Home / Lenny's Podcast: Product | Career | Growth / 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth

Dec 28, 2025

1h 36m

Explicit

Description

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you’ve ...

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

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