Jamie Montag

Background

About Jamie Montag

For 15+ years, I've helped families in Kitchener-Waterloo and Cambridge improve how they live through ADUs, additions, and major renovations with Caliber Contracting. I also operate multiple Airbnb properties and commercial/residential rental properties, giving me hands-on experience with both the construction and property management sides of real estate.What I Do:Caliber Contracting: Specializing in ADUs (accessory dwelling units), major renovations, and additions throughout Waterloo Region. I navigate Ontario Building Code requirements and municipal processes to help families create additional living space, age-in-place, or maximize their property value.Property Portfolio: Active owner/operator of multiple Airbnb properties plus commercial and residential long-term rentals. This gives me daily experience with maintenance coordination, energy optimization, guest management, and the operational challenges property owners face.HomeWise AI (In Development): Based on years of managing properties and coordinating maintenance, I'm building a home management platform that helps homeowners stay on top of maintenance, understand their energy usage, and connect with trusted contractors. Think of it as preventive care for your largest investment.Why This Combination Works:My construction background helps me understand what actually needs maintenance and when. My property management experience shows me the real costs of reactive vs. proactive care. HomeWise AI brings these insights together in a way that serves everyday homeowners, property managers, and realtors.Current Focus:ADU projects and major renovations through Caliber ContractingOptimizing operations across my property portfolioDeveloping HomeWise AI based on real-world property management needsHelping Waterloo Region families maximize their homes' potentialConnect with me if you're exploring:ADU feasibility or major renovation projectsProperty investment or STR operationsHome maintenance optimizationPartnership opportunities in proptech or constructionServing: Kitchener • Waterloo • Cambridge • Guelph and surrounding areas