Our team

The Family Behind Buddy’s Roofing

For more than 37 years, Buddy’s Roofing & Repairs, Inc. has grown through referrals, repeat customers, long-standing relationships, and a reputation for standing behind its work. What started with Buddy’s experience and determination has grown into a true family business, with Buddy, Crystal, Tiffany, and Carlos each contributing in different ways.

Through all that growth, the philosophy has remained simple: treat people fairly, communicate honestly, do quality work, and be there when your customers need you. That is what being family-owned means to us—and it is why we are proud to put our family name behind every roof we work on.

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Four Buddy's Roofing & Repairs roofers standing together outside an open industrial roofing shop

The crew

Who we are

Buddy Cheaves

Owner & President

Buddy Cheaves has spent virtually his entire working life in the roofing industry. He began roofing at just 16 years old in Tampa and went on to build Buddy’s Roofing & Repairs from the ground up. With more than 37 years of hands-on experience, Buddy brings an extraordinary depth of knowledge to every project, from residential repairs and reroofs to complex commercial roofing systems.
Although he is the owner of the company, Buddy has never been the type to manage from behind a desk. He remains personally involved in inspections, estimates, jobsite supervision, problem-solving, and making sure the work is completed the right way. His reputation has been built on experience, honesty, quality workmanship, and standing behind the work his name is on.

Crystal Gardner

Owner & Office Manager

Crystal is the heart of the day-to-day operations at Buddy’s Roofing & Repairs. From the first phone call through scheduling, proposals, permits, inspections, invoicing, documentation, and customer follow-up, Crystal works to make sure every customer knows what is happening and feels taken care of throughout the process.
As an owner of the family business, Crystal is passionate about providing the kind of personal service that can sometimes get lost in a larger company. She believes communication, honesty, and simply doing what you say you are going to do are just as important as the roof itself. For Crystal, customers are never just another job number—they are the people and businesses who have trusted her family to protect their property.

Jose Carlos Fernandez III

Project & Field Operations

Carlos represents the next generation of the Buddy’s Roofing family. Working alongside Buddy, he has gained hands-on experience with the many moving parts involved in roofing projects, from customer and project coordination to field operations and jobsite communication.
Carlos brings energy, problem-solving, and a strong work ethic to the team. Having learned from Buddy’s decades of experience while also bringing a younger generation’s perspective to the company, Carlos plays an important role in helping Buddy’s Roofing continue to grow while maintaining the workmanship and personal service the company was built on.

Tiffany Cheaves Fernandez

Administration & Project Support

Growing up in a family-owned roofing company means Tiffany has seen firsthand the dedication it takes to build a business and maintain a reputation over decades. Today, she contributes behind the scenes with administrative and project support, including permitting documentation, Notices of Commencement, product approvals, and other details that help keep roofing projects moving smoothly.
Tiffany brings organization, attention to detail, and a genuine family connection to the company. She and Carlos are also helping carry the family-business tradition into its next generation—something that means a great deal to Buddy and Crystal.

What that means at your door

The same standard on every visit

No subcontractors, no rotating faces, no commission on what they sell you.

Request service

Roofing work is the focus.
Repairs are part of the service.
Questions about your roof are welcome.
Work is discussed in plain language.
Service is available across Florida’s East & West Coasts

Reviews

Homeowners who count on us.

5 average, based on 126 Across multiple platforms

★★★★★

Buddy Roofing replaced roof and gutter. Both were completed with outstanding professionalism and efficiency.

bspider1 Dover · Google review

★★★★★

Amazing family owned company. Buddy and Crystal treated me like family and they didn’t even know me. I can’t say enough about this company and looking forward to working with them in the future.

Elijah Burroughs Dover · GMB-Deleted review

★★★★★

I can’t say enough for all Buddy’s do for our community. Not many will call you at 2am when you feel it’s the end of the world. 100% recommend and do appreciate how they go over above to help everyone. Very…