Dynamic offices that encourage collaboration and improve real estate efficiency are proliferating in knowledge worker settings. Beyond cost savings, research to date has been inconclusive on the consequences for employees. The increasingly unstructured nature of these offices, both physically and psychologically, may operate differently based on individual differences in personality. By performing secondary research analyzing data from a case study, this paper investigates the moderating effects of Big Five personality traits on the effect of a flex office on workplace satisfaction, employee engagement, and interaction-based work experience. The present study analyzes survey data collected from one site of a U.S.-based research and consulting organization. A two-way analysis of variance (ANOVA) is used to compare survey responses at four months after a pilot group’s (n = 53, 55% female) transition to a flex office with a control group in a traditional cellular office (n = 65, 42% female). Drawing on perspectives from the Five Factor Model, personality-based self-regulation, and Person-Environment Fit, this paper hypothesizes that higher ratings in personality traits of Emotional Stability, Conscientiousness, Extraversion and Agreeableness will support positive outcomes for employees in the pilot versus the control. Results indicate that employees who rate highly in Conscientiousness and Agreeableness, independently, have better overall work experience in flex offices versus employees who rate moderately on these dimensions. Highly conscientious employees have significantly more awareness of their colleagues’ expertise and their departments’ activities in a flex office versus a traditional cellular office. Findings from this study can inform strategic innovation, change management, recruitment, real estate development, office design and future research in Organizational Behavior, Ergonomics, Self-regulation and Environmental Psychology.