Serve, Automate, Scale: Ryan Fenn on Building Chiirp and Transforming Contractor Sales
Update: 2025-07-05
Description
In this episode, Sam Wakefield sits down with Ryan Fenn, founder and CEO of Chiirp, to unpack the powerful intersection of technology, faith, and service in the trades.
From repairing windshields to scaling an 8-figure SaaS platform used by thousands of contractors, Ryan shares the real story behind Chiirp’s rise—and how automation is changing the follow-up game forever.
If you’re in home services and struggling to keep up with follow-through, this episode will shift your mindset and your method.
🔑 What You’ll Learn:
- Why Ryan started Chiirp (and how it almost didn’t happen)
- The #1 follow-up mistake most contractors make
- How automation + authenticity = scalable trust
- The mindset shift that took Ryan from burnout to breakthrough
- Faith, family, and leading with purpose in a performance-driven world
📲 Learn more about Chiirp → https://www.chiirp.com
💬 Want to build a follow-up system that actually closes?
Coaching & Training → https://www.closeitnow.net/coaching
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