Ever wondered why so many remote teams fall apart while others scale to $100M and beyond… without burning out? This episode is a raw, practical look at exactly what it takes to build and lead a remote-first organization that actually works, not just in theory, but in the trenches.

Cameron Herold sits down with Ryan Montgomery, COO of ClickFunnels, to expose the real playbook behind thriving distributed teams, rapid-fire decision making, relentless innovation, and building systems that keep a visionary CEO’s wildest ideas on track. You’ll hear the battle-tested culture moves, hiring decisions, and frameworks that eliminated chaos as ClickFunnels vaulted from scrappy startup to industry king.

Don’t let unpredictable growth, relentless tech changes, or a “too many ideas” CEO destroy your progress! Listen now for exclusive, battle-proven insights you won’t get on any other COO podcast. Miss this conversation and risk getting left behind chasing hacks instead of building something legendary.

Timestamped Highlights

[00:00 ] – How a rejected idea turned into a $100M phenomenon

[02:35 ] – The radical decision that forever changed ClickFunnels’ growth

[04:28 ] – Why most teams struggle with remote culture—and the proven fix

[09:55 ] – The secret to keeping a visionary CEO happy without burning out your team

[13:39 ] – What to throw away from your last company if you want to survive hypergrowth

[18:44 ] – How ClickFunnels keeps employee turnover shockingly low

[25:31 ] – The Go Meeting: an addiction for solving obstacles at lightning speed

[32:06 ] – When and why “killing sacred cows” saved the company

[41:03 ] – What Ryan wishes he’d known before leading thousands through explosive change

About the Guest

Ryan Montgomery is the Former Chief Operating Officer at ClickFunnels, where he’s been instrumental in scaling the company from a small startup to a global, remote-first powerhouse serving nearly 100,000 customers. A seasoned software engineer and relentless problem solver, Ryan is celebrated for building high-performance teams, architecting resilient systems, and distilling visionary energy into repeatable growth engines.

🔗 Website

Resources & Mentions

1. Remote (book, Jason Fried & David Heinemeier Hansson)
2. Rework (book, Jason Fried & David Heinemeier Hansson)
3. Play Bigger (book)
4. Silos, Politics and Turf Wars (book, Patrick Lencioni)
5. The Advantage (book, Patrick Lencioni)
6. V2MOM (Salesforce/Mark Benioff framework)
7. Harvard Business Review – The Misunderstood Role of the COO
8. Operation Underground Railroad
9. Russell Brunson
10. Todd Dickerson
11. Tony Robbins
12. Dean Graziosi
13. Genius Network
14. Infusionsoft by Keap
15. Shopify
16. Salesforce
17. Amazon

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 Cameron’s leadership 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.