very very tempting to to kind of float up here as a leader and say Hey you know you take that hill over there you guys do this over here when in fact like where you really learn where the challenges are or the problems or the successes is by like just like being there with with the people in the
trenches on like one of the things like whichever one seems hardest or most complicated so I try to do that as often as I can and I found that I always learn a lot by by going through that detailed exercise welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their
hard-winning experiences building and growing today's most successful products today my guess is Jeremy Henriksen Jeremy is senior vice president of product at Rippling where he leads the product and design teams previously he was Chief product officer at coinbase where he oversaw 10x growth of the
product in engineering organizations and helped scale coinbase during one of the craziest times in the crypto markets in your conversation Jeremy shares his lessons of 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 design for the most complex use cases first and tons more enjoy this episode with Jeremy Henriksen
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teams of every size and see what mixpanel can do for you at mixpanel.com friends slash Lenny and while you're at it they're also hiring so check it out at mixpanel.com friends slash Lenny thank you Jeremy welcome to the podcast thank you so much for having me I'm excited to be here so I've heard nothing but amazing
things about you and I'm excited to learn from what you've learned from your experience at Rippling at coinbase and all of the products and teams that you've built and so thank you again for being here yeah super happy to be here so I want to start with a with your time at coinbase where you're a chief product
officer and your Chief project officer during maybe the craziest time in the crypto markets it was a I think 2016-2018 when I was looking at the Bitcoin prices and it was like it went from like a thousand dollars to twenty thousand dollars I think in a matter of months so yeah I'm curious what was that
experience like and in particular what was like leading a product team through that experience the strongest memories for me for me are during like 2017 where crypto which had kind of been at its nadier in like early 2016 it kind of slowly started climbing out I'm just
kind of took off and became a real thing in the in the public Consciousness and and you know coinbase which at the time had you know an exchange just like on-ramp and off-ramp from Fiat to crypto and back experienced over the course of 2017 40x growth in in usage that's like a dream come true for for a lot of
people it's it no I mean it it was it was both a dream and a nightmare um you know and I was I was incredibly lucky to be working on it with a with a team of people that I could really trust and constantial to shoulder with in the trenches and it was a lot of learning about how you can rapidly scale systems
you know over time and you know people like to trade crypto on Saturday mornings and so a lot of Saturday mornings there's like some new like like thing would break on the edges of the system and we need to kind of get in there and and and work on it and so it was just a lot of really incredible
lessons about who you choose to work with and focus and making sure you have the right people in the room at the right time okay so let's unpack a couple of those so focus is really interesting and something people always talk about but you know hard to actually do I guess how did you keep the team focused I
imagine just like you know everyone's getting rich all over the place in crypto things are breaking all the time like how did you maintain focus on on your team well the first thing is you don't talk about people getting rich it's like it's a it's a very technical it's a very technical you talk about
like it's customers it's their money right and number one it had to be secure right so there's a guy named Philip Martin in front of mine now and he's he's just this amazing like security leader um at coinbase and he was able to always put these like decisions that we were making extremely quickly like in context
right and say look these are the kinds of decisions we can make and still have it be secure no matter how fast we need to move and so security was always like the number the number one thing and then the second thing is like focusing on like the the both the kind of immediate
nature of the issue hey site is down or whatever I'm like resolving fat but also trying to set those in the context of like where we need to go over the next six months like what are we actually shooting for what do we believe the volumes are going to be what's it going to take to to have you know everything
from a user experience to kind of the the Deep back end of the product that would actually work for them what was maybe the biggest challenge as a product leader trying to keep people focused and everything on the rails as things were going 40x I think the biggest challenge was that in crypto
there's just so much uncertainty in general like simple questions like is ethereum gonna be a thing right are the subject of debate and no one actually at the time had an answer to that question lots of really strong opinions and so you have to be able to have those debates because because Lots is going
Lots is going on but then you have to be able to come out of those conversations with a clear kind of company point of view that you're all that you're all shooting toward and like while there may still be differing points of views and debates that happen on the margins like you go full speed toward this answer
until you decide to go full speed toward a different answer and I thought we were pretty successful at that um at coinbase and it wasn't always easy maybe just the last question there sure living through a time like that a lot of people are going through these periods of just like intense work and it's like
holy moly this isn't crazy stressful working like incredibly long hours but then you look back at those times and end up being the most important meaningful periods of your career I guess one is that is that your experience too and then two I guess is there any advice for someone that's
maybe going through something like that of just like here's uh here's maybe the silver lining of being in a period like that so it's hard right it wasn't wasn't always easy I had like a new daughter who had been born just a few months earlier right really tough to like kind of balance balance those things but I've
always loved the rate of learning and and so like those it is those experiences I feel that like have most sort of accelerated my own personal growth and personal learnings because it's in the in The Crucible of things being hard and so I think when people are going through those times it's nice
to take like you know a step back and talk with friends or whatever about like what's really what's really going on and setting it in the context of hey you know three four five years now from now when we look back on this we realize wow you know we a we did something amazing with that time and B we we learned a lot
and we were able to take that with us kind of into the into you know whatever we were doing next after that before I Chad asks you what people ask you for advice most around and you said that it's that people often ask you for advice on how to maintain velocity at scale which uh something every founder
and product leader is always striving to do and so what have you learned and what do you tell people about maintaining and maybe even improving velocity as you scale I think there's a lot of different answers here and I think a lot of them are are very specific to the nature of the business that someone's in right
different businesses can maintain velocity in in different ways I think there's kind of a universal truth that you want like small teams with clear missions right you know if if there's 300 people trying to work on one thing like just sheer like communication challenges done by this number all of
those things come into play and it's really really hard to act quickly and so having smaller groups groups of people breaking down what is always a very very large problem into like sufficiently small small bits that small groups can attack wholeheartedly and minimize like
horizontal communication I think is is the first thing I think the second thing is that to the extent it's like a technology problem the more you can bake into like a a clear platform um it reduces like the decision-making complexity for everyone who's working on like the domain part of the problem and
so like a clear platform with a clear interface easy to use and all the ways that both engineers and product people want it to be easy to use simplifies the the space in which people have to think about these problems um and that's not always easy right platforms are not you know you can't just like write a
platform and hope it's going to work for the products it's very much an iterative thing but the more one can invest in that and have the right kinds of people who are capable of doing that sort of both systems thinking and product thinking simultaneously um I think is really important the third
thing just from a leadership point of view is like diving deep right like it's it's very very tempting to to kind of float up here as a leader and say Hey you know you take that hill over there you guys do this over here when in fact like where you really learn where the challenges are or the problems or the
successes is by like just like being there with with the people in the trenches on like one of the things like whichever one seems hardest or most complicated and so I try to do that as often as I can and I found that I always learn a lot by by going through that detailed exercise and I think the last
thing is it's just making sure that teams have like the right distribution of like experience and and seniority like sometimes you get a team started did and the team is like perhaps doing something that's like zero to one and they're amazing at all this zero to one stuff and then like two or three years
later like those same people are trying to like scale the product to like you know millions of people and it turns out that a they don't like that part of the job as much and B maybe they're not as good at it so I think you understood you constantly like look at the team and make sure that a people are doing things
that they love and if they're not like hey let's try this other thing instead right and and be like recalibrate the team and make sure like the right kind of skill sets are there and I found if you kind of do all of those things and then have product leadership where we're
saying this is what we need to do right in a very very clear and precise on 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 okay let me dig into a couple of
these These are really good please um so with the small teams with clear missions is there an example of that at Rippling or coinbase where that was like a really good example of this being true one example is maybe three years ago when I when I was uh just starting at the company um we decided that we needed to build a
time in attendance product um 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 I have Parker CEO also spend time on it and you start there right and Sasha's brought a few people on with him and those four people over the course of maybe nine months or so built a time in attendance product it was the only thing they were doing they
didn't have to worry about what was going on with our payroll product accepted the extent they had to integrate with them a little bit right they didn't have to worry about what was going on with the kind of the benefits team or kind of our it products they were they were mono maniacally focused
on this one thing and then identifying to places where yes there's connectivity to the rest of the suite and that allowed them to move extremely quickly how much of that was Parker being on the team helping them unblock everything versus being very small and focused I think it was mostly small Focus like
obviously Parker can like do things and unblock them in the way that only a CEO um Can in that and that helps the thing is that Rippling like we've now replicated that like you know a dozen times right that's our model first for starting new things and so it can't just be him unblocking things so he does
unblock things it's more that like this pattern of having these small groups like be able to do things and then being able to like go to those people right whether you're Parker or somebody else in the company and be able to say hey how are things going or you know we working on the right things or let's see
the latest designs for that thing and comment on it like all of those things can happen just at a much greater Tempo than if you're like trying to go three layers down into the org and and do things I think that's the other maybe the key Point here that like everyone is
exposed to senior leadership like yes we have like a management structure because you have to but that management structure does not interfere with the ability of kind of anyone anywhere in the organization to kind of like look at what's actually happening and that happens very directly so let's talk
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 here
what is what is that model roughly yeah so the model is quite simple in in the vast majority of cases we realize we need to build something and we have you know the one page view of what that is and usually we're lucky enough that the things we're building sort of exist in some form in the industry today not in
the differentiated way that we can build it but like time and attendance is an example like that's a well-known thing in the industry there's whole companies that do only that right so we start there we find a single engineer who is extremely entrepreneurial understands what it means to operate at Tempo
understands what it means to like make decisions with low information understands how to work very very quickly with like a design partner so we have a design partner and we say look come into 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 like 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 um and during this intervening time they're also recruiting right a team of usually two three four other Engineers who kind of have that same zero to one mentality and they start building and uh usually over the course of like six to nine months we can get a product from you know a blank
sheet of paper to something that is launched or at least that we're using sort of internally when we dog food our our stuff really heavily um and then it grows from there and then sometimes when you launch one of these products get close to launch you realize hey actually a team of five or six
people can like kind of handle this product at 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 on the product but that that's the general
life cycle and then you you keep growing and scaling it that is fascinating so just to understand you find a Founder type to kind of take the lead on a new idea and do you recruit them internally or you sometimes find them externally just to focus on this stuff interesting okay and then you find a
design partner for them to work with to figure out what exactly needs to be built and is it idea pick one design partner or you try to encourage a few um usually it's one like so there's a designer right so we have you know a design oh a design partner meaning a designer not a company that is like
their partner and design oh no no no no like literally somebody who who who knows rippling's products knows like our component Library knows all that stuff and is is skilled and like doing you know ux and you know interaction and visual design got it okay designer okay good 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 that maybe grows the team maybe not yep that's right and like you know every you know it's a pretty ad hoc but every couple of weeks or something like that
they're meeting with like me or with Parker or you know whichever one of us is like the dri on it and like giving feedback on the designs kind of having a critical life or like oh man if I were using this as a admin you know a small company or an admin at a large company how would I feel about this would this
interface work for me and so we we're pressure testing it like kind of throughout throughout that cycle and trying to get the balance of like you know speed and comprehensiveness right this reminds me you're also I hear not a big fan of MVPs that you like Building Products to further to further point is
that is that true and then if so how do you how do you think about the initial version of a product first of all I don't want to knock on MVPs I think MVPs like have their place they're extremely useful particularly if you're you know literally at a zero to one company that's never done anything before and
you don't have like clear Market validation I think in our case specifically for for Rippling a minimum viable product would do a disservice like to both our customers and to like the very team that was building it and the reason I believe that is that when when you design a minimum viable product
you're optimizing for Speed and in that opposite of optimizations you are minimizing the deeper product thinking about what can like fully differentiate our product based on not only existing kind of capabilities within our products and platform but based on what it ought to do in the future and so sort of
limits product creativity but worse it leads to building the wrong thing technically right so if you're only thinking through the simple cases and you're an engineer and no one's pushing you on saying wait what about that you know Healthcare or Hospital Administration case where like you know
it's Mission critical in life then you're going to make a different set of architectural assumptions and then you're going to build on those and you're going to build on those for six months nine months a year and you'll have dozens or hundreds of assumptions built on top of those and it's extremely
difficult to unwind those decisions once you've built them into the product and and therefore you know we believe very deeply it's like sure understand those simple cases right understand if you're a two-person company you don't need all of these other things and what is a product look like for you to approach it
but also understand what it would mean to have 10 000 people globally around the world with this like ridiculously hard use case what's the model that would support that right and let's make sure that as we're doing the technical and product design for this thing that it accommodates that
view even if we're not going to support it in the first version right even if we make like the product decision to say like look we actually don't need to handle that case right now you still build the product in a way that's not going to that's not going to prevent you from getting there in the
future and does that take a little more time sure yeah but does it save you time in the long run absolutely right and so um so that's our approach is there an example that comes to mind of a product you build at Rippling or coinbase of just like it could have been this really simple MVP and then ended up
being like no we did the right thing by building it further along the Spectrum yeah so I think a great example of this at Rippling uh is our Global payroll product right we could have said hey look um we just need to support this one country right we need to support uh whatever the UK let's say so we're going
to copy all of our us stuff like just replicate it and like change all the things to be UK like that would have been the fastest thing to do to dramatically it'll oversimplify right but that's not what we did what we did is we said look we need to launch with six countries and these are six Super
different countries that we that we want to like look at and they're going to have different requirements from like an hris standpoint from an employer of Records standpoint from how you pay Global contractors from how payroll works and we're going to make a system that works for those countries there's
like lots of Downstream implications for that but what it means is that now our Global payroll system adding a country is something easy but it's a lot easier than it would have been if you had to like continue to stamp out and replicate and then of course maintain all of these things that have very little underlying
connectivity and instead what we have is like you know eighty percent of the system is baked into our Global payroll platform and then like the 20 percent is like country specific and most of that specificity can be handled out by Engineers right who are very very expensive to change things that are like
local specific but instead can be configured by somebody that's in compliance by somebody that's in legal that needs to get the right documents into the system and all of that stuff can be handled by by the system which allows us to move much faster sort of going forward I've heard you describe this kind of
idea as you encourage teams to design for the most complex use case first is that kind of the instruction you give these teams 100 many times and so it's one of these things that like until you're here it's a really difficult thing to kind of grock because a it's so Counter Culture to what like the
background that most people have come from it's like no no don't think about all those things just like zoom in on this on this one case use it as a wedge and then go from there this is one of the reasons that we have people especially new people in these kind of founding roles come in and spend a few
months just like absorbing the culture or to like really really learn really learn these lessons and it's one reason that we're extremely high touch with kind of new products in their infancy to make sure that we just don't fall into that trap right especially because like
simultaneously with doing this we're like hey but we need to ship this as fast as possible right and so you want to get the the balance of those two things right so when I think about Rippling I think of you get kind of the culture is to do things the hard way and the the right way and an element of that
is there's this concept that 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 MVPs and you know build new products the idea of a compound startup for us is
that we're basically a lot of businesses that all work together right like if you think about about the products we offer we have payroll well there's entire company is built just on payroll insurance and benefits entire companies that's their entire life in fact like a fragment of benefits is the entire life
cycle of the whole company you know our it products device management and identity management time and attendance each of these things are Industries into themselves with like multi-billion dollar companies serving each of them the Insight Parker had you know before he founded the company was like actually
the result you get that when you have that is that there's all this data that gets replicated and copied and is impossible to keep in sync everywhere the right answers to have a single system of record one place one database where all of that information is resident so that each of these
Downstream systems can always have the right data at the right time and then you can build on top of that you know things like workflow and Reporting and analytics and permissioning and all these kind of underlying capabilities so the idea of a compound startup is like all of these different businesses benefit
from being built on top of one platform the activation energy for that is extremely high right so before my time at the company you know Parker Persona the technical founder and others you know built all of the first versions of all of these products and it was a minor miracle when they were able to do that
but having done it right we then had that platform and we could continue to build like new verticals and new startups right on on top of that um on top of that Foundation this touches on something that comes up a number of times in this podcast which is the importance of differentiation and
it feels like this is the differentiator for Rippling it's not going to be just a better one of these vertical solutions that the main differentiators we're going to do it all and everything's gonna be so much better because it's all in one platform is that is that kind of where the original idea came from or is
there a different way to think about that yeah I think that's right so I mean the the fundamental contention is having a single system of record is better for many many reasons right the most simple of which is there's there's a single source of Truth and like all of these other products can rely on it but also
unless you start with that Assumption of everything being in a single system of record there's a bunch of other things you can't do right you can't you can't build out a I don't know a permissioning system that looks at the various attributes across all of these products you now suddenly have to do an
integration in each of these products talks different languages you can't do simple things like build a product and say who is this person's manager most products you can't do that most products you find some system of Truth export everybody's name and email address in a spreadsheet you know have another email address or
another name maybe an employee ID of like who that person reports to and upload that to another system which by the way is immediately out of date because organizational structures change all the time whereas it's Rippling it's always correct right we are the system of record so all of our products they're
like hey who's that person's manager in the system immediately knows right that's a very very simple example of something that that you can only do if you start with like solving to come back to an earlier Point like solve the most complex use case first right solve the fact that this data all needs to be in
the same place and so our ability to kind of differentiate right boils down to kind of that one fundamental decision which just allows us to do things that are literally impossible for any other company to do what would you say is uh one of the most unique things about rippling's culture
that maybe you haven't mentioned yet I would say it's fundamental speed of execution right I think in speed of decision making it's the thing that is probably the hardest to explain to people before they're here like it's hard to understand until you experience it like let's not schedule a meeting for next
week or tomorrow or later today you know we're in the middle of the meeting we need to make a decision Let's either make the decision or if we can't let's like slack call in the person that we need in order to make that decision and we'll be done with the decision today and like sure there are irreversible
decisions you can't make that way right but for the most part we really value like the tempo of decision making and the speed the speed of response and no company I've been at at any scale five people you know 5 000 people has ever operated at the tempo this one does and I think
that our ability to continue to operate at that Tempo which is partly due to the fact that we are a compound startup and have these small teams independently operating teams and all the rest of that is a really differentiating thing about the culture of the company I'm reading Kevin Kelly's new book or I don't know
if you've seen his new book it's all these like little tidbits of advice and one of his pieces of advice is that usually the best time to do something is right now and that feels like that resonates with the way you all think I'm curious just how you create that culture and ability to make decisions fast is a purely
top-down founder this is how they behave or is there something else that you found is effective to create this culture of moving fast making decisions really quickly obviously a huge piece of this is like Parker himself right it's an attribute of his personality likes making decisions quickly and it's also a
deliberate strategic decision on his part to like have a company that makes decisions quickly and so he models this constantly right in slack in conversations in person in in every way possible and there's an expectation kind of throughout the company if you kind of look at our leadership principles like
this ability to make decisions quickly is something that kind of everybody promulgates but also I think there's a number of things we've done to sort of like bake it in right like in the way that we you know even do like say quarterly planning and the fact that like there's this timeline
for decision making that doesn't leave like you know a lot of room in the way that we expect people to know their domains especially in product right and product you're you don't own like little feature you own like your product and you're expected to be the world's
foremost expert in it and if you are what that means is like instead of having to come back to people three days later with an answer just off the top of your head you can be like yes this is what I think I should do about that or you know give me 30 minutes to look something up 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 he 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 yeah we're gonna move on that's right and so and so and it's it's shocking to people when we actually move on right that haven't been here yet it's like no no that date passed you know what you don't get to like retroactively like like make everybody react to the
fact that you didn't operate quickly enough right and it's and it's not a it's not a hostile thing right it's just a people just have to get used to it so it's a it's a deep cultural principle and the fact that everyone stands behind it uh it just means it's like gets reinforced on sort of its own out of its
own gravity do you have values like internal values that you've kind of outlined that are a part of this or is that not something that you find super valuable no we actually I find them quite valuable and actually our rco Matt McGinnis who you know joined the company about a year
before I did you know he has been the one to like really drive this and you know you go to I can't remember the specific URL but on Rippling there's a search for Rippling leadership principles you know there they are um and they are really true to the culture of the company the way we came
up with them it was to us you know a couple years ago to introspect into what the what actually made people successful at the company like who's successful why are they successful why do they enjoy being here or alternatively the opposite right like why people not worked out why do some people like not enjoy it here
and like those are the things that are differentiating and those are the things that we wrote down 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
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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 what piece of advice would you give someone for helping them do this at their company I think it's really context dependent but but I think it starts with you know
whoever is in the role of like making the top level product decisions right of them being one extremely clear about what those priorities are and more importantly extremely clear about what all the priorities aren't right like there are so many things that like could be important or people can
make the case for being important or whatever that like are fundamentally distracting from like the core mission of getting something done but secondly for that person to go all the way to ground on it right we have a we have one of the leadership principles is go and see right so to to to look at the thing
and then like walk all the way to ground and like talk with the engineer who's like writing the code on the thing because inevitably this top level communication is insufficient to get to like the detail of like what matters and doesn't matter and you don't have to do that everywhere but if you do
it in enough places what it does is it creates a clear expectation of that kind of clarity sort of across the board and like forces everyone to sort of like up their game a little bit and just helps people understand what the expectation is right I think in the absence of those sort of clear expectations it's
difficult for people to like perform at their best right and so um we try to do that pretty frequently okay I definitely want to spend more time on this but uh before we get there uh so go and see I love that and that actually has come up recently on a number of podcasts just the importance
of people continuing to ask questions and going to like the end of what's possible a recent story was IO talking about building the cash card and going like the warehouse and watching the printings of the cards and things like that yeah I guess first of all you have a sense of where that came from and why
that ended up being so important to you all and then two is just is there an example of you doing that or someone you've seen do that in sh and that leading to something really important in the early days of our kind of global efforts right when we were first trying to figure out like what Global payroll
was it was really tempting to say like oh well we're going to go into the UK and that's going to be like relatively similar to what we're doing in the U.S but our kind of had a payroll went in and said like actually here are the ways in which like we knew it was going to be different but here
are the ways in which we didn't anticipate that it was going to be different which made us realize that we had to completely alter our approach right for how we think about learning about each of these countries and going into them and having like a fulsome experience and 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 like satisfy the needs of every country in which we're going to run payroll right and it was only through that like very early on like deep look
at how one country was actually operating and then doing the same thing with the next country that like we were able to set in motion all of those things right it's not like we knew all the answers at that point but it allowed us at a much earlier stage to put in motion a bunch of stuff that we need to
do the thing got subsequently much more clarified and much more precise over time and so the the leader of that team basically just went and studied the tax laws of each country that's right like when all the way like went all the way to ground it's like okay like let's go
and open up the big old like I mean it's like online these days with a little textbook and look like it's like or when you're in the United States like you have to go look at Ohio or Pennsylvania which have all these like little like local like City or county-based taxes um and it's and it's incredibly instructive
to look at just a few of those and think like wow how do I think about like configuring these change like unannounced right like some City administrator you know or the city legislature whatever they call them right they decide to change the tax rate well how are we going to know about that
how are we going to change it how are we going to change it so it's effective at the right time and you don't think about those things until you've gone all the way to ground and looked at how these things are actually actually worked how they're communicated and how they're thought through and I think the same
thing is true of every aspect of every product you know in different ways right it might be a technical thing it might be a design thing it might be a compliance or regulatory or governmental thing but whatever it is that detail always exists and unless you're getting down there and seeing and understanding
it firsthand you don't really understand what your product needs to do and I think an important element of this that's between the lines maybe is don't delegate this to Someone Like You may have a tax expert on the team and I imagine many leaders would be like go go figure this
out and tell me and I think what you're saying is you go do that and learn become the world X that's right that's right you go do it you go learn and then we can make the case for hiring the tax expert right which we do have by the way now right like that's that's an incredibly important part of our success
is having that specialist but not before somebody with a product mindset like the tax specialist is amazing at taxed right that's what they're that's what they're they love and that's what they do but that doesn't make them necessarily a great product thinker right so the person with the product thing has to has
to get into those same weeds first to really understand it do you give any guidance and just like how much time to spend on all that stuff versus like you know the regular day-to-day of say a product leader on a team you know there's it takes a lot of time to become a world expert on the tax uh systems of
many countries or is it just like there's nothing more important than that that is like your job and what are you doing not doing that how do you how do you think about I think it's an equally you know if a job is 80 hours a week it's like 40 of your hours like it's it's I I think I think that that it you
can't really understand a product unless you've gone there right and yes it takes time and you're right you can't just ignore like the the other half of the job of you know communicating with you know the engineering team and like writing documents or whatever but like what's the point of writing a document
if you don't know what you're talking about right and so and so we very deeply value that and it's one of the reasons that we keep at least at Rippling our product organization really thin right we expect like a single leader right to be able to know like the full scope of the product in fact great product
leaders can in fact do that because they like have this native curiosity and and interest and like ability to absorb a lot of stuff and uh and it makes it's a lot of fun because now like I have a group of people around me who like are all like really good at what they do and really understand what
they do and that that's kind of just an amazing amazing place to be I'm looking at this list and I just want to keep asking questions about it uh one of the principles that I love is it reminds me of Amazon has the same principle I believe which is leaders are right a lot yeah why do you find that to be
important I know you weren't necessarily designing all these principles but I imagine that something that you guys follow often and comes up a lot I mean this is one of my favorite ones because I think for particularly for a product org right because product leaders have to be right most of the time
because their decisions reflect across the entire org and their decisions fundamentally spend time right and they spend energy and if they make good ones the company does really well and if they make bad ones the company doesn't and one of the things I really value in product leaders are people who can go
into like an ambiguous information with an ambiguous situation with incomplete information and like a complex decision space and can like look at that and listen to everybody and read whatever they need to read and say this is where we need to go and like even if everyone else is like
ah I don't know that feels wrong for this reason this reason if they have like the confidence to like make that call and then a year later when you look back on it for them to have been right that's extremely valuable and it's one of these things that like it's really hard to test for right you can you can
get it by like talking with people and and asking hey was this person like usually right and respect people think about it but like in the context of like a given company just you have to take the time and see if those decisions are are largely right and it's the one value we have it's like you can't really learn
it right either either you're really really good at making those kinds of decisions or you're not right it's a very peculiar skill that we that we really value awesome shifting a little bit I know you all are going through this Global expansion we talked about this a little bit yeah and so just a few
questions along the lines because a lot of companies start you know one country most companies do and then they decide let's expand to New Markets so I guess first question is just how do you decide which markets to go after and specifically where to start first and then just prioritizing the list of
markets what's kind of your your algorithm for that so it starts with an assumption that we're going to have to be everywhere ultimately right that um you don't actually have to build like native Global payroll in every country in the world doesn't make sense to do that in every country in the world but
you definitely want to be able to pay people in any country in the world and you want to be able to have contractors anywhere in the world and have their information be in your HRS anywhere in the world and so the decision for us we were fortunate to or when we made that
decision to have quite a few customers already like thousand thousands of customers and so we knew not only where they're kind of U.S employees were but by virtue of being an employee system work we actually knew would have had other employees and so it was quite easy for us to say focusing on us-based
companies which is incomplete data right but if we just look at our us-based companies we know that there is immediate demand for those people to pay people in you know countries X Y and Z and we just like listed those out in raw numerical order and then we kind of looked at okay how hard is it to build
in these countries and how valuable is it to build in these countries right like what is the Strategic value of building in the UK or Canada or Germany or India or wherever and then as we had a discussion on like where is there risk right or where where is this where is this hard where is there a long Pole
where does this like in what countries does it take like a long time to get approval or whatever and we just stack rank them and uh and then we Revisited that decision right right like the early decisions that we made on exactly which countries like we have subsequently like reordered those over time and as we've
dived into countries and learned more you know we we rejigger things like a little bit but for the most part like that same basic list we started with is still like you know mostly right okay and then the other question a lot of Founders always struggle with is when is the time to start expanding
internationally because you know there's pros and cons do you have a sense of what convinced you all to start going International I think our case is slightly special but I think the right answer to that question is always before you think you do before you think you need to because like 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's a u in color right just as we care if there's not a u in color right there's like all of these subtle lessons that like
cultural lessons for companies that take like a really really long time to absorb and so my view is the always should do it earlier than you think you should that then you think you have to in our case it was always something we knew we had to do in fact we have a very clear
thesis that companies that aren't Global particularly in payroll but also in kind of insurance and benefits and I.T if you're not Global you're just not going to be around in 10 years because companies were becoming global and then covet 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 which became commonplace for small companies to be multi-country and so that very much um accelerated kind of our our timetable and then you saw it you know other people noticed that too and you saw
other companies starting to try to address parts of this problem as well and so there's this kind of competitive Dimension which is sort of secondary in in most ways because we were going to do it anyway but like that also kind of adds a little bit of a you know fire under the under the thing
what have you found to be most surprising about expanding internationally to be successful in in expansion for folks that are maybe starting down this road of like oh shoot we should think about that I think the thing that was most surprising to me the first time I did this back at guidewire in the in the OTS and Remains
the most surprising thing to most people you know every time I do this again is that every country is unique you can't just like you can't just take your us-based approach and like Drop it into another country other countries find it insulting it doesn't matter how much success you've had here everyone always
believes rightly or wrongly that their local context is special and you have to respect that and it comes down to like little things like there being a you in color or not or you know if you ever see a demo delivered to somebody in another country where they see like a detail
screen about a person that includes a social security number it's like that you immediately lose credibility doesn't matter how good all the rest of your stuff is and so I think that that is consistently the thing that I think is most surprising people is the degree to which that's true which seems obvious in
retrospect right if you took like German system or something and like demoed it in the United States with like poorly translated stuff we would think it would suck too right and so but it's not it's really hard to adapt to that mindset and um and so it takes just a lot of energy to to kind of overcome
that organizationally makes tons of sense I'm going to go in a different direction now um Frameworks so I know that you're not a huge fan of Frameworks we were chatting about this before we started recording and so I'm curious just to hear your perspective on why you're maybe not a fan of Frameworks and then
also just like how you crystallize processes and concepts for your team if you're not just like here's a framework you should use look I think Frameworks are very helpful so I'm not exactly anti-framework but I am anti-process as a substitution for deep product thinking right so I like to have just enough
process to create a frame right so that the right decisions can happen and like no more I think there's a danger especially as companies scale that you end up saying well you know if only we categorize you know everything correctly and jira like you know we will be able to make like really good prioritization
decisions so I'm like sure extremely helpful to have clear categorization and things in jurors and have like data and Analysis and to be able to do all of that stuff but what you really need to do is decide what's important to build right and then like have a way to build
it like really efficiently and so so I think the right answer the right amount of process for any given team is like the right frame for anything it's really just dependent on like their specific life cycle so you won't see me saying like oh we need to use like 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 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 of the quarterly planning process and two like everything does need in fact to be Endura because otherwise you can't rationalize about what's actually getting done and not is there a process or framework that you find is like counterproductive that you're just like
stay away from this thing uh we've had a lot of trouble with it or or generally it's like let's just rethink everything ourselves um no I don't find one to be particular I don't I haven't consistently found one to be particularly problematic so I think any framework sort of has its place you know right place right time I
think there's I think there's danger any one time that somebody like dogmatically says I think we should use process X because that's almost never the right answer in my in my experience I think I think there are places where that can differ like you start a company like on the basis of process X and like
everyone's bought into that process and everyone understands it um I think they can be really really great and like and on the engineering side I think this is hugely valuable it's like test driven development first line of code it's 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 if you had to compare the way coinbase builds products process wise or just product development process wise to Rippling what would you say are the bigger differences I think the differences are largely born of like the
different domains right so crypto as we talked about earlier really hard to predict what's going on there's all these questions about what's the future of crypto what's going to matter like what do we even need to build what's going to survive and so the process we had a coin is around like having those
debates and like getting to a decision and disagreeing committing and then from an execution point of view being able to move fast like that was the trick right at coinbase here we know the things that we need to build like at a high level and the trick is how do we really differentiate it on the
basis of like these amazing platform capabilities we have or how do we have to evolve those platform capabilities um in order to continue to build something that's just discontinuously better than everything that's out there and that like yields a different decision-making process 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 in the actual um making of the software what is that actual difference do you find like day to day is it like timeline differences is it how quickly I don't know the way
you structure how far you plan what do you find is like the concrete difference as a result I think the difference is in the day-to-day velocity of like decision making right because we can you know Rippling if you're like on I don't know pick a random team 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 you know whether you know Mac or Windows is going to exist in the future like none of there's none of that cognitive dissonance right there is we need to build this it's hard to figure out how we need to build this right because
there's all these different things that we could leverage but but we need to basically get this done and so the the kind of total velocity I would say is is higher here which does not say people work harder or less our Columbia is like Columbia's was like an amazingly fast like environment but it was also subject
to the fact that like you just don't know what the crypto markets are going to do and you have to be incredibly reactive to that and so I think maybe that's the one thing like the reactivity to like the environment in the crypto environment what's going on and the the uncertainty of the regulatory
environment all that stuff yeah really really really good at handling those things really rapidly which is something that we need to handle somewhat less um sounds quite stressful uh yeah I mean it was um it was fun like I stress yes it was stressful I mean every job I've ever had
has been stressful but in in its own unique way but all of that stress I think is in the shape of a problem that's in the context of a problem that's really interesting I mean that's why I stayed at these places right and so um but yeah it's stressful I'm looking back what a joy yeah no they
are very good memories like I look back I don't really I remember the stress but I don't like re-experience it right I remember like you know foraging these relationships and building these amazing products that that have been so lucky to be a part of and um and so I have you know almost only good memories of other
places I've been that's what I find too you go through these hard trips uh and then you look back and you're like wow that was so cool but assuming they go well assuming the company works out and like it feels like you know it was successful a lot of times you're a startup your life sucks for two years
and it doesn't work out in that there is a lot of you know upside and good memories to that but it's let's it's less less glorious yeah that's fair um though I mean the the first company I was really at kind of out of schools company called reactivity back in Internet one era and like we were trying
to figure out like how does this internet thing work how we start company is on the basis of these new technologies how do we help other companies like build stuff and figure it out you know in that company like fundamentally like didn't work out um ultimately God kind of Spun itself
out and got acquired uh which which was great um but like it was this extraordinary set of people that I was so lucky to work with and I you know I loved all the time I spent there and it was foundational to like everything else I ever did and so even though that effort didn't like you know pay off in the
traditional set like the value of the learnings I had there and then the people I had a chance to work with was just really exceptional so I feel very lucky that's a really good point actually and I think I should correct even what I said that even when things don't like work out traditionally those experiences
end up being incredibly valuable in all these unexpected ways yeah 100 yeah okay so the final topic I want to talk about hiring hiring product managers and interviewing yeah so you've hired a lot of PMS over the years I'm curious what's something you've learned about what to look for in product managers and also
just in product leaders that other people may not be focused on as you know like I mean I don't know that I have any like particularly special Insight here I I think there's a couple things that I do ask that I that maybe are more of an emphasis because it's Rippling than than
not but like the first of those is when people are kind of going through our process there's a part where they they do this case study and an important part of the case study is that it's like actually too complex for people to like have all of the answers up front there's just like the space of the problem is is
too large to do that which means that like in the interview there's a lot of opportunities or in the case study there's a lot of opportunities so just like ask ad-hoc questions or to like change one assumption and seeing how people react to that is really indicative of How Deeply they understand
you know a new problem or how quickly or how mentally agile they are and you know some people are extremely good at that like hearing 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 get like really
flummoxed right I mean obviously for our environment that former is like really really um important to us I think the other thing that really matters to me is like the insightfulness of the questions that people ask which is indicative of number one they're like actual interest in the job
right like people tend to ask better questions when they're like more excited about working at a place and like done their research and are asking people about it and also like the quality of those questions like can vary quite dramatically and and that's okay I don't expect quality to be the same all time
but like sometimes people ask a question like oh man I would have never thought to ask that question that's such an insightful question and then I pause and I have to think about my answer a little bit and so it kind of pushes me to be a little bit better um and when that happens I know I usually a pretty good candidate on my
hands is there an example of someone asking a really good question like that that comes to mind that you think back to and like oh wow that was great I remember about three years ago I was interviewing a guy named Kyle Boston and Kyle uh is now now runs our platform product organization and I can't
remember the specific question he asked but it had something to do with wait a minute if you have all these products and you have this like employee system of record thing underneath it shouldn't we be thinking about like how to create these like various pillars of kind of underlying platform technology
things like permissioning all this stuff and this was before we like fully formalized the concept of our like platform beyond the kind of employee systemic record and I remember thinking like yes yes we should and you know that had entered our minds before but the fact that somebody which who had like
almost no context on the company right that that's what was impressive about this question it's like man you've been thinking about Rippling for like a couple weeks while you're like interviewing with a bunch of other companies or whatever and like you've thought about it deeply enough to have
this insight into the nature of the platform that we're building like immediately like gave me a bunch of confidence and in his ability to kind of think through the sorts of things we need him to think through and I think it touches on PM's need to be Business Leaders and yeah great questions are
often about the business and the future of the business and how to make it run more efficiently and listen you know there's like a product org element to it but I find that that's like a really under appreciate element of PM series just like thinking about the bigger business not just like the PM product
yeah for me it's like two things it's like thinking about the bigger business right having having the context like around you know whether it's like Revenue questions or strategy questions but also like the detailed questions right it's like oh wait a minute the implication of this thing that I'm
getting asked or of this thing Jeremy that you said earlier is all of these things right and their ability to kind of understand that that that this isn't a simple business right it's really hard it's really complex and the ability to kind of to have these insights help them
think through those details is really cool you talked about this prompt they you give product managers not the giveaway 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 like a good example of a type of prompt to give a product manager candidate
in terms of like a general kind of approach I think a prompt should always like reflect the actual business that they're going to kind of come into right so so when we do like so our process overall is is actually quite short it's basically you know get in contact with us somehow eventually get you know
connected with a hiring manager have a conversation with them then more or less you have a conversation with me which is a product discussion and then we have a case study which follows that that's the whole process you know modulo other conversations around the edges and the questions that matter are around
like how do people think through that product discussion right which is relevant to our business how do people think through that case study that's number one and the second thing is there's always a part of my interview which is which is uh maybe sounds very simple but it's just like hey what
questions do you have for me right we actually do that before we do the product discussion and that's an incredibly important question because because it is again indicative of like these things that people have thought through or not thought through or kind of the depth of their thinking or their
interest and engagement in the role and like at that second discussion it doesn't have to be like perfect or anything but but it is a very strong signal when people you know whether they've thought through a set of questions they want to ask or just like you know on the Fly Like generating them
you learn a lot about how people think about product about you know what they're looking for about you know what they like doing and not doing just through those questions 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 be humble being a product person means that like by definition you're living in a world where like no one knows the right answer yet because if somebody did they would have already built it right and so having like no matter how smart you are 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 acknowledgment 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 the stuff and coming to different conclusions and so I found that that humility is one of like the biggest differentiators in early career product leaders who sort of are you know able to let go of like how awesome they were in school or in their first job or whatever I mean I had to do this and and
like and realize like the job is always hard and the job is always about Discovery every single day and if you can maintain that like curiosity and elasticity of thought and and creativity and light coming Solutions can be awesome but if you close after that and think you always have the right answer
then there's like no hope this touches on another principle that I still have sitting on my screen here which is uh great leaders change their minds a lot or just change their minds yeah willing to look at new information and say my mental model is adjusted by that or I was wrong
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 you write a lot but everyone's wrong sometimes right and and being in be able to be environment where you can just like say yep I was wrong
here's the way in which I was wrong let's move on is incredibly powerful final question you've brought up Parker a number of times and something that is clear about him is that he's a very product minded founder he has a lot of strong opinions about what products should be and as a product leader with a
Founder like that uh is often a challenging place to be similar to being the first piano 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 production
yeah no it's a great it's a great question so I think you got to be adaptable right like it's like any other relationship right you have to understand like what the nature of that relationship is where that person's going to care where you're going to Care the ways in which you can challenge each other
um like I think fundamentally you need to make sure that person is willing to be challenged right so you know I've seen product leaders or CEOs who are like kind of unwilling to be challenged and I wouldn't be able to work with those people um uh but but yeah Parker is uh incredibly strongly opinionated but he's
also incredibly informed which makes for some really really great debates and I've just found that like whatever is not even a CEO but whatever a manager's idiosyncrasies are you have to find a way to like work with those I think that that adaptability like I'm just sort of I like being like you know
a moldable puzzle piece where I can just kind of fit in um I think that's actually one of my one of my core skills so and so that's worked that's worked out for me and you know Parker and I before I started you know started developing like a deep Foundation of respect which is like
extremely important to like building that and like over the years it's just gotten deeper and deeper and um you know we don't always agree but like when we don't we can have a totally reasonable discussion about it and um and that's what makes it fun adaptability actually is I took a strength binder test once of
finding my own strings and that was my number one strength is I'm a deaf I think we share that that's excellent yeah seems like an important attribute for uh being in a place you're in well with that we've reached our very exciting lightning round I've got six questions for you if you're right all
right I'm ready hit me know what are two or three books that you've recommended most to other people well first is like my favorite series of books ever which is the Baroque cycle by Neil Stevenson uh it's a nine volume epic or three three volume nine book epic depending how you want to look at it but like it's
about the time like just before and like into the the enlightenment historical fiction a lot of fun and I also love uh the culture series by Ian Banks um which is just like super fun far future sort of uh uh universe so that I that I've really enjoyed what's a favorite recent movie or TV show watch
The Last of Us um it was an avid fan of the game and I thought they did a really really nice adaptation um favorite like I guess recent movies not that recent but I really like tenet yeah I wish which I thought was uh uh I'm I'm I was impressed with their ability to kind of go there and make
that movie and I just really enjoyed it like end to end we had a it kind of ended but we had a drinking game anytime someone mentioned last of us which uh took over the White Lotus I'm gonna drink some tea right here okay fair enough I'll try I've only got water normally I got tea but uh water today it
works uh but it's interesting it hasn't come up often so I think maybe we end that for now and see what the new pattern emerges yeah and then tenant feels like I was just thinking it feels like a compound movie compound startup as a movie a movie is very complicated too too yeah because I enjoyed it I
liked I like trying to like figure out like the multi timeline chart in my head as the movie can progressed the puzzle piece within you trying to find all the puzzle pieces yeah for sure what is a favorite interview question you'd like to ask you already maybe answer this but anything else comes to mind I think I
did no my favorite one is like what questions do you have for me but by far great what are some favorite products you've recently discovered that you love I guess I'll just mention I don't know if it goes as far as Holly's favorite products but there's two that come to mind my wife's computer
um 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 motherboards 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 and had to do like some really quick research and to buy new favorite pair of headphones and these focal bathies are like super nice I'm a bit of an audiophile I like to listen to like classical music and ambient stuff so we need a lot of dynamic range and these and you know
noise cancellation of these have been like great so far okay so what is it what are they called focal I think it's bath is b-a-t-h-y-s okay and is there a specific model or there's like that one that's it okay you'll you'll you'll know when you see it okay we will link to that in show notes so maybe I'll get one
what's something relatively minor you've changed in the way that you build product that has had a lot of impact on your team's ability to execute maybe the most recent Innovation sort of at Rippling was the kind of introduction of what I'm calling imperatives these things that whether they come bottom up
or top down are things that like everybody across the entire product and engineering team needs to do and what's important about that list is the things that are not on it and in a world where you know we could choose to do hundreds of things at once like being able to to kind of Force rank that list of things
draw lines like these are the ones everyone has to do has created a lot more focus and Clarity than than we had before so imperatives are essentially like here's the priorities for the next say quarter six months here the these here are the priorities for everybody and now integrate that into your own team's
priorities right so so each team like still is building like their own priorities but like have to factor in like this set how many of those do you usually have this is awesome I like this tip it it depends like it depends on what level of granularity you want to talk about them
at like like maybe 10 right it's a lot we're going through like between like globalization and like large improvements of the platform and like a bunch of other you know you know large companies all these things it creates a bunch of things that just have to be cross-team simultaneously I think it's
pretty natural part of a company's Evolution and we're just in that part of the cycle so awesome final question what's the question I should have asked you that I didn't ask you I guess what do I do with my kids maybe I have two kids six what do I do with my kids um my son I'm a big board gamer and
while I didn't push it on him my son he will play board games you know morning tonight and so we play a lot of like European like strategy games uh together and my daughter's now getting old enough that she's getting into them too and so uh we just finished as a family playing uh pandemic Legacy and the reward
tomorrow night is we get to start playing gloomhaven so that's gonna be fun I don't know either game sounds very hard and complicated they're fun they're fun amazing Jeremy we covered a lot of topics I feel like this is a compound podcast episode and so uh thank you for spending time with me thanks for being
here two final questions where can folks finding online if they want to reach out learn more and how can listeners be useful to you awesome LinkedIn is the easiest way online and uh you know if what I've been talking about today sounds interesting to you we're definitely hiring like senior
entrepreneurial PMs and so if those leadership principles on our website look interesting I'd love to hear from you what's the best way to explore those roles and apply the website has by far the best Channel it gets to this right recruiter who will tell me about it right Away Great so rippling.com and
there's probably a site for careers there's a career site on there that they're pretty easy to find we'll link to that in the show notes Jeremy thank you again for being here thanks so much for having me this was a lot of fun bye 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 leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lennyspodcast.com see you in the next episode