Meet Black Flag Roofing, Owner-Led Roofers in Southwest Florida
Black Flag Roofing is a locally owned roofing company in Naples, where co-founders Chris Little and Spenser Pollard work directly with every homeowner, business and property manager we serve, so you never deal with a revolving door of project managers.
18 years combined experience
of Florida roofing experience
License No.
Florida Roofing License
ROOFING SERVICE
Residential, commercial and multi-family roofing
24/7
24/7 emergency roofing
We Built Black Flag Roofing From the Ground Up
Before we started Black Flag Roofing, we spent years working in Florida roofing, and we saw the same gaps again and again: too little professionalism, too little education for customers, and too many people passed from one contact to the next. So we built our company from the ground up to fix that.
Today, Black Flag Roofing serves homeowners, commercial property owners, property managers and HOA communities across Lee and Collier Counties. The projects have grown, but one thing hasn't changed. When you call us, you work directly with the owners.
What Makes Black Flag Different From Larger Roofing Companies
We're equipped for large commercial and multi-family projects, and small enough that the owners still know every customer by name.
- You work directly with Chris or Spenser, from the first call through the final walkthrough.
- We explain what we find, so you understand your roof before you make any decisions.
- We take on small repairs, and we'll recommend one when it's all your roof needs.
- Property managers and portfolio owners get proactive maintenance, clear communication and one accountable contact.
- Roof inspections are free, and our 24/7 emergency line is the same number you call for everything else.
- Financing is available through Enhancify for homeowners who need it.
Our Mission Is Built Into Every Roof
Our mission is to protect and strengthen our Southwest Florida community with roofs you can count on.
That means showing up when we say we will, telling you the truth about your roof, and treating every customer like family. From the first call to the final shingle, it's the idea behind our brand line: Roofing Built on Service.
The Values Behind Every Job We Take On
Integrity
We recommend what your roof actually needs, even when that's a small repair instead of a new roof.
Craftsmanship
Every roof is built to the Florida Building Code, with an owner watching the details that matter.
Genuine Relationships
We'd rather be your roofer for decades than win one job and disappear.
Transparency
Itemized estimates, clear explanations and straight answers, so you always know what you're paying for.
Community Commitment
We coach, volunteer and raise our families in the communities we roof.
Meet the Owners Behind Black Flag Roofing
Chris Little
Co-Founder and President
A proud Texas transplant, Chris believes in doing things big—in business and in life. As Co-Founder of Black Flag Roofing, he helped build the company around integrity, craftsmanship, and genuine relationships. He works closely with homeowners, property managers, and commercial clients on projects throughout Southwest Florida.
Chris likes to joke that his true calling is the PGA Tour, though his golf game may suggest otherwise. When he’s not on a roof or the golf course, Chris is a football coach at Community School of Naples (CSN), where he enjoys helping young athletes develop discipline, teamwork, confidence, and perseverance both on and off the field.
For Chris, coaching and business share a lot of the same values: show up, do things the right way, take care of your team, and always keep working to get better.
Spenser Pollard
Co-Founder and CEO
Spenser Pollard is the Co-Founder and Owner of Black Flag Roofing and a Florida Certified Roofing Contractor with nearly a decade of experience in the roofing industry. Since making Southwest Florida home in 2018, he has built his career around relationships, accountability, and being actively involved in the community he serves.
At Black Flag, Spenser works directly with homeowners, property managers, associations, and commercial clients throughout Florida. His approach is simple: be accessible, educate the customer, and stand behind the work from the first conversation through completion.
Outside of roofing, Spenser is passionate about staying involved in the Southwest Florida community. He serves as an Act One Ambassador for Gulfshore Playhouse, supporting its mission to make theatre and the arts more accessible throughout the community. He’s also an avid golfer and can usually be talked into a round whenever his schedule allows.
Spenser lives locally with his wife, Ashley, and their son, Beckett. For him, Black Flag is more than a roofing company—it’s an opportunity to build something lasting in the same community where he and his family are putting down roots.
What Clients and Partners Say About Working With Us
Proud to Roof Our Own Corner of Florida
We're based in Naples and focus on Lee County and Collier County, from family homes in Fort Myers and Cape Coral to commercial properties and condo communities in Naples, Marco Island, Estero, Bonita Springs and Ave Maria. We also serve homeowners and property owners farther up the coast in Port Charlotte, Venice and Sarasota.
Answers to Common Questions About Black Flag Roofing
Who owns Black Flag Roofing?
Black Flag Roofing is owned by co-founders Chris Little, President, and Spenser Pollard, CEO. Both work directly with customers on every project.
Is Black Flag Roofing a local company?
Yes. Black Flag Roofing is locally owned and based in Naples, Florida, serving Lee and Collier Counties and surrounding Southwest Florida. Our owners live, coach and volunteer in the communities we serve.
Yes. Black Flag Roofing is a licensed Florida roofing contractor, License #[License Number].
You can verify our license with the Florida Department of Business and Professional Regulation.
Does Black Flag Roofing work with property managers and HOAs?
Yes. We work with property managers, portfolio owners and HOA and condo communities on roof replacements, repairs and yearly maintenance. See our HOA and condo roofing services.
Get to Know Us Over a Free Roof Inspection
The best way to see how we work is to let us take a look at your roof. We'll explain what we find, answer every question, and leave the decision with you.
or call (239) 449-3387.
