Research can help improve the lives of employees by revealing ways in which technology can be leveraged to progress innovative, time and cost-effective ways to promote their wellbeing. However, even with the trends of building “positive organizations” and promoting employees’ wellbeing using the latest technologies in today’s best companies worldwide, there has been a lack of rigorous research to provide solid evidence for these decisions. In this review, we present a call for future research to integrate and test technologically facilitated positive psychology interventions with gamification elements to better understand how to minimize harm and promote user benefits. We review the current online positive psychology intervention research, which we argue provides a critical guide for the development of future wellbeing technology. We also explore how gamification shows promise for promoting the benefits of positive psychology interventions (e.g., user enjoyment, autonomous motivation), as well as areas where gamification can pose a threat to wellbeing. There may be a fine line between harmful and helpful wellbeing solutions in our connected and technologically driven world of work; research now needs to uncover where to draw that line.