Ken Kelly Buys Back His Family Company

Three years after retiring and selling Kelly Roofing, Ken Kelly is back after a financial crisis threatened the company’s future. He shares what brought him back, the lessons learned from private equity ownership and his plan to rebuild the company around its employees, customers and culture.

Just three years after retiring and selling the family business he operated for three decades, Kelly is back in the president's seat, determined to restore the company his family launched in the 1972.

Based in Naples, Kelly Roofing, grew into a perennial RC Top 100 List performer and one of Southwest Florida’s most recognizable roofing contractors. Published reports that the company was shutting down operations a few weeks ago after its bank accounts were frozen, left many around the industry in disbelief.

It also left many customers scrambling to recover deposits and complete unfinished projects, which Kelly pledges to fix.

The contractor underwent a significant ownership change in January 2025, when Kelly Roofing and Integrity Roofing & Gutters announced a merger backed by private equity firm Monument MicroCap Partners.

Kelly said the journey back began with an emotional phone call from employees who feared they were about to lose their jobs. While enjoying retirement, he learned the business was on the brink of shutting down. Within days, he met with the team, assessed the situation, negotiated with the bank and completed the purchase of Kelly Roofing in less than a week.

"I couldn't let the employees or customers down," Kelly explained during this Best of Success podcast with Roofing Contractor’s Art Aisner and Jill Bloom. "This isn't about a paycheck. It's about doing the right thing."

For Kelly, the priorities were clear. First came protecting employees whose experience and dedication helped build the company's reputation. Next came honoring commitments to customers, followed by maintaining trusted relationships with suppliers and preserving the Kelly Roofing legacy.

Although the company had experienced challenges following several acquisitions, Kelly believes returning to a single-brand focus and restoring the culture that made the company successful will position it for long-term stability. He plans to simplify operations, eliminate unnecessary management layers and return to the leadership principles that guided the company for decades, including Entrepreneurial Operating System (EOS) practices and an "I intend to" leadership philosophy that empowers employees to make decisions while fostering accountability.

Kelly was also candid about the lessons learned from private equity ownership. While he emphasized that private equity can provide an excellent exit strategy for many contractors, he encouraged business owners to fully understand the emotional and operational realities that come after a sale.

One of the biggest lessons, he said, is the importance of founder mentality.

"When the founder leaves, sometimes the soul of the organization leaves with it," Kelly said, noting that leadership, culture and customer commitment often cannot be easily replaced.

Looking ahead, Kelly is optimistic. He expects the company to return to positive financial performance within months before eventually exploring employee ownership opportunities through an ESOP. Rather than pursuing rapid expansion or storm-driven growth, his vision centers on steady, sustainable success built on customer service, operational discipline and a strong company culture.

For an industry built on resilience, Kelly's return serves as a reminder that leadership often means stepping forward when people need it most. His comeback is more than a business transaction—it's a commitment to employees, customers and the values that built Kelly Roofing into one of the industry's most recognized names.