This thesis explores the challenges and potential of mass timber as a paradigm shifting technology for the building industry through the application of parametric modeling technology to the design of office buildings. By testing building configurations in three zoning envelopes—low-rise suburban, mid-rise urban, and high-rise urban—optimization strategies for mass timber office buildings were developed. Facades and floor slabs were identified as the primary contributors to building cost and environmental impacts and therefore the easiest targets for optimization. The primary method for optimizing facades is replacing curtain wall with solid cross laminated timber (CLT) walls, this method runs counter to developer driven standards of fully glazed facades making short term adoption of this strategy unlikely without major shifts in building developer and owner expectations. Slabs and floor systems can be optimized through the implementation of novel solutions that take advantage of composite action between glulam, CLT, and concrete elements. Additionally, zoning height incentives could be used to make timber construction competitive with steel and concrete systems despite increased floor-to-floor heights. Finally, future research opportunities and needs, both architectural and technical, are identified.