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.
Credits:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Anique Drumright
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