Dec 20, 2024 · 1h 10m · news
Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the 20VC podcast, host Harry Stebbings interviews Matt Plank, Chief Revenue Officer of Rippling, to dissect the operational playbooks and structural philosophies behind scaling a highly efficient, multi-million dollar enterprise sales machine.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 14.9% of the talking time here. How this is scored →
Harry as informed peer 3.0 Guest teaching 6.6 Guest disagreement 2.0 Harry pushing back 3.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:05 Calling 'outbound is dead' absurd
Matt forcefully rejects the popular narrative that outbound sales is dead, dismissing proponents of that view as engagement baiters on LinkedIn or inexperienced operators.
Hardest push from Harry ▶ 51:05 Challenging Australia expansion rationaleHarry aggressively challenges Rippling's international strategy, mockingly questioning why the company bothers expanding into small markets like Australia when US market expansion remains wide open.
Biggest teaching moment ▶ 28:28 Why 70% win rates indicate pricing failureMatt re-educates Harry and early founders who brag about 60-70% win rates, explaining that high win rates demonstrate severely underpriced software or overly narrow pipeline targeting.
Harry holds his own ▶ 44:28 Pushing back with CRO consensus on rep prospectingHarry uses consensus from previous CRO guests to challenge Matt's model, arguing that expecting dedicated outbound SDRs to feed account executives without AE self-prospecting is presumptuous.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Are Salespeople Born or Made? | 3 | 5 | 2 | 4 | Harry strongly rejects Matt's perspective on accepting loss in sales, stating he hates losing and expects extreme pain from defeat. Matt calmly reframes this dynamic, explaining that even top-tier reps lose the vast majority of opportunities due to prospect indecision and ghosting. | |
| Replacement vs. Net New Categories | 3 | 6 | 4 | 3 | Harry sets up a provocative framing that outbound sales is dead in 2024. Matt forcefully rejects the premise, calling claims that outbound is dead absurd, insane, and mere LinkedIn engagement baiting. | |
| Building an Effective Outbound Function | 2 | 7 | 1 | 2 | Harry asks how to operationalize marketing and sales tightness. Matt outlines Rippling's outbound machinery, explaining how marketing curation feeds SDR execution without finger-pointing over pipeline credit. | |
| The Art of Capacity Planning and Setting Quotas | 3 | 7 | 1 | 2 | Harry asks how top-line pipeline targets are split across deal sizes. Matt details how CRO responsibilities shift toward RevOps capacity planning across 50 distinct sub-segments. | |
| Deconstructing Close Rates and Sales Cycles by Segment | 3 | 7 | 1 | 2 | Harry drills into win rates and unit economics across SMB, Mid-Market, and Enterprise segments. Matt breaks down the funnel conversions, sales cycle lengths, and per-employee-per-month ACV metrics. | |
| CS vs. AM: Transitioning to Quota-Carrying Account Management | 5 | 6 | 2 | 4 | Harry cites Snowflake CRO Chris Dagnon's stance that Customer Success is BS to challenge Matt. Matt partially agrees for multi-product companies, explaining why Rippling transitioned to quota-carrying Account Managers. | |
| Demystifying Discounting: Net Price vs. List Price | 1 | 8 | 2 | 2 | Harry candidly admits he does not understand list price versus net price dynamics. Matt educates him on discounting policies and why list prices are arbitrary baseline numbers. | |
| Pricing Friction: Finding the Limit and Raising Prices | 3 | 8 | 2 | 3 | Harry asks when founders know pricing has hit its ceiling. Matt counters common founder pride around 70% win rates, explaining that extremely high win rates signal underpricing. | |
| The Value of Multi-Year Contracts and Kickers | 3 | 7 | 3 | 2 | Harry asks how to drive sales urgency beyond pricing discounts. Matt calls standard end-of-quarter artificial discounting absolute bullshit unless backed by real mutual trust and timeline alignment. | |
| Poking Holes: Conducting Effective Deal and Pipeline Reviews | 4 | 7 | 2 | 4 | Harry questions why legal review delays are unacceptable excuses for deal slippage when reps do not control prospect legal teams. Matt explains that skilled reps parallel track legal processing during valuation. | |
| Leading with Extreme Ownership and Morale Management | 2 | 7 | 1 | 1 | Harry asks how to manage team morale during volatile market downturns. Matt outlines extreme leadership ownership, citing Parker Conrad's advice that leaders get zero credit for personal execution. | |
| The Outbound Funnel: Sales Reps vs. SDRs | 5 | 7 | 4 | 5 | Harry challenges Matt by noting that virtually every other CRO guest insists sales reps must prospect their own leads. Matt strongly defends keeping AE calendars focused purely on closing while SDRs handle outbound. | |
| International Expansion and Efficiency Challenges | 3 | 6 | 1 | 3 | Harry inquires about underperforming growth areas, leading Matt to acknowledge international expansion hurdles due to unit economics and CAC constraints in net new geographies. | |
| Why International Expansion is Worth the Fight | 4 | 7 | 3 | 6 | Harry bluntly asks why bother expanding to small markets like Australia and why not burn capital inefficiently early on. Matt defends financial discipline and explains how legacy international HR tech is ripe for disruption. | |
| The Founder's Role in Sales and the Trajectory of Early Sales Hires | 4 | 7 | 3 | 4 | Harry cites Chad Peets' view that founders should not build playbooks. Matt agrees founders shouldn't write playbooks but pushes back on waiting for traction, advising founders to hire high-slope sales leaders early. | |
| Attracting Sales Leadership and Scaling with the Company | 4 | 7 | 1 | 3 | Harry cites Jason Lemkin regarding early VP of Sales churn and asks Matt how he personally managed to scale past $10M ARR. Matt attributes his longevity to hiring overqualified leaders and making hard calls on homegrown managers. | |
| Respecting Legacy Competitors | 2 | 5 | 2 | 3 | In quickfire, Harry asks which competitor Matt respects most. Matt names Paylocity and admits that losing to legacy payroll vendors means his sales team got out-executed. | |
| The Value of In-Person Company Culture | 2 | 6 | 2 | 2 | Harry asks for advice for new sales leaders. Matt advises ambitious executives to work for demanding CEOs whose intense expectations make them deeply uncomfortable. | |
| Splintering the Rippling Sales Organization | 2 | 6 | 1 | 1 | Harry asks about impressive recent sales strategies. Matt describes splintering the sales org into specialized product AE overlays to compete against point-solution competitors. |
Statements from this episode (40)
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.”
Plank: Scaling companies fail to raise prices until finding friction
“The big mistake that people make as they transition to the next phase is people don't increase price into a point where they find friction.”
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.”
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.”
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.”
Plank: Replacing existing software budgets is easier than creating new categories
“I think it's way easier when you're replacing something. In my opinion when you're trying to create a category or you know, create budget for a thing that doesn't exist, there's just a whole bunch of different things that you have to go through.”
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…”
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.”
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…”
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 …”
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: 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,…”
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%.”
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.”
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 …”
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.”
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: 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 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: Multi-year sales kickers should equal 10-20% of year-one commission
“You want to make sure that the kicker you're paying on a deal isn't much more than like, you know, let's call it like 10, 15% of the deal, right? So maybe if you're, if your commission rate is 20%, then maybe you're giving them an extra like two to three perce…”
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.”
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: 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: 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: Rippling had zero outbound sales generation until 2022
“Up until two years ago, Like the sales org myself and like everyone that reported to me literally never once thought about generating an outbound demo or like even like it was 100% like demos pop up on your calendar.”
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: 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.”
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.”
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: Two rapid promotions at one firm signals a top sales hire
“But when you find someone that's been promoted two times at the same company, it's like an immediate signal that that person is good, right?”
Plank: Sales leaders fail to scale when they stop leading from the front
“When someone is not scaling I think there are two things. I think one is they end up becoming like they're leading from the back and not the front. And what I mean by that is they're, they believe that their job now is to like tell people like what to do becau…”
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…”
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: 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 …”