Your Trusted Southwest Florida Roofing Experts
At Black Flag Roofing, our mission is to protect and strengthen our Southwest Florida community with roofs you can count on. We’re driven by our local roots, a commitment to quality that lasts, and a promise to treat every customer like family—because here, you are. From the first call to the final shingle, we’re here to deliver peace of mind, one home and business at a time.
At Black Flag Roofing, we understand that managing properties is about more than just buildings—it’s about protecting investments, maintaining trust, and ensuring long-term value. As industry veterans who built our company from the ground up, we’ve seen firsthand the gaps in professionalism and education in roofing. That’s why we provide a level of service that goes beyond just fixing roofs—we partner with property managers and portfolio owners to deliver proactive solutions, clear communication, and unwavering reliability.
When you work with Black Flag Roofing, you don’t get a revolving door of project managers—you work directly with the owners, ensuring expertise, accountability, and a commitment to excellence on every job. With deep roots in Southwest Florida, we’re not just another contractor; we’re a trusted extension of your team, dedicated to protecting your assets and making your job easier.
At Black Flag Roofing, we don’t just install roofs—we build lasting partnerships. Your properties, our priority.
A proud Texas transplant, Chris Little believes in doing things big—both in business and in life. As the co-founder of Black Flag Roofing, he’s earned a reputation as one of Florida’s most trusted roofers, building his company on integrity, craftsmanship, and genuine relationships. His commitment to top-tier service has made Black Flag Roofing a standout, ensuring every homeowner receives the quality and professionalism they deserve.
While roofing is his trade, Chris likes to joke that his true calling is the PGA Tour—though his golf game suggests otherwise. When he’s not leading projects or working closely with clients, you’ll likely find him on the course, perfecting his swing. Off the greens, he’s just as dedicated to his community, coaching youth football in Naples. For Chris, mentoring young athletes and instilling values of discipline, teamwork, and perseverance is just as rewarding as a perfectly built roof.
Whether he’s growing a business, chasing birdies, or shaping the next generation, Chris brings passion, precision, and just the right amount of Texas charm to everything he does.
A true Southwest Florida local, Spenser Pollard has always been deeply connected to his community. Whether volunteering at Bonita Springs art fairs or supporting locally owned businesses, he’s passionate about uplifting the people and places that make SWFL special.
Growing up, Spenser dreamed of being part of a close-knit community, and today, he’s built both his home and his business here. Through Black Flag Roofing, he channels that same passion into helping homeowners and business owners protect what matters most. His goal isn’t just to provide exceptional roofing solutions—it’s to make a lasting impact, just as so many have done for him.
When he’s not on a job site, you’ll find Spenser making the most of SWFL with his wife and son. Whether he’s attending local events, spending time on the water, or squeezing in a quick 18 holes, he’s always embracing what his hometown has to offer. For Spenser, Black Flag Roofing is more than a business—it’s a way to give back to the community that shaped him.
At Black Flag Roofing, we’re more than just roofers—we’re your neighbors, deeply connected to the communities of Southwest Florida. Born and raised in this sun-soaked, storm-tested region, we’ve built our business on trust, reliability, and a true passion for protecting the homes and businesses around us.
Serving Lee County, Collier County, and beyond, we bring a personal touch to every project, whether it’s a family home in Fort Myers or a commercial property in Naples. Led by owners Chris Little and Spenser Pollard, our team is committed to delivering durable, high-quality roofs that can stand up to anything Southwest Florida weather brings. Because here, a strong roof isn’t just an investment—it’s peace of mind.
