The men did an excellent job on the skylight removal and roof fill in. Thank you everyone for your assistance on this repair.

Meet Our President
Phil Diederich serves as President of Waukegan Roofing, bringing more than 25 years of hands-on industry experience and a long record of leadership to the role. A graduate of the NRCA Future Executive Institute, Phil holds GAF C.A.R.E. certifications and specialized expertise in air vent ventilation – credentials that reflect his commitment to technical excellence across every project. His influence extends beyond the company walls: Phil has served on the Board of Directors of the Chicago Roofing Contractors Association (CRCA) and co-chaired its Emerging Leaders Committee, helping shape the next generation of roofing professionals. At Waukegan Roofing, he leads with a clear focus on quality, accountability, and the long-term growth of both the company and the people who make it run.
Executive Vice President
Phil Diederich, Executive Vice President
With 25+ years of dedicated service at Waukegan Roofing, Phil boasts a wealth of certifications including GAF C.A.R.E. certifications, air vent ventilation expertise, and more. His industry experience extends to his previous tenure as a member of the Chicago Roofing Contractors Association (CRCA) Board of Directors and his role as the Co-Chair of the CRCA Emerging Leaders Committee. Additionally, Phil is a proud graduate of the NRCA Future Executive Institute.
Project Management
Project Manager
Joshua King, Project Manager
Josh is a seasoned roofer, and can navigate roofs of any height or steepness! With experience spanning roles from installer to estimator, he has progressed through the Roofing Apprenticeship Program to become a Journeyman Roofer. He is also certified in ventilation, GAF C.A.R.E., OSHA, asbestos handling, scaffold training, and Red Cross First Aid. He is dedicated to ongoing training and has completed several “hands-on” courses from industry-leading manufacturers.
Superintendent
Robert “Bob” Jefferies, Superintendent
Bob, a 5th generation roofer, grew up immersed in the roofing industry through his family’s commercial roofing company – Clayton Roofing (est. 1897). Starting as an apprentice with the Roofers’ Waterproofers’ Union Local 11, he eventually took a leadership role at Clayton Roofing to continue his family’s legacy. With the merger of Clayton Roofing and Waukegan Roofing, Bob brings decades of roofing and management experience to our team!
Certified in OSHA, CERTA Torch, asbestos handling, scaffolding, and Red Cross First Aid, Bob’s practical training complements his industry knowledge. His expertise enhances field production crew management, aligning perfectly with our company slogan – ” Roofs You Can Rely On.”
Quality Control & Safety Manager
Garen Rodriguez, Quality Control & Safety Manager
Garen dedicated 11 years to Underwriters Laboratories as a Fire Lab Lead Technician, specializing in residential sprinklers and roofing. In this capacity, he upheld rigorous standards for products bearing the prestigious “UL” logo. Following his tenure, Garen served for 6 years as a Field Inspector at Carlisle Syntec Systems, collaborating with roofers to ensure impeccable installations and conducting quality warranty inspections.
Why Waukegan
TESTIMONIAL
Our department is very grateful for the professional job your company completed here at the Waukegan Fire Department. Please express our great appreciation to your staff/personnel, and we look forward to working with Waukegan Roofing in the future.
Thank you for years of excellent service! Randy is amazing and goes the extra mile when it comes to excellence in service!
Please pass our thanks on to your team who were personable and, as far as I can tell, very thorough and careful in their work. It was greatly appreciated.
I was very impressed with the technical knowledge, professionalism, follow-up and communication. This is a first class outfit. Waukegan is top tier. They are a cut above the collective competition out there.
They put a new roof on my house 3 years before I bought the house. Then 2 years after I bought the house one of the plywood sheets lifted off a little creating a hole in the roof. A big problem. So I called and they had a crew out to fix it–no questions asked–within a few days. No charge, even though it was a few months out of warranty and even though I was not original customer. I was pleasantly surprised a company actually stands by their work like that–even five years later. They even inspected the whole roof and fixed another small issue I wasn’t even aware of.
What sold me on them is their honesty. We thought we were going to need a new roof. They could have sold us one, but the Waukegan Roofing representative who came over let us know that we didn’t need to replace the roof…we just needed a simple repair. We were impressed with their honesty, even though it resulted in a smaller job and less revenue. We have been sold ever since. The work they have done has been high quality too.
The immediate action taken by Waukegan Roofing once the problem was recognized speaks volumes about Waukegan Roofing and the willingness to take care of their customers. It is one thing to complete another construction project, but it is a completely different thing for companies to stand behind their work and make corrections when the customer needs you most.




