One-on-One Meetings and the User Manual

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.