Redesigning a product is a complex process that can disrupt existing workflows and potentially lead to customer loss, but it is often necessary for advancing growth stages. Chameleon, initially a side project, underwent several iterations to improve user experience in onboarding, inspired by platforms like Squarespace. Early prototypes, developed with feedback from customers like Mesosphere and Amplitude, helped secure funding and refine the product towards a more user-friendly interface. The redesign efforts focused on creating a dynamic tool for in-app prompts, allowing real-time editing and previews without navigating away from the main application, which increased customer engagement. Despite the challenges of resetting the product’s polish and facing potential user churn, continuous customer interaction and qualitative research informed the development of new features, culminating in a powerful yet simple tool. The Chameleon team emphasizes the importance of early broad changes, maintaining customer relationships, and involving the entire team in the redesign process to achieve product differentiation and fulfill market needs.