Matt Plank
Chief Revenue Officer, Rippling. On 2 shows, 3 appearances. The Shows tab opens the full record on each.
executiveoperatorrippling.com ↗
Joining as employee #5 and the first sales hire at Rippling, he built the company’s outbound engine and scaled global revenue operations. Prior to Rippling, he managed enterprise sales teams as a Sales Director at Zenefits and worked in sales at EchoSign.
2shows
3appearances
63statements
1resolved
1supported
0contradicted
100%fully supported
10said about them ↓ Everything Matt Plank said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Plank: People calling outbound sales dead lack experience or seek clout
“I think people that say outbound is dead are either one of two things. Like they're either engagement bathing, you know, looking for a reaction on LinkedIn or whatever that they know that there's a whole army of people out there where that's their profession a…”
At $200M revenue, CRO role shifts from closing deals to sales operations
“By the time you get to be maybe, I don't know, two hundred million or something, like your job as the CRO, it completely changes to essentially like head of sales operations. Like you have a great sales operations team, but
At some point it transitions complet…”
Plank: Customer success managers cannot be turned into quota-carrying sales reps
“A sales DNA at the core is just, you can get those people to have like empathy for the customer and like understand and care about making them successful, but I don't think you can take a CSM and make them, you know, like a quota carrying rep.”
Plank: A 60-70% sales win rate indicates underpricing or narrow targeting
“You don't want win rates that are 60, 70%. You're either not in enough deals, right? Like you're just way too narrow or your price is way too low. Like, if you win 70% of deals, then, like, that's not good. That's a bad, or at least you could go much bigger, r…”
Plank: Rippling account executives have zero outbound prospecting targets
“Outbound SDRs own the quota. Like they schedule the demos. If you're a rep at Ripley and you have zero, like actual prospecting targets.”
Plank: Rippling couldn't compete in niche verticals without specialized reps
“Had we not done that, We never would have been able to compete in these kind of, like, hyper-competitive, like, vertical spaces like finance and global payroll”
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: Founders wait too long to hire GTM leadership
“Founders definitely should not create the playbook, but I think founders wait too long to hire a go-to-market, and I think they do that because they feel like they can't hire a good salesperson potentially without a bunch of traction.”
Rippling ties account manager compensation 70% to new business, 30% to retention
“I think, like, 70% of it is tied to selling new business, and 30% roughly is tied to retention, specifically, like, dollar retention, and it completely changed everything in our, you know, like, have just, like, out, completely outlier, like, off the charts, l…”
Plank: Discounting is a made-up concept and list prices do not matter
“Discounting is a completely like made up thing. Like at the end of the day, what the only thing that matters is like net price, right? And so discounting is simply a factor of like, where do you set your list price? Like list price doesn't matter, right? Like …”
Plank: Early startups should never turn down any non-zero price deal
“I think the first one is when you're a, you know, zero to one company, whatever, you're a million bucks, two million bucks, like early, early stage, like nothing matters. The only thing that matters is winning customers. It doesn't matter what they pay. It doe…”
Plank: Time-based discounts without trust are counterproductive in enterprise sales
“People do not sign contracts on the last day of the month because they're worried that their discount's gonna go away. Like, that's absolute bullshit. Like, if you ever bought software and it's the 31st of the month, and someone's like, you have this quarter-e…”
Plank: Sales deals delayed by stakeholder or budget changes start over
“There's no such thing as like delaying a deal for like those types of reasons. Like you're starting over from scratch. You might not know it, but you're starting over from scratch.”
Efficiency does not matter for early startups, but becomes the top constraint
“When you're in an early stage company, like efficiency, like doesn't really matter. Like you don't even have a business, right? Like it's not about how efficient are you? It's like, you're just trying to win any way possible and you're losing money and all tha…”
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”
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.”
Plank: Post-COVID drops in baseline hustle make intense effort a larger advantage
“Working your ass off and hustling is like has always been able to get you ahead, but there was a culture pre COVID where that was like table stakes and what everybody did and you were in the office all the time and you showed up at eight and left at six. And i…”
Plank: Sales leaders should work for CEOs with uncomfortably high expectations
“I think more than anything Like you really should work for a CEO who's like, whose ambition and expectations make you deeply, deeply uncomfortable. Like that, that is, I think if you think about like, you know, some huge, like, you know, sports nerd, and it's …”
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 …”
The other half of the tape: Matt Plank's own voice is left out of every number here. Other people bring the name up 9 times in 6 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Sam Blond 4Ashley Kelly 3Harry Stebbings 1Brendon Cassidy 1
Statements about Matt Plank, by other people (1)
Rippling reached a $14B valuation with hundreds of millions in ARR
“Rippling is a 14 plus billion dollar, many thousands of employees, I think 1500 folks in the revenue organization, several hundred million dollars of ARR, and Matt grew that organization and that revenue number from making cold calls in Parker's basement just …”
Every mention by year
tap a year for its mentions
20VC 5
the Official SaaStr Podcast 4
2025 1 mention in 1 episode
2024 4 mentions in 2 episodes 2 per episode
2023 4 mentions in 3 episodes 1 per episode
- CRO Confidential: Sales Recruitment and Hiring Managers With Ben Braverman
- SaaStr CRO Confidential: Principles that Drove Wiz’s $0 to The First $100m ARR | Wiz CRO Colin Jones
- SaaStr CRO Confidential:Hiring a Great VP of Sales Today Sam Blond + Former Lattice CRO Dini Mehta
- every mention in 2023, scene by scene →
One line per show, most statements first. The link opens Matt's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | Chief Revenue Officer, Rippling | 1 | 40 | 100% 1/1 | full record on 20VC → |
| SAASTRLEDGER | Chief Revenue Officer, Rippling | 2 | 23 | — | full record on the Official SaaStr Podcast → |