Lots of good comments in this thread, but I think this is a critical one. It seems you've (OP) almost already decided, but you're unsure about details such as h

Lots of good comments in this thread, but I think this is a critical one. It seems you've (OP) almost already decided, but you're unsure about details such as how to retain software developers. Before you go into such details you need to be sure you want to make this move. This must be a strategic move, meaning a long term move where you're sure you're gaining a strategic competitive advantage through this being a core competence (in the academic/theoretical strategic sense). There are very few quick fixes in IT. Most projects are grossly underestimated - in particularly if you lack the competence in-house today (easily 10-100x). At it's core, it should be a decision that is not only about control over the software, it's about bringing the knowledge about the processes and technical complexities of doing your business in-house. You might think you know all about it, but most likely you don't (otherwise most IT projects wouldn't fail). The big cost in IT is specifying exactly how things should work (that's basically what coding is all about). If you're not a developer (and even most developers underestimate/don't fully understand this) it's highly likely you underestimate this part of it (otherwise it would be easy for you to code it yourself - again, how to code is not a big deal, it's specifying exactly how it should work). Software development is a lot about managing and documenting processes, aka knowledge, about your business. Otherwise I agree with lots of other comments. Make sure you and the rest of the business is sure and have enough budget/resources allocated for a long time forward. Bring in a CTO/leader with the experience/skills of doing something like this. Make sure that person has the mandate to do what's needed (hiring, culture, etc). Could be a good idea to do it step by step to test out (again, a good mindset is to see this as an investment in learning about how to do your business, using IT/automation). A hybrid approach could work (take over existing code, use another platform/ERP/system as a base) - all depends on the specifics of your business, how custom your business and processes really are, how core to your business they are, etc. Good luck!