Podcast Summary: Second in Command with Cameron Herold

Episode 538 - FAN FAVORITE | ClickFunnels Former COO Ryan Montgomery - How to Build an Unstoppable Distributed Team
Release Date: December 23, 2025
Guest: Ryan Montgomery, Former COO of ClickFunnels
Host: Cameron Herold

Main Theme

This fan-favorite episode features Ryan Montgomery, former COO of ClickFunnels, discussing how he helped build a high-growth, unstoppable, and distributed (remote-first) team at one of the world’s leading marketing platforms. The conversation dives into ClickFunnels’ journey from a start-up to a major player, emphasizing the intentional building of remote culture, evolving leadership, scaling pains, maintaining employee engagement, and lessons learned from rapid growth.

Key Discussion Points and Insights

1. The Origins and Scale of ClickFunnels

• ClickFunnels Beginnings: Co-founded by Russell Brunson and Todd Dickerson to simplify online selling for entrepreneurs—eliminating the need for technical know-how in marketing online.
• Growth: ClickFunnels grew from a small start-up to nearly 100,000 customers and 350+ employees, while remaining bootstrapped and declining venture capital.
  • “We sort of famously have not accepted any venture capital. Right. We've bootstrapped our whole company as much success as we've had, we've had to really earn it.” — Ryan Montgomery [08:10]

2. Distributed Team & Remote-First Culture

• Remote-First Ethos: ClickFunnels made a strategic choice to be distributed, inspired by books like “Remote” and “Rework” by the Basecamp founders.
  • Benefits: Access to the best talent regardless of location; more flexibility; asynchronous work embraced.
  • Challenges: Harder to build culture, requires intentional processes and tools.
• Tactics for Remote Success:
  • Level the playing field: “If you approach it from a remote-first... culture, it’ll work even if you are in an office.” – Ryan Montgomery [00:17]
  • Prepare for different time zones—avoid recurring meetings that exclude some team members.
  • Default to asynchronous communication (Slack, email) to keep everyone included.
  • Onboarding, training, and documentation built with distributed teams as the standard.
  • “Maybe we don’t need the face-to-face meeting...maybe just do it through an email thread or a Slack channel … It’s rethinking the problem.” — Ryan Montgomery [27:04]

3. Leadership, Vision, and Internal Alignment

• The Unique CEO/COO Dynamic:
  • Russell and Todd (Co-CEOs): Russell drives big vision and marketing, Todd handles tech; Montgomery bridges vision and operationalizing ideas.
  • The leadership adapts as the company grows: “We're a new company every six months.” — Ryan Montgomery [09:54]
• Staying Aligned:
  • Frequent “Go” (Goals and Obstacles) meetings for department heads to break down silos and maintain momentum ([29:39])
  • Commitment to “team number one”—executive team cohesion above functional lines (Patrick Lencioni’s influence).
  • Use of V2MOM (Vision, Values, Methods, Obstacles, Measures), a framework taken from Salesforce, to keep consistent goals documented and communicated ([36:24]).

4. Scaling Pains and Solutions

• Challenges of Rapid Growth:
  • Doubling/tripling size changes everything; management structure and leadership requirements keep evolving.
  • Compliance and platform requirements (PCI Level 1, etc.) added new hurdles as scale increased.
  • Need for new processes, hiring managers, and formalizing decision-making as team sizes ballooned ([13:27]).
• Adapting and Letting Go:
  • Leaders must let go of legacy ways of working and continually “throw away” methods that no longer serve the company at scale:
    • “There are these clear points where we as an executive team went through a transition together... We had to change how we thought about our company, about ourselves and the way that we interact.” — Ryan Montgomery [15:00]

5. Employee Engagement & Retention

• Focus on Meaningful Work:
  • Low employee turnover attributed to meaningful, exciting work and ownership culture—not free lunches or massages.
  • “The best stories, though, come from our employees and from a low, super low turnover rate. That, to me, is the key metric for are we doing a job of providing engaging work, interesting work?” — Ryan Montgomery [21:07]
  • Employees encouraged to take ownership, innovate, and influence product direction.
• Cultural Consistency:
  • Maintaining excitement about marketing and the product helped drive engagement and consistency despite rapid change.
  • Openness to new ideas from external hires helped fight stagnation and “managing for status quo.”

6. Building and Managing a Distributed Team

• Books and Influences:
  • “Remote” and “Rework” by Basecamp founders, “Play Bigger,” Patrick Lencioni’s leadership books, Salesforce’s V2MOM framework.
• Leadership Development:
  • Culture of continual learning via books and occasional outside consultants.
  • Leadership and employees encouraged to grow through exposure to new thinkers inside and outside the company ([19:18]).
• Meeting Rhythms:
  • Weekly “Go” (Goals and Obstacles) meetings with all directors for transparency and problem-solving ([29:39]).
  • All-hands “ClickFunnels Pulse” meetings for sharing updates, key metrics, and customer success stories ([44:10]).

7. Product Philosophy and Customer Feedback

• Focus on Simplicity:
  • ClickFunnels is intentionally not trying to be an all-in-one for every business need but stays focused on being “category king” in sales funnels.
  • Integrated with top tools in each category rather than trying to win all verticals.
  • Product roadmap increasingly reflects strong customer feedback loops and humility in switching direction when needed ([41:22]).
• Embracing Complaints:
  • “We love that they tell us exactly what they need and when we get it wrong. And we always listen to that feedback and internalize it and have invested heavily in making it right and making it simpler.” — Ryan Montgomery [04:29]

8. Giving Back and Company Purpose

• Sense of Mission:
  • Daily internal recognition of how ClickFunnels impacts the lives of entrepreneurs and small businesses.
  • Philanthropy: Support for Operation Underground Railroad, both in funding and operational support.

Notable Quotes & Memorable Moments

• On Remote-First Principles:
  “If you approach it from a remote-first, if you will, or distributed-first approach…think about, like, well, how are we going to build culture with a completely remote team? It'll work even if you are in an office, right?” — Ryan Montgomery [00:17]

• On Managing Fast Growth:
  “We're a new company every six months.” — Ryan Montgomery [09:54]
  “Every day we solve something, the next day there's this new thing that we got to worry about.” — Ryan Montgomery [11:46]

• On Culture and Engagement:
  “I think for me personally, if I were to summarize…how to build a company or how to run it, I am definitely focused on employees.” — Ryan Montgomery [20:18]
  “People can go work anywhere. Why are they choosing to work here?” — Ryan Montgomery [21:43]

• On Meetings:
  “Meetings don’t suck at all. You suck at running meetings.” — Cameron Herold [20:08]

• On Letting Go of Legacy Thinking:
  “A lot of that requires you throwing something away that's not going to help you get to the next level.” — Ryan Montgomery [15:27]

• On Focus:
  “We are the category king of sales funnels. We are not the category king of email autoresponders.” — Ryan Montgomery [41:21]

• On Patience and Perseverance:
  “I think a lot of people quit the day before it becomes the overnight success too, right? Yeah, it takes a long time.” — Cameron Herold [46:29]
  “Hang on a little bit, it’s going to show up. You just got to be patient. Keep putting yourself in the right position.” — Ryan Montgomery [46:26]

Key Timestamps

• 00:17 – Remote-first culture and why it works
• 02:35 – What is ClickFunnels? Product genesis and customer focus
• 09:54 – Company evolution every six months
• 13:27 – Growing from 6 to 70+ developers, hiring pains
• 14:36 – What’s changed and stayed the same as headcount grew from 30 to 350
• 18:44 – Personal development and leadership growth through books and consultants
• 21:07 – Employee engagement, low turnover, and meaningful work
• 24:32 – Lessons from “Remote” and “Rework”; practicalities of managing distributed teams
• 29:39 – Weekly ‘Go’ (Goals & Obstacles) meetings described
• 36:24 – Adoption of the Salesforce V2MOM framework for alignment
• 41:21 – Focus on being “category king” and integrating with others, not everything to everyone
• 44:10 – The ClickFunnels Pulse Meeting—daily metrics and sharing customer success stories
• 46:26 – Lessons Ryan would give his 22-year-old self on patience and positioning

Conclusion

This episode is a masterclass in scaling a distributed team, managing hypergrowth, and fostering a tight-knit, mission-driven culture—despite geographic barriers. Ryan Montgomery offers candid, practical wisdom on leadership, operational rigor, and remembering the human side of business at scale. Both new and returning listeners will find a wealth of actionable takeaways on culture, process, and the realities of riding the rocket ship of a bootstrapped SaaS success story.