DiscoverIn DepthHow to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

Update: 2024-04-251
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Description

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple.

In today’s episode, we discuss:


  • Lessons on culture, org-design, and product from Rippling

  • Characteristics of great CEOs

  • How to a better executive leader

  • Leading with kindness and impatience

  • How to fight entropy

Referenced:

Where to find Matt MacInnis:

Where to find Brett Berson:

Where to find First Round Capital:

Timestamps:

(00:00 ) Introduction

(02:14 ) Great CEOs don’t worry about their weaknesses

(06:31 ) The third-time founder mindset

(08:09 ) Why every great CEO is impatient

(11:54 ) How executives fight entropy

(19:11 ) Experience ≠ wisdom

(21:26 ) Managing workplace politics

(24:02 ) Why all businesses should dogfood

(26:20 ) Overseeing employee expenses

(27:43 ) The best CEOs don’t need coaching

(29:55 ) The hidden cost of advice

(40:40 ) Why execs are “tortured but happy”

(44:16 ) Clear versus first principles thinking

(51:09 ) Finding first principles thinkers

(53:13 ) Why people overcomplicate culture

(55:53 ) Don’t make this mistake when interviewing

(59:26 ) The importance of anti-patterns

(61:27 ) Important business values

(63:28 ) How Matt thinks about output

(66:33 ) Rippling’s key leadership principle

(71:02 ) Why kindness matters

(72:03 ) Freeing yourself from self-doubt

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How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

First Round