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OUR TEAM

THE PEOPLE BEHIND THE PROMISE

Dedicated professionals. Elevated craftsmanship. A shared commitment to every homeowner's exterior—Central Oregon, start to finish.

OUR LEADERSHIP & EXPERTS

MEET THE TEAM

Years of combined experience. Specialized training. A crew that holds itself to a higher standard—on every roof, siding run, and window line across the High Desert.

Chase Caldwell, Owner

Chase Caldwell

Owner

Shayla Caldwell

Owner | Marketing & Community Relations

Shayla Caldwell

Owner | Marketing & Community Relations

  • 4 years supporting operations, branding, and customer experience for a family-owned roofing company.
  • Raised in Central Oregon and proud to still call this community home.
  • As a mom of three, stays involved through local sports, school activities, and supporting other small businesses in the area.
  • I love helping our community feel confident they're hiring an honest company they can trust.
  • When not working: spending time with family, photographing kids' sports, traveling, and enjoying the outdoors around Central Oregon.
Brian Dunn, Production Manager

Brian Dunn

Production Manager

Brian Dunn

Production Manager

  • 4 years of experience in roofing and 24 years of experience in construction.
  • USMC Veteran and Redmond local.
  • When not working: enjoys skiing, paddle boarding, and reading.
RJ Carroll, Sales Manager

RJ Carroll

Sales Manager

Austin Thomas, Estimator / Roof Inspector

Austin Thomas

Estimator / Roof Inspector

Austin Thomas

Estimator / Roof Inspector

  • 1 year of experience in the roofing industry.
  • Grew up in the Bend community.
  • Enjoys helping homeowners understand their roofing options and guiding them through the process of protecting their homes.
  • When not working: rock climbing, dirt biking, skiing, going to the gym, and spending time with friends and family.
Nolan Taylor, Estimator / Roof Inspector

Nolan Taylor

Estimator / Roof Inspector

Nolan Taylor

Estimator / Roof Inspector

  • 3 years of experience in construction and sales.
  • Born and raised in Bend and proud to serve the local community.
  • Enjoys working directly with homeowners and helping protect homes in the Bend community.
  • When not working: camping, rock climbing, and spending time outdoors.
Annie Winton, Office Administration

Annie Winton

Office Administration

Annie Winton

Office Administration

  • 5+ years in client experience.
  • The familial energy and kindness of the Homemasters team is unmatched!
  • Worked with several local businesses; volunteer for Hospice and Big Brothers Big Sisters in Central Oregon.
  • When not working: playing soccer, dancing/skating, and cold plunging.
Lizbeth Caldwell, Office Manager

Lizbeth Caldwell

Office Manager

Lizbeth Caldwell

Office Manager

  • 30+ years of experience in accounting, financial management, and HR.
  • Background includes more than a decade with Deloitte and other local tax/accounting firms.
  • Loves the pristine beauty of Central Oregon and loved raising her family in the shadows of Mt. Bachelor and the Cascade mountains.
  • Enjoys working with numbers and is thrilled when everything balances out.
  • When not working: loves to garden, making spaces beautiful, and exploring local restaurants.

Want to Work With Us?

Free, no-obligation estimates. The Homemasters team is ready to review the project—contact the office today.

CONTACT USCall (541) 527-7002