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About Us
On a Mission to Build a Culture of Family
Giving Back to Our Neighbors
As a local Portland Metro resident, you know that the Willamette Valley is one of the most beautiful places on earth: both because of the stunning nature and the rich community focus. We’re firmly rooted in the Willamette Valley, and we’re proud to give back to our communities by donating to a number of local charitable foundations.
The Boss Exteriors Story
In 2018, Gabe Callaway and his wife Hanna started Boss Exteriors. Both Gabe and Hanna were born and raised right here in the Willamette Valley. Gabe brings a decade of experience in new construction, remodeling, and house flipping to the table from before starting Boss Exteriors.
The Callaway’s goal has always been to fill a need in the contracting industry by fostering authentic relationships, providing prompt and responsive service, and taking stress off of local homeowners’ plates. They know that when they treat people like family, neighborhoods and communities flourish.
Our Core Values
To ensure the best results possible, all of our interactions with our customers and with each other are guided by our three core values.
Genuine
Responsible
Dedicated
Want to Become a Boss?
We’re always looking for skilled team members to level up our service for local Oregon homeowners. If you’re a hardworking and authentic professional looking for a rewarding place to work, we’d love to hear from you. Check out our open positions and apply today!
Meet the Boss team
Gabe Callaway
Owner and Visionary
Hello there, I’m Gabe. I am the Owner and Visionary at Boss Exteriors. I grew up in Canby Oregon and now live in Damascus with my wife of 11 years and our 3 beautiful daughters. I enjoy endurance trail running, snowmobiling and mountain biking. Tillamook Old Fashioned Vanilla Ice cream topped with a banana is truly the best scoop out there.
Rylan Phillips
General Manager
Hello, I’m Rylan Phillips and I am the General Manager here at Boss Exteriors. I grew up in Beaverton and live with my wife Staci and 2 daughters in Sherwood Oregon. Trail running and outdoor activities are how I love to spend my free time, the thrill of exploring new trail systems is my favorite kind of adventure. I balance my healthy lifestyle with a deep love for peanut butter chocolate ice cream.
Greg Moulton
Sales Manager
Hello there! I’m Greg, and I am the Sales Manager here at Boss Exteriors. I’ve worked in the construction industry for the past 15 years and one thing I enjoy about this business is leading and encouraging those around me. My family is my world, and I love watching my 4 kids compete in their MANY sports activities. In what little free time I have left after that; I enjoy hunting, fishing and traveling the beautiful PNW. In my professional opinion, Double Chocolate Fudge Brownie Ice cream is the best and only way to go.
Christina Fell
Office Manager
Hi! I’m Christina, and I’ve worked in the construction industry for 24 years. I am the Office Manager here at Boss Exteriors and I really enjoy creating standardization within the company to increase organization and efficiency. I am married with 2 beautiful children, and love spending time with my family and friends in my free time. My favorite flavor of Ice Cream is Salted Carmel.
Eric Powell
Exteriors Specialist
Hi there, I’m Eric Powell and I’m your Exteriors Specialist at Boss Exteriors. I grew up in Silverton Oregon and reside in Molalla. My wife Holly and I have 6 kids and 5 grandkids. I love fishing and cooking in my free time and I never met a scoop of strawberry cheese cake ice cream I didn’t like! I have worked at Boss Exteriors since February 2021.
Derek Dellinger
Project Manager
Hello! I’m Derek and I’m a Project Manager with Boss Exteriors. I’ve worked in the construction industry for 16 years and thoroughly enjoy working with homeowners as they turn their visions into reality. I’m married to the love of my life Savannah, and together we have 2 active children whom we enjoy camping, hiking and fishing with! As far as ice cream flavor’s go…homemade is always better, but I do love a good scoop of pistachio!
Michael Wakefield
Project Manager
Hi there, I’m Michael and I’m the Project Manager at Boss Exteriors. I grew up in Mulino and now live in Molalla. I have had 3 years of Construction Experience and enjoy learning and growing here at Boss. When I’m not working I like hunting and fishing, we really live in such a beautiful state! I’m pretty laid back…I haven’t met an ice cream flavor I didn’t like yet!
Hanna Callaway
Brand Director
I’m Hanna, and I’m the Brand Director at Boss Exteriors. I grew up in Philomath Oregon and now live in Damascus Oregon where my husband Gabe and I raise our 3 beautiful daughters. I love writing and recording music, drinking coffee and traveling. If you bring me Chocolate or Coffee Ice cream, but make it Dairy Free I’ll be your new BFF.
An Coon
Marketing Coordinator
Hi! I’m An, and I’m the Marketing Coordinator at Boss. I am married and live in Beaverton with my husband and our beautiful daughter Lucy. I grew up in NE Portland and worked in my family’s bakery. Production and the service industry is in my blood, and I credit that to the hard work and example of my parents. Creating and fishing are two other hobbies I enjoy thoroughly. If I had to choose a scoop, I’d pick Coffee Ice Cream every time!
Karen O.
Boss did a stellar job on our roof. Showed up when they said. Timely detailed bid. Complete tear off and replace done in 2 days. Office was responsive and paying was easy.…
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Brian F.
BOSS Exteriors did a fantastic job replacing our roof and installing new gutters. To start with they performed the most extensive inspection of the roof against competing bids. The crew did an…
Cheryl W.
We were extremely happy with the residing job and the pergolas that you guys built for us. thank you for helping us have the nicest house on the block. We appreciate you…
Danny O.
Scott came by to evaluate our roof and I was extremely impressed by his thorough explanation of the options for our situation, his professional demeanor, and non pushy attitude. He showed us…
Jason H.
Wonderful and excellent service from the Boss team. They replaced our roof last year, and just completed painting our exterior. Couldn’t have asked for a better team to work with. HIGHLY recommend!!!
Mary O.
I had a wonderful experience with Boss Exteriors! I had just made an offer on a home and had it inspected. Boss Exteriors saved me from making a serious and costly mistake…
Robin B.
We had a problem with our gutters and we were recommended to Boss Exteriors. Eric Powell met me at my home, on a Saturday morning, on time. The project we needed completed…
Serving the Portland Metro
From the Mountains to the Coastline
Portland
Damascas
Beaverton
Happy Valley
Lake Oswego
Gresham
Clackamas
Boring
Eagle Creek
Gladstone
