Under the Roof: The Inspiring Journey of Jack the Roofer

In the bustling city of Denver, Jack Cottrell, owner of Jack the Roofer, is known for his compassion, integrity, and excellence in roofing. With over two decades of experience, Jack has turned roofing into more than just a job, crafting uplifting stories of redemption and resilience from ordinary construction projects.
Jack isn’t your typical tradesman. A jack of all trades, having worked in virtually every capacity of roofing, Jack has seen it all. It was the late ’90s when he first entered the trade, starting out as a humble installer and working his way up through the ranks. And in 2015, armed with years of experience and just enough capital to take a chance, he took a leap of faith and founded his own roofing company—Jack the Roofer.
Some might view roofing as a mundane and unexciting trade, but Jack sees it differently. To him, every roof is a canvas waiting to be transformed, every project an opportunity to make a positive impact in someone’s life. He understands the importance of communication and organization, and he makes sure to keep his clients informed and involved every step of the way.
Running a successful roofing business is no easy feat. Jack has faced his fair share of challenges, from managing a growing workload to finding the right balance between customer service and business growth. But through it all, he remains committed to his core values, never losing sight of what matters most—his clients.
On one project, Jack found himself assisting a widow who urgently needed a new roof. With her husband recently gone, she felt overwhelmed by the prospect of tackling it alone. Jack guided her through each phase of the process, not only providing top-notch workmanship but also taking the time to offer a sympathetic ear and assist with navigating the complexities of insurance negotiations. The widow placed her trust in Jack, and he rose to the occasion with unwavering dedication and compassion.
Jack’s empathy and generosity extends to his employees as well. One day, Jack received a call from a man who had hit rock bottom. With his last dollar spent and nowhere to call home, the man found himself in dire straits and in desperate need of employment. Jack recognized the man’s potential and offered him a job on the spot. Not content with just providing employment, Jack went the extra mile by arranging a short-term stay at a hotel and even providing him with a company truck to facilitate his commute and help him get back on his feet.
Under Jack’s mentorship, the man flourished, becoming a valued member of the team and earning the respect and admiration of his colleagues. Over time, he regained his confidence, eventually making the decision to move back home to be closer to his aging family. Inspired by his experiences working alongside Jack, he took the bold step of starting his own roofing company, determined to pay forward the kindness and support he had received. Witnessing the remarkable transformation in his employee’s life, Jack couldn’t help but feel a sense of pride and satisfaction, knowing that he had played a pivotal role in helping someone overcome adversity and achieve their dreams.
As Jack’s business has continued to grow, he has never lost sight of the values that have guided him from the very beginning—integrity, compassion, and a relentless commitment to excellence. And as he looks out over the rooftops of Denver, he knows that he is exactly where he is meant to be—making lives better, one roof at a time.
Congrats to Jack the Roofer for being a Top 3 Finalist in our 2024 Best of Mile High awards program. All winners can be found here.