Matt MacInnis

Chief Product Officer at Rippling

Matt MacInnis is CPO and former longtime COO at Rippling, a $16B+ company, known for his brutally honest leadership philosophy and building complex, high-growth businesses.

The Craftsperson The Visionary

Dimension Profile

Strategic Vision 75%

Execution & Craft 95%

Data & Experimentation 50%

Growth & Distribution 50%

Team & Leadership 85%

User Empathy & Research 40%

Key Themes

deliberate understaffing philosophy extraordinary effort for extraordinary results radical feedback culture founder intensity preservation escalation as leadership tool operational excellence

Episode Summary

Matt MacInnis shares his intense leadership philosophy from building Rippling into a $16B company, arguing that deliberate understaffing prevents politics, radical feedback is a moral obligation, and every management layer risks diluting founder intensity. His approach demands extraordinary effort for extraordinary results and treats comfort zones as danger signals.

Leadership Principles

→ Deliberately understaff every project — overstaffing creates politics, waste, and cruft
→ If you're in the comfort zone at work, you're making a mistake — 99th percentile outcomes require extraordinary effort
→ Withholding feedback is the most selfish thing you can do — it optimizes for your comfort over their growth

Notable Quotes

"It is really important to me that we've deliberately understaffed every project at the company. If you overstaff, you get politics."
— On his contrarian approach to team sizing

"The most selfish thing you can do is withhold feedback from someone. You're optimizing for your own comfort."
— On why radical candor is a moral obligation for leaders

"The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next circle of management can be an order of magnitude drop off in intensity."
— On the biggest danger in scaling companies

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