In this exclusive interview with CanadianSME Small Business Magazine, Trenton Wisecup, Founder and CEO of Arrow Roofing, shares the strategies behind his company’s rapid growth, taking it from a startup to an 8-figure revenue business in just seven years. Under Trenton’s leadership, Arrow Roofing has become a trusted name in Michigan, serving over 2,000 homes and gaining recognition from major media outlets like Forbes and Yahoo Finance. Passionate about mentorship and community, Trenton is committed to helping fellow roofing business owners thrive through active involvement in organizations like the National Roofing Contractor Association. As Arrow Roofing aims for $30 million in revenue, Trenton’s approach focuses on sustainable, values-driven growth backed by strategic systems and technology.
I’m Trenton Wisecup, leading the charge at Arrow Roofing. In just seven years, we’ve gone from a small startup to generating 8 figures in revenue. It all started with a clear vision and strong core values. Since then. Arrow Roofing has become well-known & has served over 2000 homes in Michigan.
You’ve grown Arrow Roofing from a small startup to an 8-figure revenue company in just seven years. What key strategies and decisions contributed to this rapid growth, and how do you see these strategies evolving as you aim to surpass $30 million in revenue?
Growing Arrow Roofing from a $20 startup to an 8-figure company in just seven years took a mix of relentless discipline, strategic scaling, and deep industry understanding. One of our pivotal strategies was embracing the storm restoration niche early on, especially after my breakthrough success in Texas. From there, I applied my knowledge as an insurance adjuster to create a streamlined, client-first service. We scaled by reinvesting in talent, securing Haag certifications, and earning key distinctions like GAF Master Elite and A+ BBB ratings, all while staying rooted in community values.
We also prioritized automation, building systems that allow our business to run efficiently without needing me in every step what I call the “Hit by a Bus” test. As we aim to surpass $30 million in revenue, the strategy evolves: we’re doubling down on technology, mentorship through EmpowerMe Consulting, and strengthening our leadership pipeline to support scalability. Our goal isn’t just revenue growth it’s sustainable, values-driven impact backed by systems that can weather any storm.
Arrow Roofing is recognized for its expertise in handling insurance claims, which is a critical aspect of the roofing industry. Can you share some best practices or innovations you’ve implemented to streamline the claims process and ensure fair settlements for your clients?
Insurance claims are one of the most complex aspects of roofing, but they’ve become a core strength for Arrow Roofing. Our edge lies in understanding the process inside and out thanks to my background as an insurance adjuster. We’ve trained our team on the nuances of storm-related damage assessment, using Haag-certified inspectors to ensure accuracy and legitimacy. This not only speeds up the claims process but also builds trust with insurance carriers.
We’ve also adopted cutting-edge technology that allows for real-time communication with insurance companies and clients. Drones, photo documentation apps, and smart inspection tools provide visual proof, minimizing disputes and accelerating approvals. Clients often feel overwhelmed dealing with insurers, so we act as their advocates helping them navigate paperwork, understand deductibles, and access financing through platforms like GAF Smart Money.
What sets us apart is our proactive, transparent communication and tech-enabled process. We don’t just react to claims; we educate homeowners and walk them through each step. This ensures timely settlements and a positive experience—turning a stressful situation into a trust-building opportunity.
You’re actively involved in mentoring and supporting fellow roofing business owners. How do you approach leadership development within your own team, and what advice would you give to entrepreneurs looking to build a strong leadership culture in their businesses?
At Arrow Roofing, leadership isn’t a title it’s a mindset. Developing leaders starts with instilling ownership, purpose, and clear values from day one. We believe in empowering our team to think like entrepreneurs, whether they’re on the roof or in the office. I draw from my experience mentoring 20+ roofing business owners through D2DExperts, applying those same frameworks internally. We focus on communication, accountability, and continuous improvement.
We foster leadership by providing structured mentorship, measurable KPIs, and autonomy within defined systems. Tools from EmpowerMe Consulting help our team members grow in confidence and capability whether it’s mastering sales scripts or leading crews in the field. I also believe in leading by example showing grit, consistency, and vision, even during challenging times.
For entrepreneurs building a leadership culture, my advice is simple: start with clarity. Define your mission, empower your people, and hold them accountable with compassion. Create systems that reward initiative and offer space to fail forward. Leadership grows in environments where people feel trusted, challenged, and valued. Build that environment, and your company will grow with it.
The roofing industry is increasingly leveraging automation and technology to improve efficiency. How has Arrow Roofing incorporated automation tools into its operations, and what benefits have you seen in terms of productivity and customer satisfaction?
Automation has been a game-changer for Arrow Roofing, helping us streamline operations while enhancing client experiences. We’ve integrated CRM systems, digital scheduling, and workflow automation tools that track every stage of a roofing project from the first inspection to final invoicing. This level of organization reduces delays, errors, and miscommunication.
One of our biggest wins came from automating our follow-up systems, which increased client satisfaction and conversion rates. Whether it’s reminding a homeowner about documentation or scheduling post-installation inspections, these touchpoints are no longer reliant on manual effort. Our team can now focus more on delivering exceptional service and less on repetitive tasks.
We also use tech for accurate roof measurements, real-time damage assessments, and instant quote generation. These innovations not only speed up internal processes but give clients faster, clearer information building confidence and trust. Tools like GAF Smart Money allow seamless financing, making premium solutions more accessible.
The result? Projects move faster, clients are more informed, and our team stays focused on high-value tasks. Automation doesn’t replace our people—it empowers them. That’s how we maintain excellence while scaling rapidly in a competitive market.
As a successful entrepreneur with a strong track record of innovation and growth, what final thoughts or advice would you offer to small and medium-sized business owners looking to achieve sustainable success and resilience in their industries?
If there’s one thing I’ve learned on this journey, it’s that success isn’t about working more it’s about working smarter and building a business that thrives without you. For small and medium-sized business owners, resilience starts with a clear vision, solid systems, and the right people. You need to focus on building something that can pass the “Hit by a Bus” test where your business can run without constant firefighting.
My advice? Invest in your culture first. Define your values, and make sure every hire, process, and system reflects them. Embrace automation and data use KPIs not just to track growth but to identify where you’re winning and where you need to improve. And never stop learning. Whether it’s through mentorship, masterminds, or programs like EmpowerMe Consulting, surround yourself with people who push you to grow.
Also, don’t underestimate the power of customer trust. In industries like roofing, reputation is everything. Deliver value consistently, communicate clearly, and stand by your work. If you build with intention, adapt with courage, and lead with integrity, sustainable success will follow.
