Annotating sport performances enables to quantitatively and qualitatively analyze them, and profile athletes to identify their strengths and weaknesses. We present the case study of the design and use of an annotation and analytical tool tailored to lead climbing analysis, developed with and for the French climbing federation. We used an iterative design cycle mostly fueled by virtual meetings with the federation trainer and analyst to identify requirements and implement essential features over time. We complemented these meetings with two workshops involving them, as well as French athletes competing at the international level, to identify the tool advantages and limitations. We contribute a list of insights based on the design process and feedback from stakeholders that inform the design of annotation and analytical tools for lead climbing and potentially other sports.