Ep. 538 - FAN FAVORITE | ClickFunnels Former COO Ryan Montgomery - How to Build an Unstoppable Distributed Team
Second in Command: The Chief Behind the Chief with Cameron Herold
Second in Command with Cameron Herold
4.9 • 224 Ratings
🗓️ 23 December 2025
⏱️ 48 minutes
🧾️ Download transcript
Summary
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
- Remote (book, Jason Fried & David Heinemeier Hansson)
- Rework (book, Jason Fried & David Heinemeier Hansson)
- Play Bigger (book)
- Silos, Politics and Turf Wars (book, Patrick Lencioni)
- The Advantage (book, Patrick Lencioni)
- V2MOM (Salesforce/Mark Benioff framework)
- Harvard Business Review – The Misunderstood Role of the COO
- Operation Underground Railroad
- Russell Brunson
- Todd Dickerson
- Tony Robbins
- Dean Graziosi
- Genius Network
- Infusionsoft by Keap
- Shopify
- Salesforce
- Amazon
Important Links
- Connect with Cameron: Website | LinkedIn
- Explore the COO Alliance - The World’s Leading Community for Seconds in Command
- Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
- Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
- 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. |
| 0:01.9 | 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. If you approach it from a remote first, if you will, or distributed first approach, I think about like, well, how are we going to build culture with a completely |
| 0:25.0 | right? If you approach it from a remote first, if you will, or distributed first approach, |
| 0:21.9 | I think about like, well, how are we going to build culture with a completely remote team? |
| 0:26.2 | It'll work even if you are in an office. |
| 0:28.4 | Right, exactly, for sure. |
| 0:29.4 | It'll work if, you know, if you have processes and tools and training and you have those things in place, |
| 0:35.3 | assuming everybody's distributed, It'll work if you get |
| 0:38.9 | together. It'll work when you go back home. It'll work when somebody's traveling. It'll work when |
| 0:42.2 | you bring on a new employee who's in a different time zone. Oh, I love that. |
| 0:44.8 | Definitely go out of your way to prepare for that. |
| 0:53.2 | Welcome to the Second and Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold. |
| 1:01.7 | 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. |
| 1:13.9 | And now, here's your host, Cameron Herald. |
| 1:22.7 | Ryan Montgomery is a leader, problem solver, and mentor. He has a background in software engineering. |
| 1:28.9 | It likes to tackle problems head-on to find solutions that work the first time. He measures his success by the success of the people around him and he strives to help his teams and peers realize their full |
| 1:33.8 | potential. When he's not working hard to be the brains behind the operation, he spends his time |
| 1:38.6 | being active and relaxing for his family, and Ryan is the C-O-O for ClickFunnels. |
| 1:49.3 | Ryan, welcome to the Second McMahon podcast. |
| 1:51.2 | Thank you for having you. |
| 1:54.6 | Yeah, I'm super excited to actually get the rest of the story here. |
| 1:57.3 | I met Russell for the first time about five years ago. |
... |
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