When should a board of directors push for a CEO change? This case explores the experiences of the board of directors of a popular and successful lifestyle-brand start-up as it grapples with a public-relations crisis after a young female CEO makes serious missteps in a public forum. This case allows for a discussion of the role and responsibilities of a board of a start-up backed by venture capital (VC), when and how to remove a CEO, and the evolution of executive leadership as a company rapidly scales up and approaches a potential IPO. Through the case discussion, students take the perspective of the board of directors to come to a decision about whether (and how) to implement a CEO transition amid an unexpected crisis. A supplemental B case (UVA-S-0362) presents what the board chose to do next and provides an opportunity to discuss the longer-term leadership challenges that followed the initial crisis.