Founder Interview
How Rippling Reached 2,000 Paying Customers by 2019 (Interview with CTO Prasanna Sankar)
- Interview Date
- March 19, 2019
- Interviewee
- Prasanna SankarCo-Founder and CTO
Company Metrics at Interview Time
Customers (2019)
2,000 companies
Total Funding Raised (2019)
$61M or a bit more
Team Size (2019)
200 people
Engineers (2019)
100
Quota-Carrying Sales Reps (2019)
20
Historical Snapshot
These numbers were reported by Prasanna Sankar during the interview recorded in March 2019 and are a historical snapshot, not current figures. See Rippling’s current numbers.

Key Takeaways
- 01Rippling was founded in 2016 and spent 18 months building the product before earning its first dollar of revenue
- 02Parker Conrad put in $500,000 of his own money on day one, followed by a $10M raise roughly nine months later
- 03Total funding raised was $61M or a bit more as of March 2019
- 04The most recent raise was $45M from Kleiner Perkins in February 2018
- 05Net revenue retention was around 300% at the time of the Kleiner raise, driven by fast-growing customers adding seats
- 06Rippling had 2,000 paying companies as customers in 2019
- 07The team totaled 200 people, including 100 engineers and 20 quota-carrying sales reps
- 08CAC payback was about nine months in total; Prasanna said sales rep compensation alone was recouped in the first month
- 09Prasanna declined to share revenue and would say only that $36M in ARR, the figure the host had put to him, was not really far away, meaning Rippling had not yet reached it
- 10The founders split their equity 60% to Parker Conrad and 40% to Prasanna Sankar, before VC money diluted them
Company Metrics at Time of Interview
| Metric | Value | Source |
|---|---|---|
| Year Founded | 2016 | Interview, Mar 2019 |
| MVP Build Cost (2016) | $10M | Interview, Mar 2019 |
| Parker Conrad Personal Investment (2016) | $500,000 | Interview, Mar 2019 |
| Seed Funding Round (2016) | $10M | Interview, Mar 2019 |
| Kleiner Perkins Round (2018) | $45M | Interview, Mar 2019 |
| Total Funding Raised (2019) | $61M or a bit more | Interview, Mar 2019 |
| Customers (2019) | 2,000 companies | Interview, Mar 2019 |
| Average Contract Value (2019) | $15,000 to $20,000 per year | Interview, Mar 2019 |
| CAC Payback Period (2019) | 9 months | Interview, Mar 2019 |
| Net Revenue Retention at Kleiner Raise (2018) | About 300% | Interview, Mar 2019 |
| Team Size (2019) | 200 people | Interview, Mar 2019 |
| Engineers (2019) | 100 | Interview, Mar 2019 |
| Quota-Carrying Sales Reps (2019) | 20 | Interview, Mar 2019 |
| Runway Targeted at Last Raise (2018) | 30 months | Interview, Mar 2019 |
| Founding Equity Split (before VC dilution) – Parker Conrad | 60% | Interview, Mar 2019 |
| Founding Equity Split (before VC dilution) – Prasanna Sankar | 40% | Interview, Mar 2019 |
Growth Breakdown
Customers
Rippling had 2,000 paying companies as of March 2019, each defined as a unique company that pays. The average customer had roughly 30 employees, though Prasanna noted the company was attracting larger customers over time.
Revenue
Prasanna declined to share revenue: "I don't want to get into the revenue numbers yet, you know, because of the backlash." He rejected the host's run-rate estimate from multiplying 2,000 customers by the ACV, agreeing that the ACV was rising and that older cohorts had paid less. Pressed again, he would say only that $36M in ARR, the figure the host had put to him, was "not really far away", so Rippling had not reached it.
Team
The team totaled 200 people as of March 2019, including 100 engineers managed by Prasanna and 20 quota-carrying sales representatives following an inside sales playbook similar to Zenefits.
Funding and Runway
Rippling raised $45M from Kleiner Perkins in February 2018 and had raised $61M or a bit more in total by March 2019. Prasanna said the Kleiner round was raised to cover about 30 months of runway.
Growth Strategy
Cold Email Outreach for First 100 Customers
The first 100 customers were acquired primarily through cold email outreach targeting founders, CEOs, and CTOs. This direct approach gave Rippling its initial traction before expanding to other channels.
Multi-Channel Distribution via Value-Added Resellers
As the company scaled, Rippling leveraged accountants, insurance brokers, and IT admins as distribution channels. Prasanna said the company typically used all of these channels to its advantage.
Inside Sales Team
Rippling built a team of 20 quota-carrying sales reps following a playbook similar to Zenefits, with quota targets set at roughly five times full OTE and an SDR-to-AE-to-CSM flow.
Seat-Based Expansion Revenue
Net revenue retention was approximately 300% at the time of the Kleiner raise, driven mostly by organic seat additions as customers grew. Prasanna noted the company had not yet invested heavily in structured upsell motions.
All-in-One Product Positioning
Rather than starting with a narrow product and expanding, Rippling launched as a full all-in-one HR and IT platform from day one. Parker Conrad's roadmap, informed by his experience at Zenefits, gave the team a clear multi-year build plan that reduced surprises.
Best Quotes
“Day one Parker put in, you know, 500,000 of his own money. And beyond that, maybe in nine months, we sort of raised around $10,000,000.”
“Total maybe like, you know, 61,000,000 or a bit more than that.”
“It's a 100,000,000,000 or bust.”
“Not really. Parker owns more equity than I do. We split it sixty-forty.”
“Yeah, yeah, it is significantly greater than 100%. When we raised our last financing round from Kleiner, it was around 300% which was something abnormal. That was mostly because we were especially selling to fast growing companies so they grow. So it was abnormally high. Now as we sort of get the larger portion of the market, it is, you know, it is less impressive, but it's still pretty impressive.”
“You know, I think, you know, 36,000,000 in ARR is not really far away.”
“Actually, that's probably not true. It's our sales rep comp that we sort of recoup on the first month. So our total payback might be like, you know, nine months or something like that. So yeah.”
“Most of it has been seat upsells, which is automatic, right? Like we don't even put, we have not done historically a great job on upsell so far. Right now we're sort of investing more on that, but most of it is just like organic seat ads.”
What Happened Next
This interview captures Rippling at an early stage in March 2019, when the company had 2,000 paying customers and had raised $61M or a bit more in total. Prasanna Sankar declined to share revenue, saying only that $36M in ARR, the figure the host had put to him, was not really far away, and he called the company's ambition $100 billion or bust. Rippling has continued to grow significantly since this recording. Visit the Rippling company profile on GetLatka for current figures.
View Rippling’s current profile and metricsFull Transcript
Chapters
- 0:25Introduction and Prasanna's Background
- 0:47Leaving Zenefits and Starting Rippling with Parker Conrad
- 2:09First Line of Code and Time to First Revenue
- 2:25Building the MVP: Cost and Product Vision
- 5:32Early Funding: Parker's Personal Investment and Seed Round
- 5:50Total Capital Raised and VC Strategy
- 9:23Customer Acquisition Cost and Payback Period
- 11:51Customer Count and Revenue Discussion
- 16:32$36M ARR Not Far Away
- 17:00Go-to-Market Strategy and Distribution Channels
- 18:11Team Size: Engineers and Sales Reps
- 19:07Churn and Net Revenue Retention
- 20:44Kleiner Perkins Raise and Runway Planning
- 22:26Famous Five Rapid-Fire Questions
Nathan Latka
00:00You'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 thirty minutes hanging out answering any questions you have. In fact, leave a comment below about data points or what you think is gonna happen to the company, and I will respond to every comment. Additionally, if you're just loving the content, click the thumbs up, and I will go and check out your
00:18profile as well and give your videos some love as well. In the meantime, enjoy the interview.
Introduction and Prasanna's Background
Nathan Latka
00:25Hello, 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, Prasanna, you ready to take us to the top? Yeah. All right. So talk to us, you know, you come from the director of engineering role at Zenefits. So let's pick up there. When did you leave Zenefits?
Leaving Zenefits and Starting Rippling with Parker Conrad
Prasanna Sankar
00:47>> So I left right after Parker left. So, know, when Parker was fired from Zenefits, I wrote him an email saying, Hey dude, like, know, know you're going to start a company and I want to join you. And Parker was like, No, no, I'm going to, you know, I'm done. So that's sort of what kicked off, you know, the Rippling thing. After a month, he was like, yeah, actually I'm starting a company, so.
Nathan Latka
01:10When? What company was that?
Prasanna Sankar
01:12>> Rippling.
Nathan Latka
01:13Oh, it. Got it.
01:14Very good. So you guys are now working, you're cranking together still today? He's still active at the company?
Prasanna Sankar
01:18>> Yes.
Nathan Latka
01:18Very good.
Prasanna Sankar
01:19>> He's the CEO.
Nathan Latka
01:20So so walk us so how did you guys get connected? So you were because you you kinda came from a competitive background. You were number one in India on Topcoder from a competitive programming perspective. Now how do you measure competitive programming? Is it number of code, like lines written per minute or what?
Prasanna Sankar
01:37>> There are a bunch of online competitive contests that run. Topcoder is one, Google Code Jam is one, there is Facebook runs some of those as well. 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.
Nathan Latka
01:59Yep. Okay. So I love this. So you get to get, so Parker says, hey, I'm gonna take a break. I'm gonna take a break. He lasts barely a year and he calls you up and goes, right, Prasanna.
Prasanna Sankar
02:06>> Barely a month.
02:07>> Barely a Barely a month he says Prasanna.
First Line of Code and Time to First Revenue
Nathan Latka
02:09I'm jumping back in. So what year was that? When did you guys write the first line of code for this?
Prasanna Sankar
02:14>> 2016.
Nathan Latka
02:16Okay, 2016. And then when did you have your first dollar of revenue? Do you remember?
Prasanna Sankar
02:22>> Quite a bit late. I think eighteen months out.
Building the MVP: Cost and Product Vision
Nathan Latka
02:25Eighteen months. Okay, got it. So you spent eighteen months essentially building a 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. Some people bootstrap to the first dollar. So how much did you guys spend on the MVP?
Prasanna Sankar
02:39>> $10,000,000
Nathan Latka
02:40Okay. Got it. Why, what, what made it so expensive?
Prasanna Sankar
02:44>> It's just a large, large build out. I mean, if Google sort of self destructed and went under and, you know, went bust. There is a huge gap and wide in the market that it leaves. So, you know, it involved building what Zenefits would have built ten years ahead. So, you know, we had to build a large product to just even get started.
Nathan Latka
03:06And what was your thesis in building the MVP? What mousetrap were you building that you thought no one else had?
Prasanna Sankar
03:14>> We clearly knew, you know, Parker clearly has seen with like $50,000,000 worth of ARR the needs of customers. And, you know, they were asking for stuff that Zenefits did not have the bandwidth to build at all. You know, remember Zenefits 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 roadmap of what the market really wanted.
Nathan Latka
03:41And who were you, so the product that you guys building in the MVP end today, describe the customer you're selling to, your kind of sweet spot target customer.
Prasanna Sankar
03:50>> Our sweet spot customer is five to a 100 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, five to 100 companies fast growing.
Nathan Latka
04:10And give me a sense of what they would pay. So on average, what's the ARPU of customers paying you?
Prasanna Sankar
04:15>> We are around, I think 15 to 20 ks.
Nathan Latka
04:19Per year?
Prasanna Sankar
04:21>> Per year, yeah.
Nathan Latka
04:22Okay, got it. So this is called 1,500 to kind of $1,800 per month kind of deals?
Prasanna Sankar
04:27>> Yeah, yeah, yeah.
Nathan Latka
04:28Okay, and what are they deploying? I mean, as the 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? Anything surprise you in terms of what you thought they would use versus what they're actually using?
Prasanna Sankar
04:43>> 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. We did have some surprises like, you know, we did have to make some changes.
04:58>> Especially we thought we could sort of like get away without building the health insurance part. But you know, the competition was so intense that we had to sort of build it. 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. You know, Parker sort of sat on day one and gave a
05:18>> four year, six year roadmap. 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 the other startups.
Nathan Latka
05:27Yep, and how much capital did you guys raise on day one back in 2016?
Early Funding: Parker's Personal Investment and Seed Round
Prasanna Sankar
05:32>> Day one Parker put in, you know, 500,000 of his own money. And beyond that, maybe in nine months, we sort of raised around $10,000,000.
Nathan Latka
05:43Which is what you spent on the MVP?
Prasanna Sankar
05:45>> Yeah, a little more than 10. Yeah.
Nathan Latka
05:47Yeah. And today, how much have you raised total?
Total Capital Raised and VC Strategy
Prasanna Sankar
05:50>> Total maybe like, you know, 61,000,000 or a bit more than that.
Nathan Latka
05:5560,000,000? 65. 5. Yeah. Do 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 that have bootstrapped to call it $30,000,000, $40,000,000, $50,000,000 in ARR. And there's others that just you know, they're young, they're hustlers, they want a lot of risks. So they say, you know what? We're gonna
06:15go the VC route. We're gonna swing for the billion dollar fences. It's billion dollars or bust. I kind of put you in that category. Is it accurate?
Prasanna Sankar
06:21>> It's a 100,000,000,000 or bust.
Nathan Latka
06:24Okay. A 100 X more aggressive than what I just said. So I like that. So how does your mind work on a daily basis to of rationalize that that's what you're doing?
Prasanna Sankar
06:37>> I think, you know, it's a totally different ball game. 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, know, building technologies instead of people to do most functions, which is what we sort of like learned a lot from Zenefits, so it's failures.
Nathan Latka
06:56How much of that upside, you know, when Parker and you, you know, get back together in 2016, there's a conversation obviously about equity 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 fifty-fifty and then just take the dilution from VCs and go from there?
Prasanna Sankar
07:15>> Not really. Parker owns more equity than I do. We split it sixty-forty.
Nathan Latka
07:21Okay, that's good. So sixty-forty and then 10,000,000 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 podcasts and say we're going for a 100,000,000,000 or bust. Because if happens, you're a billionaire.
Prasanna Sankar
07:33>> Yeah. Yeah. Very good.
Nathan Latka
07:34Okay. Let's go back. I always like to get that from a mindset perspective because it's a very different mindset to what you're doing versus bootstrap to, you know, $10,000,000 to $20,000,000 bucks and get rich off cash flow. Right? There's not a right or wrong. They're just different.
Prasanna Sankar
07:46>> Yeah.
Nathan Latka
07:47So you launch in 2016. It's a function of the market.
07:49Yeah. Well tell me, go deeper there since you went there. So what are you seeing in the market that tells you you can build a $100,000,000,000 company in this kind of all in one HR space?
Prasanna Sankar
07:59>> Yeah, I mean you know Zenefits grew from zero to $50,000,000 in like less than two years 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, know, it, you know, it's clearly signals insane market pull and huge demand for the product. And it clearly signals, you know, potentially a $100,000,000,000 company that could get created. And if you look
08:22>> at all the huge companies that got created, they had these kinds of trajectories of growth rates and market pull, which is what we're seeing. So, you know, it was very clear that, you know, this is a huge market with the winner take all dynamics, you know, especially, you know, the ultimate players like an app store where any SaaS developer can sort of plug in, plug in and publish his app and, know, Rippling provision seats and licenses
08:51>> on top of this, you know, and provides distribution for these apps, right? So it is clearly a network effects business. It's a winner take all business. So, you know, it requires to be number one. It requires you to go for the number one.
Nathan Latka
09:04So as you're going for that number one spot, there's a lot of people that would argue and say whoever can pay the most for the customer, because their economics are strong, will win the customer. So you raise a lot of capital, you have a war chest, your average first year ACV is you said between 15 and $20,000. What do you spend on fully weighted CAC to get that customer?
Customer Acquisition Cost and Payback Period
Prasanna Sankar
09:23>> We almost sort of like, our payback is like, you know, is insanely profitable right now. It's like one to two months or something like that. So, you know, it's not true. That's not the game that we're playing, you know.
Nathan Latka
09:38So yeah, was gonna say that means you're spending $2,000 or $3,000 to get a $15,000 to $20,000 a year customer.
Prasanna Sankar
09:46>> Actually, that's probably not true. It's our sales rep comp that we sort of recoup on the first month. So our total payback might be like, you know, nine months or something like that. So yeah.
09:59>> So we're not in the business of like paying the most to get the customer at all. We are, you know, we are pretty unique. Nobody else has like what we have in terms of product breadth, You know, there is no competition in the market. You know, there is no one else out there going to the customers with the sales pitch that we are going with. We're just like we are an all in one solution. We are
10:22>> an operating system to run your company. So, you know, we are pretty differentiated on that.
Nathan Latka
10:28Well, there's a lot to be fair. There are a lot of companies where the prize is the same, a $100,000,000,000 HR tech kind of store company, but the mousetrap they're using to get there is different. So they today would not describe themselves as all in one. They would say we do this specific thing very well and they're getting a lot of traction there and they will expand to become all in one. Why have you chosen to
10:48basically say, fuck it. We're just going to say we're the all in one thing. We're not going to say we're a mousetrap and we're the best of this one thing. We're just going we're the best for all of it.
Prasanna Sankar
10:55>> It's usually easier to get there that way.
10:59>> What we've seen, you know, from Zenefits and you know, in any of the other hyper growth companies that I've been at is once you get insane level of traction and market pull, you know, things are compounding at a really huge rate that you're just like struggling to keep up with the existing product breaking. And you're just like constantly patching and fixing that. And you know, my hypothesis is that, you know, if you need to create a
11:23>> large hyper growth company, whatever you built in the first like eighteen months or something is sort of the extent to which you're going to build in the life cycle of your company. And we've seen that at Zenefits where we unsuccessfully tried to enter into new markets and, you know, failed continually.
Nathan Latka
11:40Well, okay. So let's we'll go back to that in a second. But so for Rippling between 2016 to 2017, you know, you spend $10,000,000 MVP, your first dollar revenue in 2017. How many customers have you scaled to now today?
Customer Count and Revenue Discussion
Prasanna Sankar
11:51>> We have around, you know, 2,000 or more than that customers.
Nathan Latka
11:55Okay.
Prasanna Sankar
11:56>> 2,000, 5,000 somewhere.
Nathan Latka
11:57And how you define a customer?
Prasanna Sankar
12:00>> Someone who pays.
Nathan Latka
12:02Okay. But is it in other words, is that 2,000 companies that pay you or that's the number of seats per a smaller number It's of
Prasanna Sankar
12:10>> 2,000 companies that pay us.
Nathan Latka
12:11I see. Okay. And about how many seats is that?
Prasanna Sankar
12:15>> I'm not sure. I think our average customer would probably have 30 employees, but I could be totally wrong in the ballpark. We've been sort of attracting larger and larger companies as time goes by, so, you know, my estimate could be really off.
Nathan Latka
12:34Yep. Yep. Yep. Well, mean, if we take 2,000 customers times that ACV target you told me earlier, that would put you at about $3,000,000 a month right now in terms of run rate. Is that ballpark accurate?
Prasanna Sankar
12:45>> I don't think that's accurate. There is something missing in that matter, but, you know, I don't think that's accurate.
Nathan Latka
12:49Which of those two numbers is off? So you said earlier $20,000 ACV, and you just said 2,000 customers. Those multiplied would put you at a 3,000,000 run rate
Prasanna Sankar
12:59>> or MRR. Yeah, yeah, I'm not sure. I don't want to get into the revenue numbers yet, you know, because of the backlash. You know, we're sort of like pretty coy about the revenue numbers because, you know, Zenefits had a lot of coverage around that and, you know, it sort of anchors us out there. So we're sort of like not really talking about the revenue numbers, but you know, I can tell you that it is sort of
13:22>> the fastest growing company that I've kind of like seen, you know, we've kept it under the radar. You know, it's sort of like at Slack kind of growth rates.
Nathan Latka
13:32Well, Prasanna, so just to be clear, get people that come on all the time that raise a lot of capital. They're burning like you wouldn't believe. They say they're the fastest growing. And when you try and get quantification, they go, Oh,
13:44we're not talking about it. And usually it's bullshit. Right? So when I'm looking at, when I'm looking, I never want to bring out a revenue number unless the guests, in this case, you provides the data for me to get to that number. So, you know, we have a very sophisticated SaaS audience, very smart people listen, 10,000,000 downloads. They will take 2,000 customers times an ARPU to get MRR. That's how the math works. So I just want
14:11to give you one second to potentially correct either of those numbers because that's what's going to happen. They're going to multiply that ACV you said times 2,000 customers and back into 3,000,000 a month in revenue.
Prasanna Sankar
14:21>> What I would say is all these numbers are shifting really fast. You know, the ACV is growing really fast.
Nathan Latka
14:26No, but we talked about ARPU though. ARPU is average revenue per user per month.
14:32So is what you're saying basically, by the way we can move on from this if you can just I just want to quantify this to put an end on this part of the story right. What I hear you saying is you're moving upstream which means your new ACV today might be $20,000 ACV's but you might have historical cohorts that paid less than that. So you can't just multiply 20,000 times 2,000 customers to get a $36,000,000 run
14:56rate today.
Prasanna Sankar
14:57>> That's correct.
Nathan Latka
14:58I see. Okay, cool. I think that's a good kind of close off to that story. So the lessons there is you start off with again, potentially lesser value cohorts, smaller team sizes, then now the average team is 30 people, 20,000 ACVs, you're scaling and today you have 2,000 paying customers. Yeah. Now is a $30,000,000 run rate you know, in your sites in the next twelve to twenty four months, or do you think you need more time
15:21to get there?
Prasanna Sankar
15:24>> I'm gonna decline on that one. You know, I I don't know. I mean, yeah, don't know how answer that one.
Nathan Latka
15:31Okay. Why do you decline that? But then two minutes prior you say we're the fastest growing company, it's hyper scale, it's hyper growth, it's the best we've ever seen. It seems those are at very opposite ends of the spectrum.
Prasanna Sankar
15:42>> We don't want to talk about, you know, revenue numbers and anchors out there, But, you know, I can tell you that, you know, it's sort of like kind of, you know, the space at which the company is growing, I've never seen it's incredible. So I can tell you that.
Nathan Latka
15:58Yeah, but going from a dollar a year to a thousand dollars a year in revenue is incredible growth rate. It means nothing.
Prasanna Sankar
16:05>> I understand.
Nathan Latka
16:07Understand. I'm asking these questions to try and help you fill out the story. And so it's less vague, not more vague. That's the only reason I'm continuing to ask you these questions. So you can keep saying best growth all you want, but my audience, again, they're smart. They're going to listen to that and go, something's fishy here. I just want to give you any opening you want to clarify anything.
$36M ARR Not Far Away
Prasanna Sankar
16:32>> You know, I think, you know, 36,000,000 in ARR is not really far away.
Nathan Latka
16:39Fair. Okay. That's a good end. That's a good end to that part of the story. So let's move on. That's good. Where are you getting most of growth? So Zenefits famously gotten to all kinds of hot water because of really it was the market motion. Do you work with the providers? Are you a broker? Are you not a broker? So what's the go to market strategy for Rippling?
Go-to-Market Strategy and Distribution Channels
Prasanna Sankar
17:00>> So Rippling is an all in one product, right? So we have a payroll system, we have an insurance product, we have the HR product and so on. So we use all these different channels to distribute the product today. So, you know, we could go and sell to accountants, we could go and sell through insurance brokers, and we could go and sell through, you know, IT admins. And we use, we typically use all of them to our
17:23>> advantage, which gives us some level of vitality as well.
Nathan Latka
17:28So just just to be I mean, let me let me go back to the roots then. The first 100 customers you signed up, how did you sign? What channel did you mainly rely on to get the first 100?
Prasanna Sankar
17:36>> Email. Mostly email.
Nathan Latka
17:38Okay. Tell me more about that. Like cold outreach?
Prasanna Sankar
17:40>> Cold Outreach, yep.
Nathan Latka
17:42Wow. Okay. What, I mean, how did you find your email and what job title were you targeting?
Prasanna Sankar
17:46>> We were targeting at that point, in the beginning it was like founders, you know, CEO, CTO. It is mostly that. And then as we sort of continue to grow and scale and expand, you know, we went into the HR job title, the IT admins and so on.
Nathan Latka
18:04Okay, very good. Now, again, you've raised $65,000,000. I imagine you guys are actively growing the team. What's the team size today?
Team Size: Engineers and Sales Reps
Prasanna Sankar
18:11>> It's around 200 people.
Nathan Latka
18:13How many engineers do you manage?
Prasanna Sankar
18:15>> A 100 people.
Nathan Latka
18:16Wow. Okay. A 100 engineers. Now do you have quota carrying reps internally for an inside sales motion or it's all channel partners?
Prasanna Sankar
18:22>> We do have quota carrying reps.
Nathan Latka
18:24How many of those?
Prasanna Sankar
18:27>> I think maybe like 20 people today.
Nathan Latka
18:29Okay, okay, very good. Now are these, are they following the same kind of inside sales playbook as you might've seen at Zenefits as well or is it totally different?
Prasanna Sankar
18:38>> It's very similar playbook. Yeah, it's not very different.
Nathan Latka
18:43Okay. So similar playbook, by way, we define as, you know, quota target is about five times what full OTE is. You have an SDR to account executive to customer success management kind of flow. Is that accurate?
Prasanna Sankar
18:56>> Yeah.
Nathan Latka
18:57Yeah. Okay, great. And then look, obviously building a big SaaS company churn is critical. It can absolutely destroy you. So when you look at your gross revenue churn over the past twelve months, what's that coming at?
Churn and Net Revenue Retention
Prasanna Sankar
19:07>> I'm not sure actually. I don't know. We look at churn all the time. The churn is seasonally high towards the end of the year in our business. And it sort of varies, fluctuates a lot.
19:20>> Yeah, I'm not really sure like where it stands today.
Nathan Latka
19:23Do you know if when you add your expansion revenue from historical cohorts back to the churn from those cohorts, is net revenue retention greater than 100%?
Prasanna Sankar
19:32>> Yeah, yeah, it is significantly greater than 100%. When we raised our last financing round from Kleiner, it was around 300% which was something abnormal. That was mostly because we were especially selling to fast growing companies so they grow. So it was abnormally high. Now as we sort of get the larger portion of the market, it is, you know, it is less impressive, but it's still pretty impressive.
Nathan Latka
19:58Yeah. Yeah. Getting that kind of a net revenue rate, the way you do that is exactly how you just described. But to your point, as you scale, right, even a 140%, 150% net revenue retention number is world class. You know, Looker was a 130% when Frank came on the show a year before the Google acquisition. So anywhere in that range is obviously super healthy.
Prasanna Sankar
20:18>> Yeah, absolutely.
Nathan Latka
20:19Most of that upselling is coming directly from seat upsells or are you upselling based off some utility metric or a feature based upsell?
Prasanna Sankar
20:26>> Most of it has been seat upsells, which is automatic, right? Like we don't even put, we have not done historically a great job on upsell so far. Right now we're sort of investing more on that, but most of it is just like organic seat ads.
Nathan Latka
20:40Very good. Okay. And so when was the Kleiner raise, the most recent raise?
Kleiner Perkins Raise and Runway Planning
Prasanna Sankar
20:44>> It was Feb last year. So around like a year ago.
Nathan Latka
20:47Okay. And how much was it for?
Prasanna Sankar
20:50>> It was like
20:53>> 45,000,000.
Nathan Latka
20:54Okay. 45. And so how were, when you and Parker got together and whoever else is on your strategy team and said, Hey, we're going to go do a fundraise. Take, you know, let's go macro here for a second. World economy today as a SaaS company that's scaling, how many months of runway are you trying to raise for just to give yourself enough cushion?
Prasanna Sankar
21:13>> We were trying to raise for like thirty months at the time.
Nathan Latka
21:18And help me, you know, why is that? You know, in the past, you know, three years ago when was interviewing founders, it might've been sounding more like eighteen months because remember the more you raise, the more dilution it is, right? So why was thirty months kind of the target?
Prasanna Sankar
21:28>> Parker has been, you know, pretty conservative on this stuff. Like, you know, you can, you know, if you can either get diluted a bit more or, you know, can run out of money. So, you know, we've always chosen
Nathan Latka
21:40Or drive you towards profitability.
Prasanna Sankar
21:44>> You can, you definitely can. You know, every round that we raise, we sort of like have the goal that, you know, that round gets us to profitability. And then, you know, there is a plan A that the opportunity in front is just like huge and you press the accelerator button where the return on investment is clearly visible and then you raise up, raise again.
Nathan Latka
22:04Yep. So just to be clear, when you raise the 45,000,000 trying to cover thirty months of burn, what I hear when you say that is you guys are totally comfortable when you look at the market and how big is you're going after burning up to $1,500,000 per month for the next thirty months.
Prasanna Sankar
22:17>> Yeah.
Nathan Latka
22:18Yeah. Very good. Alright. Anything else I missed that you definitely wanna sneak in before we wrap up?
Prasanna Sankar
22:23>> No. Great. Thanks for chatting.
Famous Five Rapid-Fire Questions
Nathan Latka
22:26Alright. Let's wrap up here with some easy ones. Famous Five. Number one, favorite business book?
Prasanna Sankar
22:31>> Hard Thing About Hard Things.
Nathan Latka
22:33Number two, is there a CEO you're following or studying?
Prasanna Sankar
22:37>> Parker.
Nathan Latka
22:39Yeah, number three. What's your favorite online tool for building the company?
Prasanna Sankar
22:45>> Asana.
Nathan Latka
22:46Number four, how many hours of sleep do you get every night?
Prasanna Sankar
22:50>> Eight.
Nathan Latka
22:51Okay. And what's your situation? Married, single, kiddos?
Prasanna Sankar
22:55>> Single kid.
Nathan Latka
22:56Okay. Good. Single with one kid. And how old are you?
Prasanna Sankar
23:00>> I'm 32.
Nathan Latka
23:02Okay. Last question. What do you wish your 20 year old self knew?
Prasanna Sankar
23:09>> That I enjoy finance as well.
Nathan Latka
23:13You enjoy wait, we didn't touch on that at all in the interview. Why do you enjoy finance?
Prasanna Sankar
23:19>> I think, you know, the two things I really enjoy are like coding and trading. Both of them require no, you know, you could be the expert, you know, like experts don't really exist. You know, they operate on very simple rules, buy low, sell high, or, you know, write some add, subtract, go to. And, you know, experts don't really matter. You can reason from first principles.
Nathan Latka
23:47Guys, you have it. Prasanna and Parker left Zenefits about the same time back in 2015, 2016. They then jumped into the new company Rippling together, raised $10,000,000 right away. Parker put in about $500,000. They split equity 60% to Parker, 40% to Prasanna. They're now scaling nicely, trying to be the all in one HR and IT tech platform currently serving 2,000 customers. Prasanna says $36,000,000 in terms of run rate is not too distant in the future. We'll
24:12see how that pans out, but they're again scaling through all kinds of channels, whether it's resellers or their 20 account executives. They've got a team today of about 200 people, 100 of which are engineers, 65,000,000 total raised net revenue retention of over 300, percent, spending about $10,000 to get a new customer for, call it, a seven to fourteen month payback period. Prasanna, thank you for taking us to the top.
Prasanna Sankar
24:33>> Thank you so much, Nathan.
Nathan Latka
24:36Do you guys know I fight like heck to get these data points for you from these CEOs that rarely do these kinds of shows? If you want more shows like this, make sure you subscribe right now. We're trying to get 10,000 YouTube subscribers by the end of September here 2019, and it would mean the world to me if you clicked now to subscribe. Additionally, I've got two more great interviews for you. If you want more data
24:59points from the world's leading SaaS CEOs, click and watch one of them right now.