Using AI to Improve Lead Conversion with Justin Judd
Justin Judd of CHIIRP on using AI-powered messaging to improve lead conversion, recover open estimates, and what 500 million texts reveal about timing and wording.
About This Episode
Justin Judd, VP of Sales and Partnerships at CHIIRP, joins Mustafa to talk about how AI is changing customer communication in home services in the fourth episode of the AI in Trades Podcast. Justin shares how CHIIRP grew from an operator's automated sales funnel into a messaging platform built for contractors, and how the company is now using nearly 500 million text messages to train AI agents.
The conversation explores what this data reveals about conversion, including the best time to follow up on open estimates and how small changes in wording can dramatically affect results. Justin also explains where contractors should deploy AI first, why agents specializing in missed-call and estimate follow-up can deliver immediate value, and where humans still outperform voice AI.
They also discuss implementation fatigue, AI-assisted technician coaching, changing job requirements, and how CHIIRP uses Claude to find bugs and accelerate software integrations. Throughout the episode, Justin emphasizes that technology works best when contractors commit to implementation instead of constantly chasing the next tool.
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.
