As consultants, this session’s speakers regularly see both sides of the coin: on the one hand, they get to know the leading-edge technologies that have just become ready for the market. On the other hand, there are customers with conservative operation teams, legacy systems, and strict data security regulations. In this session, they share some learnings from their consulting gigs, what business domain thinking did to their customers, and why the DevOps mindset changed the team spirit. They explain the different approaches they used to iteratively modernize a big Java legacy system into multiple self-contained systems, the different levels of architectural decisions they made, the impact on a classic organization structure, and the critical points along the way.