AI removes guesswork from roofing customer outreach

By Jesse Sanchez. 

Machine learning, demographic data and high-resolution imagery help contractors target homeowners with real roofing needs. 

Marketing conversations in roofing are increasingly shaped by data and artificial intelligence and Reworked.ai is positioning itself at the center of that shift. During this episode of Roofing Road Trips®, Karen Edwards spoke with the company’s co-founders Fred Castonguay and Shyam Prabhakar about how technology can help contractors sharpen outreach strategies and improve conversion rates. 

Reworked.ai was built around a simple but persistent industry problem. Contractors spend heavily on marketing yet often struggle to identify which homeowners are most likely to need roofing services. Fred traced the idea back to his experience in real estate investment and a conversation that challenged traditional outreach models. He recalled, “There’s got to be somebody that’s using machine learning to make a more accurate prediction of who you should be reaching out to, to help you eliminate the guesswork in your customer acquisition process.” 

That insight led Fred and Shyam to rethink how contractors approach marketing. Rather than targeting entire counties or zip codes, Reworked.ai focuses on identifying homeowners with a high likelihood of roof failure and the financial profile to act. Fred explained, “We’re not identifying intent, we’re identifying need.” 

Behind the scenes, the platform relies on large-scale data analysis. Shyam described the challenge of moving beyond assumptions and bias to build reliable predictions. “One of the hardest parts about building this business at the offset was actually cracking the how,” he said, noting the use of demographic attributes and historical permit data to create individual homeowner scores. 

A key component of that process is imagery. Reworked.ai works with Eagleview to evaluate roof conditions using computer vision. Fred emphasized why that matters to contractors, “They are finding the bad roof,” he said, adding that the system flags signs of end-of-life conditions contractors already recognize in the field. 

The result is a self-serve platform that allows roofers to upload existing lists, generate new opportunities by geography or pull individual roof reports. Contractors receive prioritized spreadsheets rather than generic lists, helping them concentrate outreach and improve efficiency. 

As marketing costs rise and digital channels grow more competitive, Reworked.ai’s founders see targeted data as a practical advantage. “The only wrong way is not to do anything,” Fred said, pointing to the importance of consistent outreach backed by better information. 

Listen to the podcast or Watch the conversation to learn more about how Reworked.ai uses AI and data-driven insights to help roofing contractors connect with homeowners who have real roofing needs!