Roofing Experts

Jason Caguana

Sales Manager

Jason Caguana was born and raised in Rockland County, New York, where he grew up with his parents as the youngest of four siblings. Growing up, Jason developed a strong passion for football, a sport he enjoyed throughout his youth. During his teenage years, he played on several local teams, though some of his most meaningful moments came from playing with family on weekends. Outside of sports, his interests include writing, training, attending roofing expos and courses, traveling, and creating content. Coming from a family deeply rooted in the construction industry, Jason was introduced to the trade at an early age. At just 15 years old, he began working in restoration alongside his father and older brother. He spent weekends and school holidays gaining hands-on experience, steadily building a strong work ethic. Over time, he took on greater responsibilities, including communicating with homeowners, handling phone calls, signing contracts, and managing projects. Often serving as the primary English speaker on his team, he embraced this role with pride. These experiences played a significant role in shaping Jason’s character both professionally and personally. He developed strong communication skills and built relationships with business professionals, homeowners, colleagues, and educators. This ability to connect with others not only made his work more enjoyable but also helped him grow socially and professionally. In June 2022, Jason graduated from Spring Valley High School. He continued working in the construction field while attending college to study accounting. However, after gaining further experience and discovering new opportunities, he made the decision to pause his education and fully commit to pursuing a career in a new area of the roofing industry. In 2025, Jason served as the general manager of his older brother’s roofing company. In this role, he oversaw administrative operations, production, and appointment setting, gaining valuable insight into how a business operates on both a daily and long-term basis. This experience solidified his ambition to become a full-time salesman. Today, Jason continues to grow within the industry, focusing on expanding his skills and expressing himself through his work. He recognizes that his abilities were developed over time through dedication and persistence. He lives by a personal quote he created: “You’re only as good as your last one. After everything—my hard work, focus, and dedication—that’s where my confidence comes from.” This mindset continues to guide him through both the highs and lows of his journey as he works toward his long-term goals.