The Roofing Millionaires How Drones & AI Are Taking Over Roofing | TRM Episode 30 w/Jordan Milkie
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Sep 5, 2025 Jordan Milkie, co-founder of SKAI, dives into the transformative power of drones and AI in roofing. With a background in healthcare, he shares insights on how data-driven technologies enhance decision-making for contractors. The conversation highlights the unique advantages small startups bring through personalized service and the importance of user feedback. They also discuss the evolving landscape of drone regulations and the significant potential for growth as roofing companies embrace innovation. Jordan emphasizes the shift from reactive to proactive approaches, reshaping the industry's future.
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Data-Driven Offensive Strategy
- Sky captures high-resolution drone imagery over target zip codes so contractors can play offense instead of reacting to storms.
- They process gigabytes of images with AI to flag damage attributes and deliver an interactive platform for action.
Monetize Yearly Roof Imaging
- Offer proactive maintenance or subscription services to homeowners using yearly drone imagery as proof of roof condition.
- Charge a small monthly fee and use pre-storm images to simplify insurance claims and increase conversions.
Career Pivot To Roofing Tech
- Jordan shifted from healthcare consulting into roofing tech after a friend noted drones' potential and family roofing roots.
- They bought a drone, ran R&D, and rapidly developed Sky with direct industry input.
