Sep 27, 2024 · 38m · saastr
The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale with Rippling CRO Matt Plank
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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 SaaStr session, Rippling CRO Matt Plank details the go-to-market playbooks behind scaling to hundreds of millions in ARR, highlighting human-driven outbound prospecting, specialized Product AE architectures for multi-product compound platforms, and the transition from traditional customer success to quota-carrying account managers.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 4.6 Guest teaching 5.7 Guest disagreement 1.7 Jason pushing back 1.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:23 Calling out the 'outbound is dead' consensus
Plank directly dismisses the common market narrative that outbound is dead or that AI replaces SDRs, stating that people who claim this simply do not understand outbound at scale.
Hardest push from Jason ▶ 6:05 Devil's advocate on AI replacing junior SDRsBlond pushes back on the rationale for hiring a 150-person SDR team, arguing that modern AI and account scoring could theoretically perform targeted outreach more effectively than twenty-two-year-old reps.
Biggest teaching moment ▶ 25:04 The unit economics and mini-CRO architecturePlank breaks down why launching standalone sales pods requires specific PEPM thresholds to fund dedicated leadership and create internal demand generation across core reps and AMs.
Jason holds their own ▶ 16:29 Hustle and physical door-knocking in SaaS salesBlond demonstrates his deep GTM experience by recounting how a TalkDesk SDR bypassed gatekeepers at Brex disguised as a courier, reinforcing the premium placed on high-friction sales tactics.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Scaling Outbound: Transitioning from Programmatic Outreach to SDRs | 4 | 5 | 1 | 2 | Sam Blond prompts Matt Plank on the evolution of Rippling's outbound motion and summarizes the programmatic-to-SDR shift before playing devil's advocate on AI and account scoring. Plank details how database constraints forced Rippling to build a 150-person SDR team. | |
| The Human Advantage in Outbound: Multi-Channel Prospecting and AI Limits | 3 | 7 | 3 | 1 | Plank dispels the 'outbound is dead' narrative by revealing that 50% of Rippling's outbound demos are booked over the phone. He delivers an in-depth breakdown of heuristic/ML account fit, multi-threading, intent signals, and the failure modes of generative AI email copy. | |
| Outbound Playbook Summary: Hustle, Innovation, and Sales-Marketing Alignment | 6 | 3 | 1 | 1 | Blond and Plank summarize outbound takeaways, highlighting counter-trend tactics like cold calling and tight marketing alignment. Blond shares his own anecdote from Brex about a delivery-person door-knocking tactic to illustrate raw sales hustle. | |
| The Compound Startup Challenge: Structuring Sales for Multi-Product Lines | 5 | 6 | 2 | 1 | Blond introduces the compound startup framework and asks how Rippling structured sales across 30 SKUs. Plank explains rep cognitive overload and the creation of the Product AE overlay layer when competing against point solutions like Brex and Deel. | |
| Framework and Economics for Dedicating Sales Teams to New SKUs | 5 | 7 | 1 | 1 | Plank presents Rippling's three-part evaluation framework for spinning up dedicated sales teams for new SKUs: distinct buyer persona, PEPM unit economics to support mini-CRO leadership, and phase-two purchase viability. Blond synthesizes the three criteria cleanly. | |
| Transforming Customer Success: Moving from CSMs to Account Managers | 4 | 7 | 2 | 1 | Plank walks through the transition from CSMs to quota-carrying Account Managers and explains the error of leaving retention un-incentivized. Blond and Plank clarify the fundamental difference between empathy-driven CSMs and commercial AMs. | |
| Aligning Retention Incentives and Selecting the Ideal Account Manager Profile | 5 | 5 | 2 | 0 | Blond summarizes the Charlie Munger incentive takeaway regarding retention and revenue quotas. Plank firmly asserts that he would hire an Account Manager and teach empathy 100 times out of 100 rather than trying to force CSMs into carrying a quota. |
Statements from this episode (15)
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 …”
Outbound sales drives the majority of Rippling's revenue attribution
“We're going to focus more specifically on outbound, which makes up the majority of Rippling's revenue from an attribution standpoint.”
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.”
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 …”
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: 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: 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'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…”
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: 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…”
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 …”
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.”
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…”
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 …”