Relationships. Passion. Commitment.
Waterloo Roofing & Services is built on the foundation of placing the utmost emphasis on it’s customer relationships. Relationships are our cornerstone. Roofing is our passion. Integrity is our commitment.
Our Mission
Deliver year-round comfort through reliable heating and cooling solutions, built to handle any season.
Our Vision
To be the most trusted name in climate control — keeping homes and businesses comfortable, efficient, and worry-free.
Our Goal
Make energy-efficient heating and cooling accessible, while reducing carbon footprints and monthly bills.
Meet the Waterloo Roofing Team
At the heart of our company is a team of dedicated professionals who bring expertise, passion, and integrity to every project.

Jack Dailey
Jack founded Waterloo Roofing & Services as he noticed a need for a high quality and customer focused contractor in the Austin market. Jack has been in the industry for over 7 years with a wide array of industry experience. Starting as a roofing laborer in summers during college, to working as a commercial roofing manufacturer’s sales representative, to working in sales for a large commercial roofing contractor, he has a well versed background in what makes a team and a business successful. He places the utmost importance on the customer and ensures he is available and listens to their needs.
Jack graduated from the University of Alabama. Outside of work, Jack enjoys playing golf, spending time with his wife and their dog, and being out on the lake.

Ben Winter
Ben Winter is an Owner at Waterloo Roofing & Services LLC, where he focuses on business development as well as growing and expanding the company’s dedication to its clients in Central, Texas. With 7 years of experience in the home building industry, Ben is passionate about not only keeping an excellent working relationship with his clients but always delivering a complete job.
With the experience he has in home building, he has always been committed to making the end user happy. He understands timelines, honestly, and commitment is everything in doing so.
Ben graduated with a degree in Liberal Arts here at the University of Texas in Austin. He has spent his entire life in the city of Austin. Outside of work, he enjoys golfing, swimming, and being with his friends and family.

Matthew Preston
Matthew Preston serves as a Sales and Project Management for Waterloo Roofing & Services LLC. A lifelong Austin resident, he and his wife are raising their two young sons in South Austin. With more than 15 years of experience in customer service across the logistics and transportation sectors, Matthew brings a strong foundation in personalized service and reliable client communication.
Matthew believes success is defined by a client’s satisfaction and their confidence in recommending Waterloo Roofing & Services to the people they care about.
Outside of work, Matthew enjoys spending time with friends and family, seeing live music, playing golf, and taking his two dogs to the Austin greenbelts.


