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Home Service Expert

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

πŸ“… 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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