In this paper we explore the effect of organizational structures on firms’ ability to attract and retain strategic human capital, and how employees’ personalities might moderate this relationship. We created a dataset based on the LinkedIn profiles of 8500 American professionals in the video game industry, spanning over 350 companies and 34 years. This involved coding each individual’s employment history across different firms to form a multilevel firm-person dataset. Moreover, adapting methods from prior research, we inferred individuals’ personalities by analyzing characteristics of their LinkedIn profiles, and use information on the different job titles of employees within the same firm to estimate the steepness of its corporate hierarchy. Our results show that employees’ personalities cannot explain their choice for working in either flatly or steeply organized firm. However, we discovered that post joining a firm, more extroverted individuals and those lower in openness are more likely to leave their firms early, and that all personality types have a higher risk of turnover the steeper the hierarchies of the firms. Most interestingly, the positive effect of a more hierarchical organizational structure on turnover is particularly pronounced for highly conscientious people, but less so for individuals who score low on this trait.