.

Jeremy Henrickson (01:05:07):
You'll know it when you see it.

Lenny (01:05:09):
Okay. We will link to them in show notes, so 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?

Jeremy Henrickson (01:05:20):
Maybe the most recent innovation sort of at Rippling was the kind of introduction of what I'm calling imperatives. These things that whether they come bottom up or top down are things that like everybody across the entire product and engineering team needs to do and what's important about that list of things that are not on it. And in a world where we could choose to do hundreds of things at once, being able to force rank that list of things, draw a line, say these are the ones everyone has to do, has created a lot more focus and clarity than we had before.

Lenny (01:05:48):
So imperatives are essentially here's the priorities for the next, say quarter six months here?

Jeremy Henrickson (01:05:53):
Here are the priorities for everybody and now integrate that into your own team's priorities, right? So each team still is building their own priorities, but they have to factor in this set.

Lenny (01:06:05):
How many of those do you usually have? This is awesome. I like this tip.

Jeremy Henrickson (01:06:09):
It depends on what level of granularity you want to talk about them at, like maybe 10, right? 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 pretty natural part of a company's evolution and we're just in that part of the cycle, so-

Lenny (01:06:33):
Awesome.

Jeremy Henrickson (01:06:33):
... used it.

Lenny (01:06:34):
Final question, what's a question I should have asked you that I didn't ask you?

Jeremy Henrickson (01:06:38):
I guess, what do I do with my kids maybe? I have two kids, they're nine and-

Lenny (01:06:38):
What do you do with your kids?

Jeremy Henrickson (01:06:43):
... 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 as we get to start playing Gloomhaven. So that's going to be fun.

Lenny (01:07:12):
I don't know either game, sounds very hard and complicated.

Jeremy Henrickson (01:07:15):
They're fun. They're fun.

Lenny (01:07:17):
Amazing. Jeremy, we covered a lot of topics. I feel like this is a compound podcast episode and so thank you for spending time with me. Thanks for being here. Two final questions, working folks, finding online if they want to reach out, learn more, and how can listeners be useful to you?

Jeremy Henrickson (01:07:32):
Awesome. LinkedIn is the easiest way online and 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.

Lenny (01:07:46):
What's the best way to explore those roles and apply? The

Jeremy Henrickson (01:07:49):
The website has by far the best channel. It gets to this right recruiter who will tell me about it right away.

Lenny (01:07:55):
Great, surfline.com and there's probably a site for careers.

Jeremy Henrickson (01:07:58):
There is a career site on there that you, pretty easy to find.

Lenny (01:08:00):
Okay. Rolling to that in the show notes. Jeremy, thank you again for being here.

Jeremy Henrickson (01:08:04):
Thanks so much for having me. This was a lot of fun.

Lenny (01:08:06):
Hi everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or a leaving 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.