Context: Agile development methodology has been widely adopted by industry and the demand for experienced professionals in Agile-related roles is persistently high.Objectives: We focus on the learning path for a Scrum Master role in multicultural software companies and investigate the role in relation to team size, together with the learning process for a career path, and how companies monitor soft skills development.Method: We conducted our study in two phases, two qualitative surveys (interview studies) and performed a qualitative and quantitative data analysis of the results.Conclusions: Our results identified that the need for a Scrum Master (SM) depends on the size of the team, with our study indicating a six-member limit. There is no overall standardized process for soft skills learning or metrics to measure progress. Some companies measure soft skills based on feedback received from the client or from the team, and other companies are taking both types of feedback into consideration. Many learning initiatives, especially on soft skills for an SM role, were based on employees’ actions.