Lindsay Crittendon
Chief Revenue Officer
Tailorbird

Lindsay Crittendon is Chief Revenue Officer at Tailorbird, an AI-powered platform streamlining CapEx planning for multifamily owners and operators. Tailorbird is the third AI company where Lindsay has led and scaled operations. She brings 15+ years of executive experience across proptech, insurtech, and health tech, including leadership roles at Hippo and Headspace. A strategic operator, Lindsay specializes in bringing category-defining products to market and driving growth through operational rigor. She is a founding member of Operators Guild, a startup advisor, and a University of Iowa alum based in the San Francisco Bay Area.