The Exchanges

Q Rippling is one of my favorite examples of, like, software companies that I think are very durable to, um, everything that's happening with AI. Does it change anything about your strategy, fundamentally?

A It definitely, um, makes us a lot more focused on data, um, like a lot of other companies, obviously, and, and capabilities around data. What I think is going to be very durable with, with AI is, like, everything that I've seen is, like, building the, the applications is, like, uh, I mean, I don't want to say it's, like, trivial, obviously everything's hard, but what's much harder than building AI applications are building, You know, governance and permissions and data pipelines and things like that. Um, and so, you know, that those are the areas like, you know, that we spend a lot of time on because they, they tend, they tend to be like our core strengths, particularly because like permissions and governance are very tied to an understanding of the work, you know, understanding, you know, usually permissions are about job and role and function. And or chart relationships. And so if you understand that deeply, you can be opinionated about who should have access to what, you know, who can do what in the system. And ultimately, I think like all of these AI agents are going to need to inherit the permissions of a person. Like some people would say, well, you know, maybe it can be like a service account that has distinct permissions. And the problem then is like, well, ultimately, like people are going to be interfacing with it. And if it has different permissions than they do, The…

AI assessment note: “It definitely, um, makes us a lot more focused on data”

Q How do you, I'm sure this has changed over time, but given platform and broad application surface area, like how do you organize at Rippling given you don't have like contemporary, many contemporary companies with a similar strategy? Um, and you can't be like, I'm going to do what Microsoft does at this scale.

A I mean, I think we try and, um, I mean, we have, we have teams that build capability. You know, that are kind of the, the platform teams. And then we have application teams that are building, you know, sort of hopefully out of the underlying platform capabilities applications. And I think it's like, it's really important to have like the right leader for these application teams. Like former founders are great. Um, but also you need people that can like scale over time, um, as, as the product grows. Um, and so I, you know, ideally, In an ideal world, you want someone with just like real ownership of those areas who can drive it because otherwise you get this, um, you get this sort of bottleneck at the level of executive attention where, you know, if I have to drive it, it's just like, I can't do that. I can only do that for so many things. And then inevitably a lot of balls get dropped. And so you need people like in seat who can like really own it and run like the business holistically, who can think about the product roadmap, the marketing, Um, you know, the sales elements, you know, the competition, you know, like the whole thing and kind of, you know, and synthesize it down to like, okay, here's what we're going to do. Um, and that's, that's always sort of the most challenging thing is to find those people. I mean, we, we try and hire a lot of founders at Ripley to make it w…

AI assessment note: “we have teams that build capability... platform teams. And then we have application teams”

Q maybe a year back and you told me that you were, uh, hopefully this is okay to say, you told me you were worried you weren't angry enough anymore to make rippling as successful as it should be. And I just burst out like fucking laughing and said like, well, like, My friend, don't worry about this. No one else is worried. Um, do you think being angry is important?

A I don't know if being angry is important, but I think that there were, at least in the, in early on, for the first couple of years at Ripley, um, this sort of like, um, for me personally, um, this sort of idea that this was like the only way, and this was the only thing, and like this, this sort of focus of that, um, You know, it was the first thing I thought about every morning when I got out of bed, and it was the last thing that I thought about when I went to sleep, and it was the thing that got me up in the middle of the night, you know, and, and I, I think that that was extremely motivating, like not, maybe not like super healthy. It sort of got me through a bunch of like difficult years and a, and a bunch of, a bunch of sort of grind, because it is a grind for a number of years, and I think like since then, Um, I don't remember this conversation, by the way, but I think, you know, since then, like, there are a lot of other, like, motivations, you know, that are, that are there. Like, I, I really love the product that we're building. I really like the people, um, that I work with. So there's a lot that I enjoy about work. There are a lot of other, sort of, like, positive motivations. Um, um, but yeah, you know, the nature of, like, some of that other stuff is it, it starts to kind of fade over time. You know, that's just the reality.

AI assessment note: “I don't know if being angry is important, but I think that there were”

Q real office or the first office, but he was just like, yeah, this is like, we're going to do Salesforce. And I'm like, Salesforce took a long time to get there. And he's like, we're going to do it all now. Um, do you, I'm trying to remember who this was. Do you, do you, uh, feel like the ambition is the same, or is changing ambition part of that?

A We've probably gotten better at articulating, like, sort of how we think about it, and so it started out with just this, like, this belief that, like, actually, you know, all, all of this, these ideas that people had that the way to build great products were to, like, focus, you know, really narrowly was wrong. Um, and that actually the, the right path was to try and build, um, like a coherent product suite, um, of seamlessly integrated and, and interoperable applications. At first it was just like, no, no, no, we're going to do like HR and IT. And there are these other things on the roadmap, like, you know, sort of finance and stuff like that. Um, and I think over time, uh, we, we probably got like a little bit better at articulating sort of why that Why that was. And I think the, the best way to express it is that I think that what, what people get wrong about software is historically, we've been building software in this way, where if you, you focus really, really narrowly on a very specific domain or application area, um, and people think that you can sort of craft these artisanal products and experiences that way. The problem that you run into is that ultimately companies end up having a lot of different applications and that creates a lot of problems for them. But also these artisanal software companies really can't afford to invest in a set of underlying capabilities tha…

AI assessment note: “We've probably gotten better at articulating, like, sort of how we think about it”

Q Rippling. I mean, we've been talking about a bunch of principles that are very specific to To rippling doing its own thing versus listening to conventional wisdom. How much do you think about beating incumbents and HCM or payroll or identity or whatever it is versus capturing Greenfield and like your strategy internally?

A The two things are related. Like a lot of the time, you know, we can, we can, we can beat incumbents because of the, the sort of we've, we've sort of pushed the envelope a little bit into new horizons. And so that allows us to solve Problems for customers that incumbents can't solve. Um, and even, like, sometimes, like, it's, like, not always clear to me internally, like, what the difference is for customers between, like, new applications versus existing, you know, and, like, new features versus bug fixes. Like, a lot of times, like, whether we categorize something as, like, a fix or, like, a new thing is about whether we internally Believed that this capability was part of like the original spec. But from the customer's perspective, it's always just like, I wish it did this thing and it doesn't do it. Um, you know, so to them, like everything's a bug. We're building a variable compensation product right now. And like, In some sense, it's a new thing. It's a new application, new skew, but it also like, you know, really helps, um, you know, if you're, if you're an existing customer, it's an existing problem that you have.

AI assessment note: “The two things are related. Like a lot of the time, you know, we can beat incumbents”

Q I don't know a single founder who doesn't feel like they could use more owners at their own company. Like, do you, um, do you have any advice on how you filter for this?

A No, in terms of filtering, I think it's hard. Like people who have had that experience before, um, I think it's, uh, sometimes it just, you know, having a conversation with someone, you know, are they kind of naturally, you know, jumping to, you know, sort of conclusions and implications about the business and kind of getting there on their own? Or, you know, how much do you kind of need to lead them there? It's hard. And I think the difference is like, it sort of comes out in, um, in like planning, in like quarterly planning. Like some people show up to quarterly planning and there's like, there's a list of they're like, here are the things that we kind of need to get done from a product perspective. And the list inevitably sort of like, you know, you unfurl it and it kind of goes like down the hallway. And, and some people are like, okay, well, you know, we're going to do about one quarter's worth of work. We've prioritized the list and one quarter's worth of work is like this much of the list. And that's what we're going to get done. That's my job. And The problem is it's like, now it's like my job to kind of make the ends meet. Cause like that part, that's not going to cut it. You know, it doesn't, you know, we actually have to get a lot more done to make things work. And so now it's, it's sort of my job to figure out like, how do we sort of bridge this gap? Um, and what yo…

AI assessment note: “in terms of filtering, I think it's hard. Like people who have had that experience”