User Centred Design (UCD) and Agile Software Development (ASD) processes have been two extremely successful methods for software development in recent years. However, both have been repeatedly described as frequently putting contradictory demands on people working with the respective processes. The current research addresses this point by focussing on the crucial relationship between a User Experience (UX) designer and a software developer. In-depth interviews, an online survey, a contextual inquiry and a diary study are described from a sample of over 100 designers, developers and their stakeholders (managers) in a large media organisation exploring factors for success in Agile development cycles. The findings from the survey show that organisational separation is challenge for agile collaboration between the two roles and while designers and developers have similar levels of (moderately positive) satisfaction with Agile processes, there are differences between the two roles. While developers are happier with the wider teamwork but want more access to and close collaboration with designers, particularly in an environment set up for Agile practices, the designers’ concern was the quality of the wider teamwork. The respondent’s comments also identified that the two roles saw a close – and ideally co-located – cooperation as essential for improving communication, reducing inefficiencies, and avoiding bad products being released. These results reflected the findings from the in-depth interviews with stakeholders. In particular, it was perceived that co-located pairing helped understanding different role-dependent demands and skills, increased efficiency of prototyping and implementing changes, and enabling localised decision-making. However, organisational processes, the setup of work-environment, and managerial traditions meant that this close collaboration and localised decision-making was often not possible to maintain over extended periods. Despite this, the studies conducted between pairs of designers and developers, found that successful collaboration between designers and developers can be found in a complex organisational setting. From the analysis of the empirical studies, six contributing factors emerged that support this. These factors are 1) Close proximity, 2) Early and frequent communication, 3) Shared ideation and problem solving, 4) Crossover of knowledge and skills, 5) Co-creation and prototyping and 6) Making joint decisions. These factors are crucially determined and empowered by the support from the organisational setting and 3 teams where practitioners work. Specifically, by overcoming key challenges to enable integration between UCD and ASD and thus encouraging close collaboration between UX designers and software developers, these challenges are: 1) Organisational structure and team culture, 2) Location and environmental setup and 3) Decision-making. These challenges along with the six factors that enable successful Agile collaboration between designers and developers provide the main contributions of this research. These contributions can be applied within large complex organisations by adopting the suggested ‘Paired Collaboration Manifesto’ to improve the integration between UCD and ASD. Beyond this, more empirical studies can take place, further extending improvements to the collaborative practices between the design and development roles and their surrounding teams.