As the trend of interest in DevOps continues to rise significantly among industry practitioners, so does the need for software development organisations to understand how to successfully implement DevOps as they are faced with a wide range of choices, and very few guidelines on how to navigate through a plethora of valuable information.

An important question is the skillset required, and its role in the determination of suitable DevOps implementation strategy for organisations.

This study contributes to the above and provides insight by critically investigating the DevOps implementation of 14 organisations through interviews with practitioners who lead the transformation in these organisations. Interviews were transcribed, coded and analysed by a method informed by Grounded Theory.

We identified six strategies used by organisations to implement DevOps, which we named Platform, Greenfield Application, Monolith Decomposition, Process Improvement, Cultural Improvement, and Advocacy. Based on our analysis, we conclude the following: 1. A striking correlation exists between the skillset and the strategy adopted by organisations to implement DevOps. 2. The inclination of an organisation towards upskilling is relevant for the determination of appropriate DevOps implementation strategy.

From our research, we have come to believe that the choice of organisational DevOps implementation strategy should generally be based on a consideration of technologies, processes, culture, and skillsets as top-level concerns.