Executives learn from work experiences, advance through job changes, and move from companies to companies. Throughout this process, how do different work experiences relate to development of executive competencies and job mobility? In this study, we conducted a time sequence analysis to explore three primary questions: (1) What are the major paths of work experiences that lead up to senior executive positions? (2) How does an executive’s path of work experiences relate to post-GM job mobility? (3) How do executive competencies affect job mobility? Using sequence analysis on longitudinal data collected in 2001-2004 (Time 1) and 2019 (Time 2), we identified three distinctive paths of general manager (GM)’s work experiences in a Fortune 100 company across half a century from 1963 to 2019, namely stayer, internal mover, and external mover. Different paths of work experiences were associated with different levels of executive competencies measured at the transition point of taking on the GM position which led to future turnover and employer transitions. These findings highlight the sequential and temporal nature of work experiences in executive careers and also underscore the critical role of executives’ developmental paths on their future job mobility, therefore shedding theoretical and practical light on executive development and job mobility