The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 113 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 7 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Rabois: Not raising my valuation offer for Rippling was my biggest mistake
“You know, we talked about the biggest mistake ever was not raising the valuation on rippling.”
MITIMCo approved a Rippling co-investment within hours on a Friday night
“Within a few hours, Friday night we made the decision to back that deal.”
Rabois: Lost Rippling seed to Gary Tan over $10M valuation gap
“Rickling came in, Parker came in and we gave a term sheet. It was, you know, obviously controversial at the time, for the seed, and Gary Tan, initialized, also gave a term sheet. And at the time, there was about a ten million dollar gap. I probably offered fiv…”
Lewis: Rippling reached nine-figure ARR with nearly 3x annual growth
“Now they're already at, you know, nine figures of air are growing extremely fast. They grew almost three acts over the past. 1212 months.”
Geoff Lewis: Bedrock deployed 20% of first three funds into Rippling
“It's around 20% of those first three funds now. All in is rippling across all of our investments.”
Conrad: Rippling generates millions in net new ARR monthly from cross-sells
“I mean, we have sort of millions of dollars in net new ARR every month from cross sell, which is selling, You know, existing customers on new SKUs within Rippling.”
Conrad expects Rippling to be a public company by 2027
“Five years from now? I would I would hope so. I don't, you know, and to like, just to be clear for you know, there's like no plans on any, you know, people are going to be like suddenly like timing our IPO and that's not there. It's not something that we spent…”
Parker Conrad: Rippling spends over 60% of revenue on R&D
“The average B to B software company between sort of a hundred to two hundred million in ARR spends about 20% Of their revenue on R and D. We spend now, I think north of 60, 60%.”
Conrad: Rippling offers employees secondary share sales whenever founders sell
“I sold some stock, not, not in our most recent round. So I didn't sell anything in the most recent round. But I sold some stock earlier on before that, before the most recent round. And when I've done so, it's always been whenever I've sold stock as a founder,…”
Ryan Petersen: I was the first angel investor in Rippling
“I was the first investor in Rippling. Put a big check into that. Did really well.”
Altman: Hydrazine Capital backed Rippling at a $25 million valuation
“It was give money to the best people. You know, we did Reddit at a higher valuation. We did rippling at 25.”
Altman: Saga sold Rippling shares early to return capital to LPs
“Rippling and Reddit. We sold a little bit of rippling on the way up, just because, like, our LPs wanted money and, you know.”
Randle: Mamoun Hamid's top wins combine B2B software with consumer engagement
“If you think about his huge, huge winners, whether it's Figma, Glean, Rippling, they all have like a common through line of the, you know, it's B to B software, but it's almost like consumer like software that, that demands really high user love and engagement…”
Moore: Rippling expands its addressable market quarterly via product layering
“Rippling is, of course, the company that everybody loves to talk about in this sense. But I think what you see with Rippling is, like, sure, you were kind of starting up thinking about it as a payroll product, but they have just been so unbelievably effective …”
O'Driscoll: Enterprise customers must replace payroll providers facing criminal liability
“If you're relying on them to manage your payroll, to move money on your behalf, you possibly can provide them having some kind of civil liability. But if it trends over into criminal liability, you probably have to find a new payroll provider, right?”
Rippling mandates three days a week in-office for staff
“If you're in an office, for us, anywhere in the country, like, you have to be in the office three days a week.”
Plank: Rippling's average mid-market deal size is $45,000
“Our average pep-em is like 60, 70 dollars pep-em across the customer base. So for our mid-market segment, selling to companies 50 to 250 employees, the average deal size is like 45 K.”
Rippling goals its marketing team on pipeline generated, not activity metrics
“Our marketing team has a pipeline plan that they sign up for. They don't have like a, you know, how many, you know, webinars did you do and how many content downloads did you get? Like those things are important, but like their goals are how much pipeline do y…”
Plank: Prospect indecision is the primary cause of lost sales at Rippling
“You know, the number one reason why you lose a deal in most cases, at least at rippling, is indecision.”
Rippling schedules 1,000 outbound demos monthly, half over the phone
“50% of our outbound demos we book over the phone. So we schedule like a thousand outbound demos a month in our SDR org, and literally half of them are booked over the phone.”
Plank: Responding to lost sales deals with kindness yields unexpected win-backs
“If you leave every single interaction with that type of, like, mindset, I promise you, you'll get stuff that bounces back that you, like, never, like, expected to bounce back.”
Plank: Upmarket is Rippling's fastest-growing segment, competing with Workday
“The fastest growing segment, for sure, is like our upmarket segment, like our, you know, we're moving that market, like very quickly and, you know, used to not compete with the workdays of the world. And now that's weren't a lot of deals with them.”
Plank: Sales leaders get zero credit for personal execution ability
“He's like, you don't get any credit for knowing how to do something yourself. Like zero credit that you know how to do X, Y, and Z. Like your job as a sales leader is to get everybody else to do that.”
Plank: The main cause of legal deal delays is failing to parallel-track
“You have to parallel track those like legal things, budget review. You can't just like get a yes and then start all those processes over. And that's the number one reason why people push a deal, a committed deal because of legal review is like, they just didn'…”
Plank: Rippling locks in original pricing for early customers permanently
“And we don't do this by the way on existing customers. Like as we inch price up over time, like our existing customers that bought early on, like we locked them in pretty much forever.”
Plank: Rippling's mid-market win rate is 20% and enterprise is 15%
“Mid market is probably around, you know, like 20 ish percents. And then I think enterprise is maybe closer to like 15%.”
Sustaining high revenue growth requires individual business segments growing 200-300%
“If you're going to grow, you know, 6070, 80, 90% year over year at hundreds of millions of dollars, like you have to be able to have some things that are growing, you know, two, 300%. Like it's the only way you'll maintain the growth rate.”
Hamid shares entry valuations for Slack, Figma, and Rippling
“Probably Slack, I would say, you know, even at the 250 post that's, you know, with all the dilution over time and, If you take the twenty-seven billion or some other number that's a, obviously, a good, great multiple. Figma, you know, the initial investment wa…”
Grady: Kleiner Perkins partner Mamoon Hamid is an exceptional deal picker
“Somebody who I really admire is Mamoon at Kleiner. I think Mamoon has an exceptional track record of investing in companies that are not at all obvious at the time. And I think about the series B in Figma, which is a round that we looked at and passed on. I th…”
Janie Lee: Parker Conrad Is One of the Best Product Visionaries
“Parker was one of the best product visionaries I've ever had the privilege of working with. He understood the customer like no one could.”
Rippling now hires experienced SDRs due to post-layoff talent availability
“It has changed quite a bit that now we hire more people that are coming from the SDR role because there's more talent out there that's available.”
In-person events are highly effective for selling to HR leaders
“HR people love, love going to events, and so we've had a lot of success at the last couple SHRM events we've been to.”
Rippling sets fully ramped SDR quota at eight S2 opportunities monthly
“A full month's quota, if they're fully ramped is eight S twos a month. So on month one, it's like two, and then the next month is four, the next month is six, and then they're on eight.”
Rippling employs over 200 outbound SDRs
“Outbound is definitely still a thing. I have over 200 of them that would definitely prove otherwise or prove what I'm saying accurate”
Bad SDR hires are identified by month two via input KPIs
“Month two. And it's not even usually based off of the S two performance. It's usually based off of their ability to master the KPIs that come before that. So how many calls are they making a day? How many emails? We expect a certain amount of accounts and cont…”
Rippling uses fast-start spiffs requiring 50% quota in week one
“We've done a lot of spiffs that are what I'll call a fast start. And so we'll Want people to get, you know, halfway to their quota by week one of the month. And so then they're like already pacing and set up for the rest of the month.”
Rippling offers lateral career transitions outside sales for high-performing SDRs
“Our promotion path is not just to AE. There's different routes where people can go across the business because My commitment to them is, you know, if you're a good contributor to the team, you're positive, at least performing the best that you can, like we wil…”
Proactive SDRs who reach out to VPs early become top performers
“And the ones that immediately put time on my calendar, I swear are the ones that end up being successful. And it's not because of anything I did like at all, it has to do with like their proactiveness and the fact that they actually give a shit about their car…”
Neil Mehta Completed Rippling Funding Deal Over Weekend During SVB Collapse
“With Neil, for instance, I think there was a big article maybe last year about the deal he did in Rippling, right? And that came together over a weekend, right? During this bank collapse.”
Sarah Guo Regrets Passing on Benchling and Rippling at Series A
“One of the investments I, like, actually, multiple investments I regret not making, so Benchling, Rippling at the A, right?”
Lewis: Rippling customers need no payroll admins under 1,000 employees
“Rippling customers don't need to hire dedicated payroll administrators until they're over a thousand employees.”
Geoff Lewis: Bedrock heavily concentrated capital in Rippling, Vercel, and Flock Safety
“So we've concentrated capital in Rippling, Vercel, and Flock Safety to an extreme degree.”
Conrad: Rippling targets 70-80% software margins, except for lower-margin payroll
“We, I mean, so most, we really target you know, we try and maintain sort of 70 to 80% software margins for all of our products. I think the biggest exception to that for us is actually payroll where you know, payroll is much lower margin for us”
Conrad: Rippling launching Finance Cloud product covering cards and expenses
“We're very close to launching. And I think by the time this comes out, we'll already have launched our spend management what we call our finance cloud vertical, which is corporate cards, expense reimbursements, bill pay.”
Conrad: Offboarding inventory prompt adds $300k monthly ARR for Rippling
“That one ad unit, You know, adds, you know, 300 K a month in net new ARR for that SKU every single month, like clockwork.”
Conrad says he desperately never wants to start another startup again
“Starting a company is it's a real grind for a long time. Like I desperately want to never do it again.”
Conrad: Compound startups gain sales advantages by targeting multiple buyer personas
“One big advantage it gives you tactically from a sales and marketing perspective is when you have more products and more buyers, you actually have more people you can reach out to. And so if you happen to ping, in our case, the HR person, and they don't respon…”