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Second in Command: The Chief Behind the Chief with Cameron Herold

Ep. 555 - FAN FAVORITE | Rippling COO Matt MacInnis - How to Crush Politics, Bureaucracy, and Deadly Layoffs Like a Pro

Second in Command: The Chief Behind the Chief with Cameron Herold

Second in Command with Cameron Herold

Business, Entrepreneurship, Careers, Management

4.9 • 225 Ratings

🗓️ 19 February 2026

⏱️ 47 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics?

If you’re craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.

The pain of “going it alone” is real. Tune in to learn how to avoid disaster, dodge politics, and harness proven tactics you won’t find in any business book. Don’t wait until burnout bites. Listen now for fiercely exclusive COO insights, bold truths, and systems that will let you scale smarter, not harder.


Timestamped Highlights

[00:02:22] – The hidden pain in HR, IT, and how Rippling breaks the “original sin” of bad data

[00:05:55] – Why Matt almost walked away—then got schooled by Parker’s contrarian “rocket ship” logic

[00:08:30] – The untold power of preexisting trust between CEO and COO—and what happens if you hire without it

[00:12:49] – Topgrading secrets: Why most executive hiring fails and how to get it right (even when everyone says they’re an “A player”)

[00:15:44] – Copilot dynamics: How Matt and Parker run the company with surprisingly little contact (and why it works)

[00:19:18] – Should you debate the CEO in front of the team? The cathartic, risky art of public disagreement

[00:23:13] – Inside Rippling’s flywheel advantage—what Salesforce, Facebook, and Brex did differently and why you can too

[00:31:04] – Killing bureaucracy and politics: The simple rule for hiring and process that most leaders ignore

[00:39:29] – The brutal, proven formula for layoffs: What Sequoia teaches (and how to survive the “survivor’s guilt”)



About the Guest

Matt MacInnis is the Chief Operating Officer of Rippling, a revolutionary all-in-one HR and IT platform transforming how businesses scale and manage people. Matt was also the co-founder and CEO of Inkling, a mobile learning platform that raised over $100M before its acquisition. With deep roots at Apple and a Harvard engineering degree, Matt blends big-company brilliance with entrepreneurial firepower. He’s known for breaking boring business norms and igniting hyper-growth, all while refusing to tolerate politics, inefficiency, or shallow executive hiring.

🔗 LinkedIn | Website



Mentioned Resources

  1. Inkling
  2. Apple
  3. Harvard
  4. Parker Conrad (Rippling CEO)
  5. ADP
  6. Gusto
  7. Dropbox
  8. Slack
  9. Workday
  10. Okta
  11. Brex
  12. Marketo
  13. Salesforce
  14. Sequoia
  15. Kleiner Perkins
  16. Brad Smart (Topgrading) | Topgrading (book)
  17. Who (book) | Geoff Smart (Who)
  18. Elad Gil | The High Growth Handbook



Important Links

  1. Connect with Cameron: Website | LinkedIn
  2. Explore the COO Alliance - The World’s Leading Community for Seconds in Command
  3. Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
  4. Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
  5. Chat or video call with AI Cameron via Delphi



Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.




The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Transcript

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0:00.0

Just a quick note before we dive in. This is actually one of our older episodes, but we're bringing it back because it's one of the most downloaded ones we've ever released. Clearly, it struck a chord with a lot of listeners, and I know there's so much value packed inside. So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite. One thing that's important to me as a leader is that I have to check in on the individual and how they're doing, which serves as the foundation to our relationship. Then I like to check in on us and how our relationship is going. And then on top of that, we can talk about the tasks that have to get done. You know, you can't just run into a one-on-one and say, like, hey, how's this's the project? If your one-on-one is not the space that offers an employee the opportunity to talk about

0:42.5

themselves or to talk about their relationship with you or others, you're guaranteed

0:45.9

they have no other place for it.

0:52.6

Welcome to the Second and Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold.

1:01.1

In the Second in Command podcast, we talk to top COOs who share the insights, strategies, and tactics that made them the chief behind the chief.

1:10.3

And now, here's your host, Cameron Herald.

1:16.8

Matt McGinnis is the chief operating officer at Rippling,

1:19.9

where he oversees business operations.

1:22.1

From 2009 to 2018, he was a co-founder and CEO of Inkling,

1:26.4

a mobile learning platform that provides the on-job

1:28.8

training for companies, including McDonald's and Whole Foods. Inkling was named as one of the

1:33.3

fast companies, most innovative companies, and raised over $100 million in funding before being

1:37.2

acquired in 2018. Before Inling, Matt spent eight years at Apple growing the use of products

1:42.0

and education and the sciences. He holds an electrical and computer engineering degree from Harvard.

1:46.5

So he is actually one of the smart guys because when I went to university, I couldn't spell Harvard.

1:50.6

Matt, welcome to the second in command podcast.

1:53.1

Thanks.

1:53.4

Look, the only thing that I learned by studying, I learned two things by studying engineering at Harvard.

1:58.6

One, it's like studying fine arts at MIT. It's not worth much. And number two, I learned that I wasn't a very good engineer, which is why I went into marketing. So I appreciate to bring it up the amount of money my parents spent on that to learn those two things. It's still a pretty amazing experience to be able to go there. So that's pretty cool. It was awesome.

2:21.2

Can you just give us a quick background on exactly what Rippling is?

2:24.7

Yeah, Rippling is an all-on-one HR and IT platform.

2:29.3

The way that I would look at it is basically any business, you know, up to one or two thousand employees has this massive hidden pain that they manually shuttle data from, you know, their HR system to their

...

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