Rippling GM on Running a $16B+ Company Like a Product at Scale Anique Drumright E283

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 Social Links: Find out more about Product School here Follow our Podcast on TikTok here Follow Product School on LinkedIn here

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Rippling GM on Running a $16B+ Company Like a Product at Scale Anique Drumright E283 is an episode from The Product Podcast by Product School.

This episode is 33:14 long.

This episode was published on Jan 21, 2026.

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