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.

clear all ✕

why aren't all 12 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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

Assertion Not checkable as stated
Plank: Non-US HR software markets lag the US by a decade
“All of the U S non U S markets, like starting with Canada and for sure in Europe and, you know, an APAC, like their HR software landscape is at least a decade behind where the U S is”
Matt Plank Dec 20, 2024 ▶ 51:12 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Plank: Rippling will not fund inefficient top-of-funnel spend for growth
“No matter how much money we have, we could be sitting on a billion dollars of cash. Like we are not going to go invest in top of funnel that is inefficient just to grow faster.”
Matt Plank Dec 20, 2024 ▶ 53:03 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Top sales rep win rates max out at 30% to 40%
“Even the best sales reps I know, depending on whatever segment you're in, you know, their win rates are anywhere from 15, 20%, maybe 30, 40% of the absolute highest end.”
Matt Plank Dec 20, 2024 ▶ 2:40 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
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.”
Matt Plank Dec 20, 2024 ▶ 3:21 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
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%.”
Matt Plank Dec 20, 2024 ▶ 17:22 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
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.”
Matt Plank Dec 20, 2024 ▶ 19:19 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
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.”
Matt Plank Dec 20, 2024 ▶ 48:15 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Supported
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.”
Matt Plank Dec 20, 2024 ▶ 1:07:15 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Rippling replaces existing software in almost every new customer win
“At least in our case, You know, we are ripping and replacing something pretty much every time, you know, we bring on a new customer.”
Matt Plank Dec 20, 2024 ▶ 3:33 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Rippling manages sales planning across 50 distinct sub-segments
“For us at Ripley, we have 50 different Sub-segments, right? So you have, you know, SMB, and mid-market, and enterprise, and channel sales, and product sales, and all the different products, and so, if you think about, there's like, 50, you know capacity plans …”
Matt Plank Dec 20, 2024 ▶ 13:13 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Rippling wins 50% to 60% of low-end SMB sales opportunities
“We sell the companies as small as, you know, three, four employee founders running payroll for the first time. Right. And so on the very low end of that market, you know, we win 50, 60% of the opportunities. And honestly, the majority of the ones we don't win,…”
Matt Plank Dec 20, 2024 ▶ 15:58 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Rippling's average sales cycle for mid-market deals is 50 to 60 days
“In our mid market segment where we have a 45,000 dollar average deal size, it's probably the average sales cycle is probably like 50 days. Like you'll get deals that come in and, you know, a month at the right time of year. And then you'll get deals that take …”
Matt Plank Dec 20, 2024 ▶ 19:43 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
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