In this work we explore digital transformation in software development. A set of interviews were conducted among industry experts to identify and elucidate the drivers and trajectories of digital transformation within the software industry. Using the Gioia method for qualitative analysis and synthesis, two major trajectories were found: (1) automation increasingly impacts several key activities related to software development; and (2) the importance of software and digital products is increasing in sectors where the core product or service has not traditionally been software-intensive. The findings have implications for the future of work in the context of software business. First, software developers and operators are increasingly needed, and more heavily involved across industry sectors. Second, as the level of automation becomes higher, the roles of automated testing and governance are highlighted, meaning a significant portion of development time will be spent in creating and validating automated tests. Third and finally, the importance of digital skills will increase also in non-IT roles as digital elements infuse into traditionally physical goods and services.