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

2026-03-27

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Ryan Fenn is an entrepreneur and the founder and CEO of Chiirp, a software company focused on helping home service businesses convert more leads into booked jobs. A lifelong entrepreneur, Fenn built his career from the ground up—starting with a windshield repair business he launched with just a few hundred dollars and scaling it into a multi-location operation. Through his early experience in sales and home services, Fenn identified a major gap in the industry: most companies weren't losing revenue because of poor marketing, bu...

Ryan Fenn is an entrepreneur and the founder and CEO of Chiirp, a software company focused on helping home service businesses convert more leads into booked jobs. A lifelong entrepreneur, Fenn built his career from the ground up—starting with a windshield repair business he launched with just a few hundred dollars and scaling it into a multi-location operation.

Through his early experience in sales and home services, Fenn identified a major gap in the industry: most companies weren't losing revenue because of poor marketing, but because of inconsistent and slow follow-up with leads. This insight ultimately led him to create Chiirp, which automates customer follow-up across multiple channels, including text messages, emails, voicemail drops, and more.

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