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Unorthodox, Unapologetic, and Unmistakably Effective: Trenton Wisecup’s Rethink of High-Ticket Sales in Roofing - New York Tech Media

On the surface, Trenton Wisecup’s rise might sound like a classic Midwest success story: young hustler to multimillion-dollar closer; but dig a little deeper, you’ll find it’s anything but ordinary. Breaking into storm restoration roofing at just 19, he founded Arrow Roofing in 2017, and built it into a $5M+ company in just five years. Along the way, he earned top industry honors — NKL’s #1 Roofing Door Knocker, GAF Master Elite status, Haag cer…
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New York Tech Media broke the news in on Monday, July 7, 2025.
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