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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.
Krista Hendrickson
Controller
Hi! I’m Krista, and I’ve been working in the industry for 18 years. I have two grown boys, and we love to travel together! What I love most about Boss Exteriors is being part of a great team and seeing everyone work together.
In my free time, I love playing pickleball, hiking, and spending time with my friends.
Christina Rumble
Sales Coordinator
Hi! I’m Christina, and I’m the Sales Coordinator here at Boss Exteriors. When you call our office, I’m the one you’ll be chatting with!
I’ve worked in the construction industry for 25 years now. I really enjoy helping customers and figuring out solutions to problems. I also love being part of a supportive team where leadership encourages growth, and the company has a strong, family-like culture.”
I’m married, have 3 awesome kids, and 2 fabulous cats! When I’m not at work, I love to travel with my family, cheer on the Seahawks, and cozy up with a good book.
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 two beautiful daughters. 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. Being creative and the outdoors are two other hobbies I enjoy thoroughly. If I had to choose a scoop, I’d pick Coffee Ice Cream every time!
Ryan Ball
Carpentry Foreman
Hello, I’m Ryan and I’ve worked in the construction industry for 9 years. I’m a carpentry foreman for Boss Exteriors and I love working with a team of professionals that are constantly problem solving and improving in their craft. One of the most rewarding aspects of my role is setting my team up for success and collaborating to see a project through to completion. There’s a great sense of accomplishment in seeing the results of our hard work at the end of the day.
Four years into our marriage, my wife and I are embracing the joy of raising our beautiful daughter together. In my free time, I enjoy fishing, and spend most of my time with close friends/family. If I had to choose an ice cream flavor, a scoop of Umpqua Chocolate Peanut Butter would be my go to!
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
