About Upside

Upside Roof Systems emerged in 2018 from the merger of two roofing companies owned by Mike Kennedy and Austin Railey – boasting over 40 years of combined industry experience. Our smooth transition to a larger company is rooted in an unwavering commitment to customer service.

As owners and operators, Mike and Austin handle estimates personally, avoiding the conventional commission-based sales model to build direct trust with customers. We prioritize quality over profit, utilizing top-tier materials and skilled roofers for durable and worry-free roofs.

Consistency defines our approach, whether it’s an 800-square-foot home or a 5,000-square-foot estate—each project receives meticulous attention. Every homeowner deserves to feel their project is crucial, and we uphold high standards in every job.

What distinguishes Upside? Our commitment, top-tier materials, consistency, and extensive experience. Engage with any Upside team member, and rest assured they are highly qualified for diagnoses and recommendations. From storm damage to insurance claims and energy efficiency, our experience is the bedrock of our business.

Mike Kennedy: Owner/ Operator


Mike has been in the roofing industry since 1997 working his way up from being the clean-up guy on a crew to owning his own company. He was born and raised in Louisville and attended Waggener high school and the University of Louisville (Exercise Science and Physiology). He enjoys road cycling and mountain biking and formerly spent several years racing competitively. In his down time, he can be found exploring the Parklands, conversing with friends at a local brewery, or relaxing at his Fisherville home with his wife and cats listening to music and enjoying the tranquility.

Austin Railey: Owner/ Operator

Austin has worked in roofing since 2004 in various capacities. As a native to the city, he was also a Louisville Metro firefighter for many years.  He attended Ballard high school, the University of Kentucky, and the University of Louisville (Exercise Science and Physiology). He enjoys skiing, running, and is active in his church. In his spare time, he works on home improvement projects and spends time with his wife, two daughters and their dog Maggie. 

Caitlin Barnes: Administrative Coordinator


Caitlin has been with Upside since early 2023. She is currently a Business Administration major at the University of Louisville with a marketing minor. She was born and raised in Louisville and attended Fairdale high school. She is an avid reader, often known to finish books in one sitting. Her hobbies include weekends on the water at her family’s lake house, exploring any and every local coffee shop, and hiking trails all over the area with her energetic pup Nala.


Beverly SweenyBeverly Sweeny
01:10 17 Apr 24
Fantastic job at our home! Highly recommend. They cleaned up and hauled away all materials. Personable. Estimate was thorough with receipt including photos of work completed.
Jennifer BJennifer B
19:51 15 Apr 24
Easy and seamless process!!
Matt MuellerMatt Mueller
19:49 15 Apr 24
Austin was great to work with! Scheduling and work performance were both very prompt and courteous. His expertise made a possibly troublesome diagnosis for an intermittent roof leak very quick and painless. Would highly recommend and use again!
Patrick CummingsPatrick Cummings
16:07 31 Mar 24
Austin and his crew were great. New roof shingles look good. They had the old shingles off and the new on in one day, a very long day for them. Came back the next day for some finishing touches and clean up that left the house and yard clean afterward. Could not be happier with how the work was done and look forward to the peace of mind the new roof will give me. Thanks.
Emily GriderEmily Grider
14:27 29 Mar 24
I highly recommend Upside Roof systems! Austin was very professional and easy to communicate with for all my questions or concerns. His team was amazing, I was so impressed with how fast and how hard they worked the day they came to replace my roof. They did a great job on cleaning up after they were completed. I was very happy with my experience with Upside Roof systems!
Shayla LohmanShayla Lohman
22:15 27 Mar 24
Austin was recommended by a close friend and did a fantastic job! He was so quick to come help us get quoted and fixed our roof problem in no time at all. Definitely recommend them for your next roof repair or replacement! Thanks again for all your work. 🙂
Edward RegulaEdward Regula
17:43 27 Mar 24
Outstanding service. Quick to respond to my inquiry and quick to complete the job.
Jean HullihanJean Hullihan
17:42 22 Mar 24
I needed a new roof but was reluctant for fear of being scammed. I got three referrals, all good, but I went with Upside Roof Systems because of their follow-up with pics and line item pricing of each thing that needed to be done within hours of looking at my roof. I knew what I would be getting and paying for. They respond quickly to any call/text and explained everything. The owner works with his seasoned crew. The roof looks great and I highly recommend Upside Roof Systems! Great job!!
Nancy McKinnisNancy McKinnis
23:12 20 Sep 23
Very professional & good work ethic!!
Mary SilvaMary Silva
13:03 17 Sep 23
Upside Roof Systems recently replaced my roof due to hail damage. Their work was excellent. The owner communicated with me throughout the process of inspection, insurance appraisal, scheduling and installation. Though it took a while to schedule the work (lots of homes had hail damage) they showed up on time and completed the job in less time than expected. The entire team was dedicated and professional. When finished, they cleaned up thoroughly and there was no damage at all to the lawn or landscaping. I wouldn’t hesitate to recommend them without reservation.
Beverly SmithBeverly Smith
18:50 08 Sep 23
So easy to work with and did an excellent job with both tearing off the old roof and putting the new one on! Could not tell they were here except we had a new roof! Thank you so much!
Brandon WhitakerBrandon Whitaker
21:56 21 Aug 23
Mike has now completed his second job for me. Him and his team replaced my roof a few years back and today he replaced the gutters on my home. I cannot recommend him and his crew enough to anyone seeking roofing or gutter work. They are punctual, Professional and very hard working people. You will not be disappointed in the quality of work provided.Mike takes the time to answer any questions and ensure you feel comfortable with any work performed. He provides various options on materials and makes sure that you are receiving the best for the money spent. I cannot thank him enough for the recommendation on the shingles he installed. They held up very well during this last round of storms.Mike and his crew certainly set the bar for roofing work and I would trust my Roofing needs with nobody else.
Tre PryorTre Pryor
15:16 18 Jul 23
Austin did a great job for us with a thorough inspection, fully repaired the issues and answered all of my questions. Highly recommend!
John PedroJohn Pedro
18:07 05 Jul 23
Really good work at a very affordable price. Austin is very personable and professional. He answered all our questions and made us feel comfortable with the process.
Denise SmithDenise Smith
17:13 21 May 23
We have had Upside Roof Systems install the roof on 2 separate homes & they also wrapped the overhang area with siding on our prior brick home. We highly recommend them due to their professionalism, value & communication.The day after the March 2023 windstorm Austin was out inspecting our roof & making the area where the shingles blew off waterproof until the new roof could be installed. We were blessed to just have shingles blown off & not any other major damage.Austin communicated with us in a timely manner the week our roof was scheduled, as the weather was an issue the week of our new roof install. I could not be happier!!I wish folks could see the roof up close because when I saw the pictures taken from the roof top, I commented to my husband, "That looks sooooo good!!" There were 2 vents that needed to be re-vented to code & that was taken care of as well!!Their professionalism is unmatched!! I trust them to be honest & let us know anything that needs to be corrected/added once the work on the roof was in process. They did a great job of cleaning up afterward as well!!When Upside Roof Systems is on the job, I know, without a shadow of a doubt, that the job will be completed to the highest standard!If you want a high quality roof installed by a company with integrity, hire Upside Roof Systems.
Loren CrawfordLoren Crawford
12:17 08 Apr 23
I could not be happier with my new roof! I was very anxious about the whole process, my poor old house has needed a new roof a long time. It's a complicated, high-pitched roof with many odd angles and a dreadfully configured gutter system. The house also sits midway up a steep hill- a real pain for roofers! Upside came in and overcame all difficulties, solving all sorts of problems. They were on time, positive, utterly professional. They reconfigured gutters that will alleviate wear and tear on the new roof and mitigate water in the basement issues. They even hooked up my rain barrel! I love how the roof and gutters look- just gorgeous. And when they left, the yard and sidewalks were much cleaner than when they came!
Joshua AustinJoshua Austin
04:21 30 Dec 20
These guys did a fantastic job. Austin inspected my roof and really won my trust through his thoughtful recommendations (ventilation, cricket vs no cricket, ect), attention to detail, and talking me through the best model shingle for my place. His crew showed up on time, did a very careful job, cleaned up perfectly, and left my ugly plants, drive way, and yard intact. I love the job they did, am happy with the pricing, and now heartily recommend Upside Roofing for anyone needing roofing work.

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Call Us Anytime: 502-305-4660