Background In this study, the association of work and demographic characteristics with different traffic offenses committed by food delivery riders in Greece was examined. Previous research has identified various factors related to risky driving however, there is a need for exploring the complex interrelationship of work-related factors underlying risky driving behavior. Materials and Methods A 2-items uestionnaire was used exploring delivery riders demographic characteristics, terms of employment, issues of concern during work and type of traffic offenses committed. In total, uestionnaires were analyzed using logistic regression in order to identify characteristics independently associated with serious traffic offenses, namely, red-light running and helmet non-use. Results The analysis showed that: (i) typical health and safety measures had no effect on serious traffic offenses, (ii) young age was related to both offenses however (iii) different sets of work conditions were associated with reports of red-light running (i.e. low work experience, use of personal vehicle for work, and payment by hour) and helmet non-use respectively (i.e. intense work pace, high tip income per day and low concern about vehicle condition). Conclusion The above findings provide evidence that serious traffic offenses are manifestations of underlying conflict experienced by the riders between safety and various performance criteria. Each one of the two offenses is related to different rider profiles aiming to satisfy different goals, namely, those mainly trying to maximize profit non-helmet users and those, mostly inexperienced ones, trying to cope with work pressure red light runners. Potential regulatory measures to alleviate risky practices are discussed.