Abstract: Synthetic polymers have permeated nearly every facet of modern life. From the ubiquity of polyolefins to recent advancements in 3-D printing, organic materials continue to shape the world around us. While tremendous accomplishments have been made with relatively few polymer families, the future requires the development of materials with increased control over structure to produce systems that can respond to programmed inputs, as well as the exploration of entirely new polymer compositions. Our group takes a chemistry-focused approach to address these challenges through the strategic application of organic methodologies to design new monomer families and reagents for precision polymer synthesis. This presentation will specifically highlight (1) the utility of enyne chemistry to impart degradability and expedite functionalization of metathesis-derived materials and (2) the development of a new class of living polymerization that is enabled by the unusual reactivity profiles of twisted amide molecules.