This study examines principals' job satisfaction in relation to their work intensification. Frederick Herzberg's two-factor theory was used to shed light on how motivating and maintenance factors affect principals' job satisfaction. Logistic multiple regressions were used in the analysis of survey data that were collected from 2,701 elementary and secondary school principal members of the Ontario Principals' Council in Ontario, Canada. Approximately 1,423 valid cases were used in data analysis. Results show that principals' work intensification affects their job satisfaction. As a result of work intensification, motivating factors, such as workplace challenge, recognition from the employer, and work demand; and maintenance factors such as external policy influence, organizational support, principals' relationships with teachers, superintendents, and unions are having a significant impact on principals' job satisfaction. These factors affect the extent to which they are able to contribute effectively to improving student achievement and school performance.