What Made This Roofer Different: Attention to Details That Others Missed

Yesterday, I told you about the roof we needed — and the months of bids, no-shows, and dead ends that followed. The right roofer came through an unexpected recommendation from my hairstylist: her friend April, a professional makeup artist who founded her own roofing company.

We Asked Santa for a New Roof — Instead, We Found a Roofer Unlike Any We’d Met Before

The first week of January, April Santiago with Bootstrap Roofing came by to look at our project. Of all the roofers who walked our roof, she spent the most time up there. She took a lot of pictures so I could see what she was seeing, and when she came back down, I finally learned why we had so many leaks over the years.

When the roof was installed in 2007, the roofers did not install air vents or “whirly birds.” Without proper ventilation, the attic got so hot that our shingles bubbled and the roofing nails popped. Those failures, she explained, led to one leak after another.

“We’ll give you a RizeRidge… your roof will look beautiful,” she told me.

I wasn’t sure what a RizeRidge was, but I knew I wanted one.

Once she explained the whole project, she stopped for questions. I’m sure she meant questions about my roof, but I wanted to know about her.

“April,” I asked, “how in God’s name did you go from professional make-up artist to roofer?”

At the age of 20, April earned her cosmetology license and worked as a professional makeup artist for international news, tv shows, commercials, film, special events, weddings, and freelance work. It was a career she loved and in which she was in demand.

That all came to a screeching halt in 2020 because of the Covid-19 pandemic. Cosmetology jobs disappeared.

“At 52, I had to recreate myself after having a successful career for 32 years,” she said.

During that time, she was dealing with her own home improvement headaches. One day, while shopping at Home Depot for plumbing supplies, she noticed the store was bustling with tradespeople who were still working, and it got her thinking.

“I brought it up to my family several times about getting into roofing and wanting to make a difference after having a few very bad experiences with roofers and contractors,” April said. “It wasn’t just the lack of workmanship but also the lack of communication and care after hiring their company. I wasn’t alone. My friends and neighbors had similar experiences.”

With help from her family and friends, April went to work for a roofing company so she could learn the business. She started Bootstrap Roofing in October 2020 and formed an LLC in 2023. The impetus to go out on her own came while volunteering at the National Women in Roofing booth at a local roofing convention. She met a fellow female roofer who had already been in the business for years.

“She shared all her contacts with me and pushed me to go out on my own,” April said.  “She gave me her roofers’ and insurance companies’ information, as well as always being available for any guidance. She’s been an incredible friend ever since.”

In 2024, April became an approved Owens Corning Preferred Contractor. She is also a member of the Better Business Bureau and the National Women in Roofing. She regularly attends classes with Owens Corning and GAF, as well as attending their academy in Colorado. 

At this point, I understood clearly why April spent more time on my roof than the other roofers. She knows roofing because she studied it. It was like seeing a specialist who could finally give you the right diagnosis.

“And just so I could have knowledge on the adjuster’s side of claims, I got my All Lines Adjusters License in 2024,” she said.

“There are three people who run Bootstrap Roofing,” she said. “Me, myself, and I. There are no salespeople and no pressure. We only work on one roof at a time, so I can give full attention to the homeowner’s project.”

We became her one roof on Jan. 21, when her crew arrived to start work. The first thing April did was set up a table and chairs so her crew could have a place to sit and eat, and then she brought donuts and coffee for them.

“I don’t like the way it looks to just have guys sitting in the yard eating lunch. I want to take care of my guys,” she said. “They should have a place where they can sit and eat. My crews are very patient with me because they know how detailed I am. I get on all our roofs to inspect the work to make sure they’re all ‘April’ approved.” 

It turns out that our bubbling shingles weren’t the only thing causing the leaks. Some sections of wood needed replacement because of rot, and in places, the wood was missing entirely because the previous crew did not make the repair.

As for the porch, where we’d been told that roll roofing was our only option, we now have shingles that make the roof and porch one. April pulled out the manual and learned how we could get shingles instead of roll roofing, and it would all be covered by the warranty. She read the manual!

When the crew was done, and everything was loaded back on their trucks, there was no construction debris left behind. They cleaned as they worked. The price tag came in under $9,000.

At the end of the day, I thought of my hairstylist Amy. She said April would give me a beautiful roof and that I’d love her. Amy was absolutely right on both counts.

“People ask how I chose two totally different careers. But they’re not,” she said. “There’s the artistry of roofing. Each roof is a complex composition of materials and techniques. While the process may seem chaotic, the result is a blend of functionality and aesthetic appeal.”

I could not have said it better myself.