Using AI to Improve Lead Conversion with Justin Judd
Justin Judd explains how CHIIRP used AI-powered messaging to improve lead conversion, recover open estimates, and what 500 million texts reveal.
About This Episode
Justin Judd, VP of Sales and Partnerships at CHIIRP, joins Mustafa on the AI in Trades Podcast to talk about what nearly 500 million text messages reveal about how contractors win and lose jobs.
CHIIRP started as one operator's automated sales funnel and grew into a messaging platform for the trades. Justin shares what the data shows about follow-up timing and wording, which AI agents deliver results fastest, and where voice AI still falls short of a real conversation.
The bigger theme is that implementation fatigue is real, and chasing new tools is how contractors stall. Justin makes the case for committing to fewer things and actually finishing them.
Chapters
- 00:00 Introduction
- 00:25 Meet Justin Judd and CHIIRP
- 01:30 How Ruan Fenn built CHIIRP
- 03:22 Fenn's automated funnel that generated $2 million
- 05:17 How texting complements phone calls
- 06:58 What CHIIRP learned from 500 million messages
- 09:16 Quiz: The best time to follow up on open estimates
- 10:40 How small wording changes transform conversion
- 13:25 Launching and training AI messaging agents
- 15:10 Which AI agent contractors should deploy first
- 16:29 Where humans still outperform AI
- 20:00 The right role for voice AI today
- 23:00 Why contractors should stop chasing every new tool
- 25:30 How AI will change jobs and technician sales
- 29:09 How CHIIRP uses AI inside its own business
- 31:41 Making automated messages feel authentic
- 34:15 Why using ChatGPT alone is not enough
About the Guest
Justin Judd is the VP of Partnerships and a co-owner of CHIIRP, an AI-powered messaging platform for home service businesses. He has spent about 16 years in software, including helping Route grow to a billion-dollar valuation.
About AI in Trades
AI in Trades is a podcast from Peaka exploring how artificial intelligence is changing home services, field service operations, contractor growth, and the future of work in the trades. Each episode features operators, technology leaders, and business owners discussing practical ways AI is showing up in the field, in the office, and across trade businesses.
