At the age of 21 and with just $1,400 in hand, Trenton Wisecup founded Arrow Roofing Services in 2017. Fast forward to today, the company’s revenue has skyrocketed to an astonishing $5 million, with projections to quadruple that in 2024. However, Wisecup’s vision extends far beyond his own company. For him, it’s about revolutionizing the roofing industry and giving fellow roofers the tools to thrive in an ever-changing landscape.
Recognizing the need for adaptability in the roofing industry, Wisecup has shifted his focus towards storm roofing, to equip all retail roofers with the tools and knowledge they need to to transition seamlessly into the “recession-proof” space.
By providing the same comprehensive training, including systems, standard operating procedures (SOPs), and contracts, that has allowed his own team to be so successful, Wisecup empowers other roofers to navigate the complexities of the storm roofing business with confidence.
“I give them a systemized, implementable playbook so that they can mimic it, copy it, use it, change it, whatever they want to do,” he explains.
But beyond just technical skills, Wisecup emphasizes the importance of building a strong company culture and nurturing effective leadership. Through his coaching program, roofers learn how to create an environment that fosters teamwork, innovation, and positivity—aspects of business that he believes strongly in.
“But the bigger, deeper aspect of it all is teaching these guys how to be strong leaders and create an amazing company culture, and then having the appropriate and healthy positive mindset to succeed. That is my wheelhouse,” he continues.
Wisecup’s expertise in building culture and developing leaders sets the foundation for long-term success in the roofing industry. After all, he expanded his team at Arrow Roofing Services from one person to eight, establishing a strong culture of collaboration and support, which has allowed his team to win awards, including first place at the 2023 National Knocking League.
However, Wisecup admits that transitioning to storm roofing comes with its own set of challenges, from navigating insurance processes to estimation software like Exactimate. “It’s definitely a big mindset switch,” he says. “A lot of people are super scared of the storm space. They don’t know how to identify the damage, and because they don’t know how to identify the damage, they don’t know how to effectively communicate and explain it or justify it.”
He continues, “the estimating process is very advanced and so the pain of having to learn that can cause a lot of anxiety. That pain to a lot of people looks worse than the pain that they’re experiencing from their business, so instead of dealing with the pain to grow, they’re dealing with the pain of complacency. And so it’s just like, which pain do you want to deal with? It’s up to you.”
By addressing common pain points and setting clear expectations, Wisecup ensures that roofers are equipped to tackle challenges head-on. He provides guidance and support to help them overcome these obstacles and thrive in the storm roofing sector.
“We make sure that you’re aware of everything you need to know and that we’ve given it to you in a digestible way. Then, we ask that you lean on us, lean on the program, the videos, the documents, the information funnels. We’re right there making sure that one has the support if they need it,” Wisecup says.
With a clear endgame in place—to become nationally recognised in the door-to-door space—Wisecup intends to continue to mentor and coach other roofers, conduct speaking engagements, and lead training programs that will bring new ideas and innovation to the roofing industry. He is passionate about helping others reach new heights, just like Arrow Roofing Services has. They are a part of the 1% Master Elite Contractors with GAF, and members of the National Roofing Contractor association.
From starting with just $1,400 to scaling his business to unprecedented heights, Wisecup has learned invaluable lessons along the way. His willingness to embrace change, overcome challenges, and invest in the success of others sets him apart as a visionary leader in the roofing industry.
“I just want to help people,” he says. “I want to bring more value to roofers.” As Wisecup continues to revolutionize the roofing industry and empower fellow roofers to succeed, his impact will surely be felt for years to come.
