‘Hobby’ board games have been growing over the past twenty years. However, such games feature unique and complex mechanics that can represent a barrier of entry to welcoming new players, restricting the capability of the genre to continue its growth. ‘Bloodborne: The Board Game’ is one of these more complex hobby board games which could benefit from more understanding as to how technology can aid the welcoming of new players into the activity. While studies into companion applications to date have focussed on design models for companion applications in relation to existing hobby board gamers and experienced fans, there has been limited study into the ways that companion applications can be targeted towards new players and used as specifically rules teaching tools. Therefore, a web-based companion application has been developed for the hobby board game ‘Bloodborne: The Board Game’ to aid with reducing game complexity and helping to teach game rules. To evaluate the effectiveness of the proposed companion application, usability evaluations were performed to gather qualitative data regarding the experience of first-time users. Findings from analysis of the data showed that there should be a segregation of features between those designed for new players and those implemented for experienced players, with the automation of housekeeping tasks only adding to the complexity for new players, rather than reducing it. Furthermore, rules teaching methods have potential within step-by-step companion application tutorials, although these should be executed within a sandbox environment. In response to the findings, the conclusion presents the ‘Model for Companion Application Features According to Experience Level’, which can be used to aid in the design and development of companion applications for new players.