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Matt MacInnis

1 episode

Episodes

"I deliberately understaff every project" | Leadership lessons from Rippling's $16B journey

Dec 28, 20251h 36m

Guest: Matt MacInnis - Chief Product Officer at Rippling. Matt has been instrumental in Rippling's success, previously serving as COO, and has a reputation for brutal honesty and clear articulation of his learnings. Key Takeaways: Deliberately understaff projects to avoid politics and inefficiencies; focus on high-priority tasks. Extraordinary results require extraordinary efforts; if you're comfortable, you're likely not achieving your potential. Feedback is crucial; withholding it is selfish. Escalate issues to improve systems and processes. Product market fit is unmistakable when achieved; if uncertain, it's likely not there. Consider quitting if pivots don't yield results. In AI and SaaS, owning first-party data is crucial for leveraging AI effectively. Point solutions may struggle without this advantage. Topics Covered: Understaffing projects, extraordinary efforts, feedback and escalation, product market fit, AI in SaaS, leadership intensity, investing insights, frameworks for hiring and management.

Notable Quotes

โ€œIf you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult.โ€

Extraordinary Efforts

โ€œThe extraordinary effort thing is a reminder that it's supposed to be really fricking exhausting.โ€

Work Intensity

โ€œIt's a very special and rare thing, and it gives me a superpower as a leader because I can lean on that when I'm ringing the oil out of somebody who's in the bored and tired zone.โ€

Leadership