ASP9: The Second Website Problem – Why DIY Sites Eventually Need Experts

Kelsey Gilbert-Kreiling is the Founder and CEO of Week of the Website, a Chicago-based agency that helps businesses launch strategic Squarespace websites through a unique one-week sprint process. With a background in fashion design, hospitality, and digital strategy, she has spent more than a decade helping organizations create websites that support growth, visibility, and customer engagement. In addition to leading Week of the Website, Kelsey is the creator of Eventually Ticketing, a Squarespace-native event ticketing platform. She is passionate about entrepreneurship, product development, AI-powered workflows, and building businesses that create space for both professional success and family life.