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How AI Is Closing Deals for Home Service Businesses with Chiirp (Ryan Fenn)

📅 March 27, 2026 ⏱️ 1:01:53 🎤 Ryan Fenn, Tommy Mello

Chapters

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  • 0:00
    Meet Ryan Fenn, founder of Chiirp
  • 3:18
    The garage-door side hustle origin story
  • 6:35
    Automation is simpler than contractors think
  • 13:04
    Training AI on the industry's best operators
  • 16:17
    Taking follow-up off the owner's plate
  • 22:50
    Why big companies win with automation first
  • 26:03
    Leaning into AI 100% as a competitive edge
  • 38:54
    Lead intent & training teams for rejection
  • 42:10
    Give power away to gain more power
  • 45:28
    Prove it in one market before scaling
  • 51:56
    Leading with appreciation, not force
  • 58:22
    The free AI revenue optimization analysis

Speakers

R
Ryan Fenn
CEO & Founder, Chiirp (SMS & automation platform for home services), Eagle Mountain, UT
T
Tommy Mello
Host / Founder, A1 Garage Door Service

Key Takeaways

Ryan traces his entrepreneurial start to a scrappy garage-door repair side hustle, making about $1,200 his first Saturday by offering both insurance-billed and cash service.

Most contractors overcomplicate automation: the real wins are simply contacting leads faster, following up more consistently, and triggering the right message at the right time.

Chiirp's AI is being trained on how the best operators work, letting a contractor effectively 'do it like Tommy does it' without building the playbook themselves.

The biggest value of automation is taking follow-up entirely off the owner's plate so they never have to wonder whether campaigns and nudges are actually running.

Lead source dictates approach: high-intent leads close around 92%, while social-media leads require a door-knocker mentality that tolerates more rejection and needs different training.

Ryan echoes the leadership principle that to gain more power you should give more power away, and that bringing on high performers multiplies the business.

Borrowing a lesson from CoreTech, he advises proving a new offering in one market and working through the bugs before scaling it across many markets at once.

Chiirp offers a free AI-driven revenue optimization analysis that studies a contractor's website and business to surface growth opportunities.

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