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 23 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 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
Plank: 50% of Rippling's outbound demos are booked over the phone
“And the reality is that's because 50% of our demos that are booked in outbound are booked over the phone.”
Plank: Cold calling is more effective today because competitors abandoned it
“I think picking up the phone and calling people is like a lost art. I think a lot of companies just don't do that anymore. And it may even be why it's more effective today is because everyone's cold calling doesn't work. We got to do other things.”
Rippling repeatedly raised early prices and removed pricing from its website
“We increased our pricing like multiple times in the early days pretty dramatically. And we, and when we did it, we actually removed it from our website as well.”
Plank: Rippling's 150 outbound SDRs achieve 3% to 7% conversion
“If you fast forward to today, 10 months later, we have about a 150 outbound SDRs. And the conversion that we get is between three to seven percent on the same accounts, right? And so if we now reach out to a thousand accounts, depending on the segment, we get …”
Rippling's generalist reps lost early deals against Brex and Ramp
“And then once we had a core rep trying to sell as the 15th SKU and compete with a new logo rep at Brexer Ramp, like we were just getting our butts kicked. Like it wasn't, we were just like, this doesn't, like we couldn't iterate fast enough. We couldn't keep u…”
Plank: Product sales teams require dedicated leadership, not just AEs
“Having a rep who's a product AE, that in itself does not get you even halfway there to what you need. You need to be able to have the reps, the managers, the director, and most importantly, you need the like mini CRO who spends every single second of their day…”
Plank: Routing add-on cross-sells back to new-logo AEs never works
“What would happen is they would, when somebody wanted to buy a new product, they would float it back to the new logo rep that closed it maybe two years ago. So a new logo rep's doing like 20 demos a month of new logos that are much, much larger deal size. And …”
Plank prefers hiring sales-oriented account managers over giving CSMs quotas
“If you have to choose between a CSM profile that's going to own revenue or an account manager profile that needs to be like customer success oriented, a hundred times out of a hundred, I'm picking the account manager that needs to be customer oriented because …”
Rippling schedules demos directly for reps rather than requiring self-sourcing
“I was always a big believer in, and really still to this day, like we put demos on reps calendars. We did not hire reps to be like, go out and, you know, kind of build your own pipeline.”
Rippling doubled revenue per customer with zero drop in win rates
“We increased pricing pretty dramatically and nothing changed. Like the wind rates didn't go down at all. You know, we just started making two, three times more per customer.”
Plank: Total addressable market is constrained by contacts, not accounts
“Your TAM is really constrained by the number of contacts, not the number of accounts. If you have a million accounts and one persona to reach out to, you have a million contacts. But if you can reach out to four, five, six, seven different people within an acc…”
Plank: Low PEPM SKUs cannot support dedicated sales teams
“If you have 15 products, where you charge five to 10 dollars PEPM for all of them, and you launch a 16th product, where you also charge 10 dollars PEPM, like you can't build the whole sales team around a single SKU, where like the unit economics, you can't set…”
Rippling moved its CSM organization into the sales org around 2022
“In fact, at the time, the CSM org reported into our VP of customer experience who owned like implementation and support. And so we actually moved it over into the sales org probably about two years ago.”
Software provisioning per new hire surged from 2-3 to 20-50 accounts
“If you think back to 10 years ago when you hired a sales rep, it was like maybe two to three accounts you would set up for them. It was like, here's your email and here's your, you know, video conference tool. And today when you hire a sales rep, there are pro…”
Plank: Expecting immediate measurable results ruins channel sales strategies
“I think one of the things that I think people make the mistake that people make or one mistake people make in channel is they expect, like they expect immediate results and they expect to be able to measure the impact of the channel, like incredibly directly. …”
Rippling built a Bangalore-based sales team to efficiently target US SMBs
“We built a sales team that we have today based out of Bangalore that today I think is like 15, 16 people, a director, a couple of managers. And those folks are like incredibly efficient from how, you know, compared to kind of how much revenue they close.”
Plank: Rippling achieved 0.5% to 1% conversion on programmatic outbound
“At the time we were getting around like a 50 bips to one percent conversion on programmatic outbound. So we would reach out to a thousand accounts and we would get basically somewhere between five to 10 demos right through the programmatic outbound.”
Rippling uses three distinct sales teams to sell complex product suites
“There's three teams that sell stuff at Rippling. There's the core new logo rep who touches every single new logo on the way in the door. There's the account management team who owns every single customer post sales. So those are like mutually exclusive. And th…”
Plank: Rippling tied AM comp to retention and massively beat churn baselines
“And we're going to actually tie comp to retention as a number. And like, just dramatically changed the behavior and the impact and results this year. Like our baseline of churn and from the account management org is like just a number that we just massively be…”
Early Rippling had no paying customers, selling exclusively to YC startups
“And so at that point we were really just selling to YC companies. Like we had come out of the recent winter batch. And so that was really what our top of funnel was selling to other YC companies in the batch. And we were really starting from zero. I mean, we h…”
Parker Conrad hustled a free Outreach seat for early Rippling
“Parker actually convinced Riley, who was, had moved over from Zenefits to Outreach to give us, like, a free seat in the early days which was a great play because we became a big customer of theirs.”
Rippling unlocked early outbound by pitching IT automation instead of HR
“And so what, the way that we kind of described what we did to people was we basically wrote an email that was something along the lines of like, look, I'm sure that you have like you know, an automated process for like onboarding employees and managing HR and …”