How Rippling Built a Revenue Machine From Zero to Billions
In a packed session at SaaStr Annual, Rippling CRO Matt Plank sat down with Sam Blond (former Brex CRO, now founder and also board director at Rippling) to break down exactly how Rippling scaled from zero to a $14B+ valuation and hundreds of millions in ARR.
Contrary to the popular narrative that “outbound is dead” and “AI will replace sales,” Rippling has built a revenue juggernaut with a decidedly human-centric approach. Matt shared the three core growth tactics that transformed Rippling from cold calls in Parker Conrad’s basement to 1,500+ revenue professionals driving massive scale.
And see everyone for 200+ more sessions, workshops, 1-on-1s and more like this at 2025 SaaStrAnnual.com! May 13-15 in SF Bay!!
Growth Tactic #1: Double Down on High-Touch Outbound (Even When It Seems Counterintuitive)
When everyone zigged toward automation, Rippling zagged toward humans.
“We’re booking 1,300 outbound demos this month alone, and 50% of them are still happening over the phone,” Matt revealed.
Rippling’s outbound journey evolved significantly:
Phase 1: Programmatic Outbound (The Early Days)
- Marketing-led automated outreach
- Low-cost way to build the initial database
- 0.5-1% conversion rates
- Hit a ceiling due to database size limitations
Phase 2: Human-Led Outbound at Scale (Last 18 Months)
- Built a 150-person outbound SDR organization (from zero)
- Invested in managers, directors, VPs to support the team
- 3-7% conversion rates on the same accounts
- Now generates 50%+ of revenue with plans to reach 60%
The counterintuitive insight: While competitors rushed to automate everything with AI, Rippling found that human persistence, creativity, and good old-fashioned cold calling created a competitive advantage.
“Cold calling is almost a lost art. Many companies don’t do it anymore, which actually makes it more effective today,” Matt explained.
Rippling does use AI for account scoring and targeting, but maintains that human SDRs bring three irreplaceable elements:
- Personalization that AI often gets wrong
- Multi-channel saturation (especially phone)
- Creative hustle that differentiates in a crowded market
Matt’s advice: “The more effort something takes, the higher the yield. Email is easy. Cold calling is harder. Showing up at someone’s office? That’s compound hustle that drives results.”
Growth Tactic #2: The Compound Startup Approach to Product Expansion
Rippling has expanded from 4 products to 30+ in just a few years, exemplifying what Parker Conrad calls the “compound startup” approach – continuously launching new products to drive expansion.
But with each new product, the go-to-market motion became increasingly complex. When Rippling reached about 15 products, Matt realized their sales reps couldn’t effectively absorb information about all products, especially when competing against specialized point solutions.
The breakthrough solution:
Three-Team Structure:
- Core New Logo Representatives – Focus on landing the initial deal
- Account Management Teams – Own customer relationships and retention
- Product Account Executives – Product specialists who co-sell with both teams
When to give a new product a dedicated sales team comes down to three key criteria:
- Different buyer persona from core product
- Unit economics support building a dedicated team
- Phase 2 purchase pattern vs. being evaluated alongside core products
“For a new product launch, we essentially create a mini-CRO structure – a dedicated leader who owns that product’s growth and works closely with product, marketing, and sales teams,” Matt explained.
This approach has allowed Rippling to simultaneously compete in multiple markets with specialized sales teams while maintaining coordination across the business.
Growth Tactic #3: Reimagining Customer Success for Retention AND Growth
Rippling’s approach to customer success evolved dramatically as they scaled.
Initially, they had CSMs as the only post-sales resource. As they grew, they tried having CSMs own cross-sell opportunities, but this proved ineffective.
The winning formula came from a complete restructuring:
- Sales-oriented account managers replaced traditional CSMs
- Dual quota responsibility – both revenue AND retention metrics
- Tag-team approach – Account managers own relationships but bring in product AEs for specialized selling
“The moment we tied compensation to retention, behavior changed dramatically,” Matt explained. “But simply adding retention metrics wasn’t enough. We also had to give them the capacity to actually focus on retention by bringing in product AEs for complex selling.”
The most surprising insight: Matt believes it’s easier to teach revenue-generating salespeople to have empathy than to teach customer success managers to generate revenue.
“It’s a cultural thing that humans can learn. Start with a quota-carrying, revenue-generating team and teach them empathy, rather than trying to transform CSMs into a revenue team.”
The results speak for themselves – Rippling has “massively beaten” their baseline churn numbers every month since implementing this structure.
Key Takeaways for B2B Leaders
- Outbound isn’t dead – it’s evolving. Human outbound actually produces better results when everyone else automates.
- The compound startup approach requires specialized sales teams – don’t expect generalist reps to compete with specialists.
- Customer success structure matters more than you think – tie compensation to both retention and growth, but give your team the capacity to focus on both.
Rippling’s journey from zero to billions shows that sometimes the most effective growth tactics run counter to conventional wisdom. When everyone else is automating, personalizing can be your edge.
- SEO Powered Content & PR Distribution. Get Amplified Today.
- PlatoData.Network Vertical Generative Ai. Empower Yourself. Access Here.
- PlatoAiStream. Web3 Intelligence. Knowledge Amplified. Access Here.
- PlatoESG. Carbon, CleanTech, Energy, Environment, Solar, Waste Management. Access Here.
- PlatoHealth. Biotech and Clinical Trials Intelligence. Access Here.
- Source: https://www.saastr.com/the-revenue-playbook-ripplings-top-3-growth-tactics-at-scale-with-rippling-cro-matt-plank/
