Studies have identified that employees use a variety of influence behaviours to achieve their objectives, with ingratiation being the most common of these. Researchers have called for investigations into the role dark personality plays in the display of ingratiation tactics. This study examines the influence of dark personality traits (i.e., Narcissism, Machiavellianism, Psychopathy and Sadism) on employee use of ingratiation tactics. Employees use ingratiation tactics to have better quality relationships with supervisor which can help them in achieving positive career outcomes. Social exchange theory posits that individuals build quality relationships with people who can prove beneficial to them. This research further explores the link between dark traits and career success outcomes via the mediating effect of ingratiation tactics and the quality of the relationship with supervisor (LMX). Ingratiation is considered a stress-inducing activity as it requires a lot of scheming and plotting, coupled with the risk of failure. However, individuals high in dark traits seek pleasure in the exploitation of others. The final aspect of this study explores the relationship between personality and psychological wellbeing through ingratiation and LMX. This study uses a quantitative survey design where data is collected from a heterogenous group of working professionals at two different points in time, three months apart. A serial mediation model is tested where employee dark personality traits are indirectly linked to career outcomes and psychological wellbeing through ingratiation and LMX. Narcissism and Machiavellianism were the only traits found to positively influence career success and wellbeing via mediators, ingratiation and LMX. Theoretical and practical implications of these findings are discussed.