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.

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
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.
The great roofers who make up this company are competent, professional, trustworthy and honest. They never try to gouge anyone, but are very fair with pricing.
Thank you for years of excellent service! Randy is amazing and goes the extra mile when it comes to excellence in service!
Had a roofing job that needed to get relooked. Bruce sent a tech out that very morning. He found out what it was and made the repair in the rain! Waukegan Roofing stands behind their work! Would definitely recommend them to friends & family.
Very satisfied with the service that Josh at Waukegan Roofing provided. We had a small leak in our roof and for months, I tried to find it, but with no success. I called Waukegan Roofing to come out and take a look. Within 15 minutes, Josh not only found the small leak, but quickly caulked it and took care of the problem. What I also liked was that Josh could have reshingled the whole area at a much higher cost. But he felt that this was needed and that a good caulking job would seal the hole. I would recommend that you give Waukegan Roofing a call if you have any roofing needs.
I would recommend Waukegan Roofing to anyone! The quality, attitude and special attention to detail was appreciated. The cleanup was amazing! I would recommend Waukegan Roofing to anyone!
Your employees just finished 2 jobs here at our location: sealing leaks along a stretch of windows up on our roof and most recently repairs to and applying an aluminum colored coating to our corrugated metal east warehouse roof. I normally do not write to anyone about the workmanship of a job done here, but in this case I thought it’s something that I should do, especially in this case.The workmanship of the repairs was absolutely outstanding. The crew did a fabulous job of repairs & applying the aluminum colored coating to our corrugated metal east warehouse roof.All your workers were very professional in their conversations with me. Thanks very much for the jobs very well done.




