Rippling GM on Running a $16B+ Company Like a Product at Scale
In this episode, Carlos Gonzalez de Villaumbrosia, CEO & Founder at Product School, interviews Anique Drumright, General Manager and VP of Product at Rippling, the workforce management platform valued at $16.8 billion with over $570 million in ARR.Anique is a product veteran who has shaped high-growth teams at Uber, TripActions, and Loom. Now at Rippling, she helps lead a workforce of over 4,000 employees, including 100 former founders, to maintain the speed and ownership typically lost at scale. In this conversation, Anique breaks down how Rippling successfully operates as a compound startup and why product leaders must evolve into General Managers.
What you’ll learn:
- How to pivot from managing a backlog to owning a P&L as a GM.
- The Compound Startup framework for consolidating enterprise categories.
- How to build high-performing teams by hiring for founder-level curiosity.
- Strategies for proving ROI to enterprise customers to drive platform adoption.
Key takeaways👇:
- Go and See: Why leaders must personally investigate customer issues to set the bar for quality.
- Singular Obsession: How to organize teams to maintain focus and velocity as you scale.
- Automating ROI: How Rippling uses product efficiency to justify headcount reduction for clients.
00:00 🚀 Building High-Performing Product Teams
00:59 🎙️ Introduction: Rippling’s Hypergrowth & Founder Culture
04:30 🦄 From Uber to Rippling: The DNA of Success
07:07 🤝 How to Earn Trust with Founder-CEOs
09:46 🔍 The Go and See Leadership Mentality
13:00 💼 The Shift from VP of Product to General Manager
16:30 🏗️ Compound Startups: Why Platforms Win
22:17 📈 Selling Efficiency & ROI to Enterprise
24:30 🎯 Strategic Planning: Big Bets vs. Incremental Wins
28:10 🗓️ Weekly Rituals for Product Executives
31:56 🔥 The Reality of High-Ownership Culture
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ABOUT US:
Product School ( https://prdct.school/3IHRjtN) is the leader in AI training for Product teams, trusted by Fortune 500 companies and a community of 2M+ professionals. Our expert-led, live, hands-on programs, run by AI-first product leaders, embed practical AI skills to help organizations innovate faster, experiment at scale, and achieve measurable business outcomes. Receive SMS online on sms24.me
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