The Home Service Expert Podcast

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

14 snips
Mar 27, 2026
Ryan Fenn, entrepreneur and CEO of Chiirp who scaled a windshield repair startup into a multi-location business. He reveals how rapid, multi-channel follow-up and wording A/B tests turn leads into booked jobs. Hear how AI and huge messaging datasets refine timing and phrasing. Learn why simple automations, video texts, and training teams unlock scalable, outcome-focused growth for contractors.
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ANECDOTE

Gas Station Pitch That Scaled A Business

  • Ryan Fenn grew a windshield repair business from door-to-door and gas-station setups into multi-location operations using quick follow-up and simple positioning.
  • A wording change from “Can I wash your windshield?” to “As a courtesy, we’re washing everybody’s windshield today” increased yes responses from ~10% to ~90%.
INSIGHT

Speed-to-Lead Multiplied Ad ROI

  • Immediate follow-up — texting a lead within a minute — transformed Ryan's ad ROI from unprofitable to 8–10x return on ad spend.
  • He built automations combining multiple tools to text instantly and follow up consistently across channels.
ADVICE

Stop Chasing Leads Fix Follow Up First

  • Fix follow-up before buying more leads because inconsistent or slow follow-up is often the real revenue leak.
  • Test message wording aggressively (A/B test) to find the combinations that lift conversion by large margins.
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