TOGETHER WE GO FURTHER

Our Manifesto

Forged in grit, built with precision, and driven by legacy—Roof Rider Academy is where ambition meets mastery. We don’t build businesses by chasing success; we engineer momentum and carve the path. For industry leaders who refuse to be ordinary—who move with purpose, build with intent, and refuse to trade their time for chaos—we craft the SOPs, workflow charts, and systems that transform the daily grind into seamless execution. This is more than strategy—it’s craftsmanship, the art of scaling with vision, and the power of leaving an industry better than we found it. Because true pioneers don’t just follow trails—they blaze them.

Dream Bigger. Forge Your Path.

Matthew Szostek

COO Founder

With a background in the U.S. Navy’s nuclear power program on submarines, industrial power distribution, and quality assurance, Matt has spent a lifetime mastering complex systems. His expertise spans specialized industrial fields, from control electronics to metal fabrication, team leadership, and structural art. A natural problem solver, he excels at designing and interpreting intricate systems, seamlessly operating both within and beyond conventional specifications to deliver innovative solutions.

Now, he’s bringing that same level of precision and problem-solving to the insurance industry. Recognizing its outdated and often unfair structure, he’s on a mission to revolutionize the field—pioneering a future where claim settlements are transparent, efficient, and just. Clients working with him don’t just get results; they gain a renewed purpose and a fresh perspective on solving problems they once thought impossible.

At his core, Matthew believes in relentless improvement: “Do it better.” Whether it’s refining his own methods or helping others break through roadblocks, he approaches challenges as puzzles waiting to be solved. Where most people see obstacles, he sees opportunities. The truth drives his work, and his commitment to finding solutions—no matter how complex—ensures that no problem remains unsolved.

Lisa Cimaroli

CEO Founder

Driven by legacy, Lisa Cimaroli is a powerhouse in the insurance and exterior restoration industry. With over $80 million in career sales, she has redefined success—not just in business, but in leadership, strategy, and impact.

As the former founder of CornerStone Restoration LLC and Guardian Exteriors, Lisa carved her place in an industry where precision, execution, and advocacy matter most. But success wasn’t enough. She saw a gap—contractors and public adjusters struggling to scale, trapped in inefficiencies, and missing the systems needed to build lasting legacies.

That’s why she helped built Roof Rider Academy—not just a consulting firm, but a movement. A place where industry leaders master their craft, sharpen their edge, and transform their businesses with strategy, workflows, and execution.

Hayleigh Sanchez

Vice President

Hayleigh Sanchez has built a career in high-stakes industries, from customer service and insurance roofing to adjusting and supplementing for major restoration firms. Her defining strength? Reasoning with the unreasonable. Where others back down from difficult conversations, she navigates them with sharp intuition and an unshakable presence. Fear—whether of failure, conflict, or risk—doesn’t hold her back. She has stared down defeat and walked away victorious.

Now, as a driving force behind Roof Rider Academy, Hayleigh is on a mission bigger than business. She’s building a future her son can be proud of—one that proves no starting point is too small to rise from. She leads by example, showing clients that success isn’t about where you come from, but where you’re willing to go. Her energy is infectious, giving those around her a renewed sense of purpose and a belief that if she can overcome obstacles, so can they.

For Hayleigh, quitting has never been an option. She believes in relentless persistence—tomorrow always holds another opportunity to push forward, improve, and break through limits. Her advice to others is simple: keep moving toward the future, even when you can’t see the full path. Guided by intention and sheer willpower, she has built something extraordinary, and she’s just getting started.

Leave It Better Than You Found It

Building Strong Foundations with Systems and Networks

JobNimbus

EagleView

American Policyholders Association

Cohen Law Group

All Claims Public Adjuster

X-Build

At Roof Rider Academy, we don’t just work in the industry—we shape its future. Our team collaborates with top organizations like JobNimbus, EagleView, PayPixl, Cohen Law, Estimate Mastery, IKO, All Claims Public Adjusters and the American Policyholders Association (APA) to drive innovation, improve efficiency, and set new standards for excellence in restoration.

As a collective force, we are committed to education, advocacy, and raising the bar. Lisa has given her knowledge freely a several speaking engagements including major industry events like RoofCon, SRC Summit, JobNimbus Summit, Estimate Mastery Summit, and Honest & Ethical Storm Domination with Cohen Law, together we bring real-world strategies, workflow solutions, and leadership insights to the professionals shaping the future of this space.

Our leadership is felt industry-wide. As a team, we serve on key industry boards, mentor the next generation, and advocate for policyholder rights. Lisa Cimaroli, serves as the Chairwoman of North Florida’s National Women in Roofing and is a Corporate Member and Speaker for the APA. Matt and Lisa were honored as Advocates of the Year for the American Policyholders Association. Lisa has also been recognized as 17th in the Nation for FORBES 2025 Entrepreneur of Impact. All team members hold elite certifications as IKO Craftsman Premier Installers and Xactimate Level 2 Specialists.

But beyond the accolades, our mission is clear: leave this industry better than we found it. Through education for homeowners and businesses, industry transparency initiatives, and systems that allow contractors to scale smarter, Roof Rider Academy is leading the charge for a stronger and more ethical restoration industry.