How Rippling CEO Parker Conrad grew Rippling to $1B revenue and 2K customers in 2026.

you're gonna love this interview just got done editing it i'm glad i got it live for you i'll be in the comments for the next 30 minutes hanging out answering any questions you have in fact leave a comment below about data points or what you think is going to happen to the company and i will respond every comment additionally if you're just loving the content click the thumbs up and i will go and check out your profile as well and give your videos some love as well in the meantime enjoy the interview hello everyone my guest today is prasanna sankar he's building a very cool company called rippling which is playing in the all-in-one hr and it space he is the cto all right persona you ready to take us to the top yeah all right um so talk to us you know you come from the director of engineering role at zenifit so let's pick up there when did you leave benefits so i left right after parker left so you know when parker was fired from benefits i wrote him an email saying hey dude like you know i know you're going to start a company and i want to join you and parker was like no no i'm gonna you know i'm done um so that's sort of what kicked off you know the the rippling thing um after a month he was like yeah actually i'm starting a company so when what what company was that rippling oh got it got it very good so you guys are now working you're cranking together still today he's still active with the company yes very good he's the ceo so so walk us so how did you guys get connected so you were because you you kind of came from a competitive background you were number one uh an indian top code from a competitive programming perspective now how do you measure competitive programming is a number of code like lines written per minute or what um there are a bunch of online competitive you know contests that run um top coder is one google code jam is one um there is facebook runs some of those as well um and they have these algorithmic problems that you need to solve in a short period of time and you know they have a way to rank people so in those contests they'll rank one in india consistently for a while yep okay so i love this so you get to get so parker says hey is it gonna take a break i'm gonna take a break he lasts barely a year and he calls you up and goes all right barely a month he says persona i'm jumped back in so what year was that when did you guys write the first line of code for this uh 2016. okay 2016. and then when did you have your first dollar revenue do you remember quite a bit late i think 18 months out 18 months okay got it so you spent 18 months essentially building the product listen one of the things i always like to understand is how people approach building an mvp some people raise a ton and spend a ton without the first dollar revenue somebody will bootstrap to the first dollar so how much did you guys spend on the mvp 10 million dollars okay got it why what made it so expensive um it's just a large large build out i mean imagine if google sort of self-destructed and went under and you know bus went past there is a huge gap and void in the market that it leaves um so you know it involved uh building you know what zenefits would have built 10 years ahead so you know we had to build a large product to just even get started and what was your thesis in building the mvp what mousetrap were you building that you thought no one else had we clearly knew uh you know parker clearly has seen with like 50 million dollars worth of err um the needs of customers and you know they were asking for stuff that benefits did not have the bandwidth to build at all you know remember zenfits was growing insanely fast so you know we were completely focused on just servicing the existing products and you know on day one we had a clear road map of what the market really wanted and who were you so the product that you are building in the mvpn today describe the customer you're selling to your kind of sweet spot target customer our sweet spot customer is 5 200 employees in their company especially the ones that are growing fast which have a lot of changes that are constantly happening in the company that needs to be synced in all these business systems they're using so you know 500 companies fast growing and give me a sense of what they would pay so on average what's what's the rpu of customers paying you we are around i think 2015 to 20k per year but here yeah okay got it so this is caught 1500 to kind of 1800 per month kind of deals yeah yeah yeah okay and what are they deploying i mean as an engineer especially the one that helped build or really built the mvp you always like to see like okay we got a customer what's the first thing that they use did anything surprise you in terms of what you thought they would use versus what they're actually using um i mean i've been into several startups so far this one has been the least surprising this one has been you know the clearest roadmap that we've ever gotten uh we did have some surprises like you know uh we did have to make some changes um uh especially we thought we could sort of like get away without building the health insurance part uh but you know the competition was so intense that we had to sort of build it um you know every other player in the market was offering it so we had to build it so it took a bit of time to catch up to that but like largely it's been without surprises um you know parker sort of sat on day one and gave a four year six year road maps and you know we've largely been executing to that and you know most startups can't really say that i've never been able to say that in any of my other startups and how much capital did you guys raise on day one back in 2016 um day one parker put in you know half a million of his own money um and beyond that maybe in nine months we sort of raised around 10 million dollars which is what you spent on the mvp yeah a little more than 10 yeah yeah and today how much of your race total total maybe like uh you know 60 million or a little bit more than that 60 65 65 65 yeah yeah do you you know there are two kinds of people and i know there are very few founders that have done both there are a lot of founders that have bootstrapped a company to call not a lot but i know founders got a bootstrap to call it 30 40 50 million bucks an arr and there's others that just you know they're young they're hustlers they want a lot of risk so they say you know what we're going to go the vc route we're going to swing for the billion dollar offenses it's billion dollars or bust i kind of put you in that category is it accurate it's 100 billion or bust okay 100 x more aggressive than what i just said so i like that so how does your mind work on a daily basis to kind of kind of rationalize that that's what you're doing um i think you know it's a totally different ballgame it involves you know hiring the best that you can hire it involves understanding that you know people and the org needs to scale keep scaling and uh you know building technologies instead of people to do most functions which is what we sort of like learnt a lot from benefits this is failures how much how much of that upside you know when parker and you you know get back together in 2016 there's a conversation obviously about equity uh and equity splits relative to salary and upside and all that stuff and obviously you have vcs on the cap table as well at this point did you guys just do it easy do you split it 50 50 and then just take the delusion from vcs and go from there not really parker uh is owns more equity than i do we split at 60 40. okay that's good so 60 40 and then 10 million from vcs early on obviously dilutes you a little bit but there's still enough upside for you where you're happy to go on podcast and say we're 100 billion or bus because if that happens you're a billionaire yeah yeah yeah very good okay let's go back i always like to get that from a mindset perspective because it's a very different mindset to do what you're doing versus bootstrap to you know 10 20 million bucks and get rich off cash flow right there's not a right or wrong they're just different yeah so you launch in 2016 function of the market yeah yeah well tell me to go deeper there since you went there so what are you seeing in the market that tells you you can build a 100 billion dollar company in this kind of all-in-one hr space yeah i mean you know zenifits grew from zero to 50 million dollars in like less than two years uh in arr and you only sort of get that kind of growth by just like skimming the cream of the cream of the cream of the market right like you know it you know it's clearly signals insane market pull and huge demand for the product and it clearly signals you know potentially 100 billion company that could get created and if you look at all the huge companies that got created they had these kind of trajectories of growth rates and market pull which is what we've seen so you know it was very clear that you know this is a huge market with the winner take all dynamics you know especially um...