A Roofing Team Built On Loyalty. Backed By Experience.
The Southwest Florida Roofing Company That
Sticks Around Because The Boss Does, Too
The Same Trusted Crew, Every Time
Have you ever wondered why it’s so hard to find a reliable roofing contractor in Southwest Florida? One of the biggest problems is the high turnover rate the industry faces.
When you need a roof replacement, it’s not always clear who you’re going to get – a newbie who doesn’t know much or a seasoned pro who’s been at it for years.
At Montgomery Winslow Roofing, we’re the exception to the rule. We have one of the lowest turnover rates in the region.
What’s our secret?
It starts with good leadership and a deep sense of care. Our owner, John, isn’t a paper-pushing kind of guy. Instead, he actively leads our team on job sites and understands the true value of family.
And because of that, our crew members rarely ever decide to leave…
Our Roofing Contractor Turnover
Rate? Next To Zero. Seriously.
With turnover so high in the roofing industry, it’s incredibly rare to find a company with as much staffing stability as Montgomery Winslow Roofing. But when we hire, we’re meticulous in our processes.
We look for team members who will uphold our values and do the right thing for our customers. And, in turn, we treat them right.
This mutually beneficial relationship has led to long-term working relationships with several members of our crews. Two of our lead installers have been with us for more than 15 years.
In the odd instance when we do hire, it’s typically someone we know and trust returning to the fold – not someone sent from a staffing agency.
Our minimal turnover ensures you get the best of everything when it comes to your roof replacement or repair. It enables us to consistently deliver high-quality craftsmanship, accountability, and results with zero surprises.
Why Our Roofing Team Stays, And Why It Matters
A good roofing company isn’t determined simply by the dollar amount on the paychecks – it’s determined by how the employees are treated.
At Montgomery Winslow Roofing, John doesn’t just check in with every crew every day. He’s approachable and genuinely cares about his team. For him, family comes first, and that’s demonstrated in his day-to-day decisions.
John also understands that sometimes life just happens. With that understanding, he’s always as accommodating as possible with the team.
That respect and courtesy go a long way, building lasting relationships. And because they feel valued, that value is passed on to you through better workmanship and an outstanding experience.
Our Roofing Leadership Difference
When John took over Montgomery Winslow Roofing in 1990, he brought a strong set of values to the table, including honesty and integrity. These values inspire us every day to make the right decision, no matter how difficult it is.
His son, Brad, is now stepping into a leadership role and is following in John’s ethical footsteps. And every day on every single job site, you’ll see one of them.
They actively engage with our entire team daily and ensure we have what we need to replace your roof correctly. Unlike other roofing companies, they’re also available to speak to you directly.
This top-down approach sets a tone of trust, respect, and personal accountability.
What It All Means For Your Roof Replacement
When you choose the team at Montgomery Winslow Roofing, you get seasoned professionals, not new hires getting their feet wet at your home. Your job will also never be handed off and forgotten because there’s constant oversight and daily check-ins.
We’re a people-first company – in how we treat our customers and employees.
Fly-by-night contractors are all too common, making the consistency we offer rare and valuable.
If you need a roof replacement in Southwest Florida, choose the team you can count on for years to come – choose Montgomery Winslow Roofing. Contact us today for a free estimate.