Building AI Agents Trained on Real Contractor Conversations
How many leads are slipping away because your team didn’t respond quickly or follow up consistently? Contractors invest heavily in generating opportunities, but even strong leads can go cold when communication is delayed or when your messaging is off. The challenge is not just automating more messages. It is creating communication that feels relevant and effective at scale.
In this episode of Cracking The Code, Ryan Fenn, CEO of CHIIRP, explains how AI agents trained on real contractor conversations can help businesses improve response times, strengthen follow-up, and convert more opportunities without making the customer experience feel robotic. He breaks down how specialized agents can be trained for individual lead sources and why changing only a few words can dramatically affect customer response. Years of real communication data is helping contractors build smarter systems that support their teams and scale authentic conversations.
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00:00:00:01 – 00:00:13:15
A lot of AI companies are trying to train AI so you can fire more people. We’re trying to train AI so you can hire more people and turn them into superhumans.
00:00:13:17 – 00:00:40:15
Welcome back to Cracking the Code, Man. Today’s conversation is one that hits right at the heart of what I believe is one of the biggest missed opportunities in the home service industry. Most contractors think they have a marketing problem, when in reality they’ve got a follow up problem. Chirp is helping contractors automate conversations across text, email, voicemail, and now AI so they can scale relationships, not just transactions.
00:00:40:15 – 00:01:01:02
So Ryan, welcome to Cracking the Code. Thank you David. Appreciate it. Appreciate it. Super happy to be here. Today’s consumer is pretty open to filling out a form right. They really are. So the concept of that immediate text message hey I’m I’ll call you back and just a little bit on another call. But if you want to go ahead and schedule right now, here’s a link to a form.
00:01:01:02 – 00:01:21:17
You can go ahead and go ahead and get on our schedule right away. That actually is going to take out a ton of people that were on the fence or, you know, like, I don’t know if they’re really going to call me back out of, you know, all that concern of what the typical contractor operation looks like. That part I think is, is gold, right?
00:01:21:18 – 00:01:49:00
That’s gold. But, you know, a lot of guys that I talk to are like, you know, they hear the word automation and they think that’s going to feel robotic. You know, kind of thing. And it’s like, so you talk about scaling authenticity, not replacing it. How do you guys use automation to, you know, come alongside that concern. Contractors feeling all, you know robotic.
00:01:49:00 – 00:02:12:06
It’s like it’s just not that way. Well, for me, authenticity is the key to business. It’s really difficult to scale authenticity because, you know, when you’re when you’re small, you’re the guy answering the phone. But the moment you scale your business, that goes away very, very quickly because now it’s we and it’s us, and it’s 6 or 7 layers away from the guy, right?
00:02:12:07 – 00:02:31:02
It gets very challenging to tell your story at scale, because the story to me is the key to business. When we talk, when we talk about authenticity, that’s your story. How do you do that at scale? Let’s say you’re doing 10 million. You know, you got several leads coming in every day. There’s no way you’re going to pick up the phone as the owner and call each of these leads.
00:02:31:04 – 00:02:50:06
But imagine if you could immediately text them, introduce yourself, and then send a video of you talking to them, you know, saying, and this is not an AI produced video. I want people to think it’s AI. This is you doing a video and you basically just say, I want to say thank you, I want to I wanted to tell you, thank you for the opportunity for us to earn your business.
00:02:50:06 – 00:03:14:05
So let’s say like somebody fills on Angie form, right? And, you know, Angie leads are notoriously harder to convert. Imagine if you were the first text message to go out and you created a human response like a human emotion, before the others even had a chance to call or text. And now they get a video of, of of you saying, hey, thank you so much.
00:03:14:06 – 00:03:38:11
Appreciate you checking us out. That will create a human emotion, an attachment that the other guys can’t do because they’re calling in and just going. They’re just doing the price thing, right. Let’s say they don’t convert on on attempt one. We’re going to follow up for 14 days or more with not just, hey, just following up, just following up, just following up.
00:03:38:12 – 00:04:03:03
We’re going to also drip like, hey, you know, Jennifer in your area also had this problem and she left us this five star review wanted you to check it out. You know, little things that that tell your story more along that process and create those human responses. So you brought up two things. One is you brought up Angie’s List as a lead source.
00:04:03:04 – 00:04:25:02
Right. And so clearly with AI, you can know the lead source. And you could even dial up the right video to say, hey, you’re really smart. So I’m now David Holt at Holt Service Company. Hey, Ryan, you’re really smart to use Angie List as a source, because you know what? Some of our very best customers have come from Angie List, so you could tie it to what they’ve already chosen.
00:04:25:02 – 00:04:45:23
Right? And you’re paying them on the back. You’re giving them some emotional feedback, right? You’re giving them some love for doing the right things. And so that’s one step, which would be really cool to kind of personalize it. And again, but am I sure I’m not talking to AI Ryan or is this AI David. You know. Anyway, but I got to make sure you look like the guy I saw last week.
00:04:46:00 – 00:05:13:00
That’s pretty good that AI is getting really good, but that’s one piece. But then the other side of it, if they filled out a form, then probably you do have their street address. And if you had a really cool database full of area based testimonials, you could even say, hey, and here’s a link to a testimonial from a person that lives in your same neighborhood that had some of the same problems that you may be experiencing.
00:05:13:00 – 00:05:35:06
You’d love to, you know? I mean, I’m just sitting here, my head’s just going boom. I’m just like, what in the world? But that’s where AI can really come in. And that automation and AI is not necessarily being the video. It’s not being the audio. It’s trying to bring the human elements that you’ve. Now we can say it canned.
00:05:35:07 – 00:06:00:00
We’ve now recorded it and delivering it, serving it up in a way so that AI is actually feeling more human, not less. That’s right. And you nailed it when you said the Angie lead type of thing can be trained. So so when we talk about that, we have within Chirp, we have the agent network. So you would have an agent that’s specifically trained for Angie leads only.
00:06:00:00 – 00:06:23:00
That’s it. So now, like you said, when an Angie lead comes in, we trigger the Angie specific agent and follow up designed specifically for that thumbtack. We’d have a different one. Your website. We’d have a different one. Google, LSA, Facebook lead forms, all these different things. We have differently trained robots to do the right thing for that specific lead source.
00:06:23:00 – 00:06:47:07
So an AI agent, when Ryan’s talking about that is like, you’ve hired this digital employee to handle an Angie list lead properly. The beautiful thing about an AI agent, as long as the power is up and the internet is working, we’re good. That AI agent will not call in sick and they work 24 hours a day, seven days a week for the same price.
00:06:47:07 – 00:07:04:11
It’s an amazing thing. Yeah. So now you say, okay, cool. If I was to get it’s like. It’s like you can like it’s like going to Willy Wonka, like, you know, you can everything you can eat, like all the candies there you can choose and now you can look at it and just go, okay, I want an employee.
00:07:04:15 – 00:07:26:23
We can get really specialized employees. I’m going to specialize them for Angie Leads. That’s it. That’s all they’re trained to do. That’s all I want them to do. And they’re just going to sit there. And when an Angie lead comes in, they’re going to work on conversion. Now here’s the here’s where it gets really, really fun. We have seven years of data that we’ve been building up where text messages have been going out and coming in.
00:07:26:23 – 00:07:48:10
So we have hundreds of millions, if not billions of dollars sold through the church system. And now we have AI being trained off of those messages. And it’s going, what? What’s been the best sequence? What’s been the best thing to say, the best words to use when an Angie lead happens? What’s the best thing to say when a thumbtack lead happy?
00:07:48:11 – 00:08:09:00
Now these agents that you’re hiring as employees are trained by seven years of data to do the thing correctly. So now you’re not having a guess. Like, what should I say? What should I do? You just go cool. I just hired a highly specialized AI agent for Angie Leads who’s trained on seven years. I’ll let her do her thing.
00:08:09:00 – 00:08:36:16
Now. I got one for thumbtack, I got one for LSA, and. And they’re doing what is what the biggest contractors over the last seven years have been doing to convert these leads. Now you just get to take advantage of that. The beautiful thing about what you’re doing is you’re actually mining the wisdom of the crowd, right. So we got this, but it’s now the wisdom of the cloud because it’s all in this cloud database that you’ve built and collected over the years from all these contractors.
00:08:36:16 – 00:09:04:12
And you take that wisdom and compact it into this agent, this digital employee sitting there just munching on all this wisdom. Right? And it’s like, Ali, how cool is that? So thinking about the real world contractors, looking at it through the AI digital eye that you’re seeing right now, what does it look like for the next 12 to 24 months, or is that too long to look ahead because things are changing.
00:09:04:12 – 00:09:23:00
So Dagenham quick, I mean, it might be the next 12 or 24 minutes. What do you what do you see? What we’re finding is kind of like where the honeymoon time is kind of starting to wear off a little bit, where everybody kind of had this like, whoa, this AI is crazy. They all, all the all their AI knows them.
00:09:23:00 – 00:09:45:11
They’ve been chatting with it like they use it for their therapist and like all this stuff. Okay, we’ve gotten past the, like, hype and the excitement of it. Where does it now actually affect businesses? Where can we actually make money with it? Where can I actually work? Data is going to be the big differentiator. We have over half a billion text messages sitting there of actual human conversations.
00:09:45:11 – 00:10:14:02
And so that’s the that’s going to be I think the next big play is companies looking at this going, okay, cool. You have AI. Is it specialized AI. Is it dialed for what I need it to do? Because anybody can wrap up ChatGPT and it’ll just be the same thing as everybody else, right? The fact that you’ve been collecting all this information, I mean, you have a gold mine for contractors that want to access that knowledge base and be able to implement that in their business.
00:10:14:03 – 00:10:32:16
I mean, that’s that’s congratulations, man. This is a big pivot from fixing chips and windshields, Yeah, 100%. Well, let me let me let me tell one story of that so that this all ties together under why I think this is so important. I used to do windshield repair. That was my first business, and I did it door to door.
00:10:32:16 – 00:10:48:20
I started doing it door to door. And then I saw a girl doing it at a gas station and I thought, dang, she’s smart because like, cars are coming to her. I’m going out looking for cars. Cars are coming to her. So I go to the gas station and what she was doing, she was washing people’s windshields as a courtesy.
00:10:48:20 – 00:11:05:00
And then and then that gave her the opportunity to look for chips in the windshield. Right. And and so I go to this local gas station, I say, hey, I want to do this. He says, go for it. And I start asking people as they pull him and say, welcome to Mike Chevron. Can I wash your windshield today?
00:11:05:00 – 00:11:28:17
No, no, no thank you. No thank you. Nine out of ten would say no. So I was I was there was 100 cars. If I see 100 cars ten people say yes, three people have chips. I gotta close all three just to survive. So I knew some. I knew I had to change something. So I started to work with the words that I was saying to the customer when they came in, and I changed from, can I wash your windshield today?
00:11:28:17 – 00:11:52:08
To as a courtesy, we’re washing everybody’s windshields. That was it. When I changed just those few words, I went from looking at ten windshields from one out of ten, saying yes to nine out of ten saying yes. And now I have out of 100 cars, 90 opportunities versus ten. So nine times the opportunity with the exact same amount of traffic.
00:11:52:08 – 00:12:15:08
So this goes back to the marketing. You’re getting a certain number of leads or you saying the right things to open up opportunity or close the door on opportunity. And it could be the difference of 1 or 2 words in a text message you send. And that’s where the value of this AI is coming in, is because we’re able to look and say what messages are getting yeses and what messages are getting knows.
00:12:15:08 – 00:12:47:00
And now we can actually analyze and figure out what’s working. But here’s the deal, guys. You don’t need more leads to grow your business. Same hundred windshields, right? You just need to do a better job with the leads you already have. You need to communicate properly. That’s what it’s really all about. Because the truth is, every missed call, every unreturned estimate, every slow response, every windshield that you didn’t get to inspect is not just a missed opportunity that’s lost revenue sitting right inside your business.
00:12:47:00 – 00:13:13:07
And what I appreciate about what you’re doing, Ryan, with chirp is this it’s not about replacing people. It’s about helping great companies show up consistently, respond faster, and build better relationships at scale. That’s right, that’s right. So Ryan, thanks for coming on, man. Sharing your story and helping our audience think differently about one of the most important levers in their business.
00:13:13:07 – 00:13:32:05
And to everyone listening. If you got value from this episode, make sure you share it with someone in the industry who needs to hear it. This is important. We’ll see you next time on cracking the code. Ryan. Last word. So thank you so much David. Appreciate it. If anybody wants to connect with me, add me as a friend on Facebook, Ryan Finn.
00:13:32:05 – 00:13:53:19
And of course, if you’d like to check out chirp, head on over to With Two Eyes. I book a demo and what we do is we like to dive in and just find those leaks in your business and implement really easy automations to start so that we can we can increase your conversion rate very quickly and find that low hanging fruit.
00:13:53:19 – 00:14:06:20
So check us out. We’d love to. We’d love to help you out. Yeah. Make sure when you do sign up for that demo that you tell them you heard about it. On cracking the code. We create the opportunity, guys. Have a great day, man. We’ll talk to you soon. Thanks, Dave. We’ll see you.
