Duval County Public Schools finds itself at a crossroads with the impending departure of Superintendent Nikolai Vitti. Following significant improvements to public education since 2012, where does Duval go from here? How will the Duval County School Board go about appointing a successor? What are some of the key factors that make for a successful superintendent search, and what are the lessons learned from previous searches? This report reviews the background of the previous search, discusses considerations for today's context, and reviews research on what makes for a good match between school boards and superintendents. It concludes with recommendations to build on the progress Duval County has seen as a new leader is sought.