There is a lot to consider given your situation and you have lots of input here already. So, I would only add my 2 cents in the case you finally decide to bring

There is a lot to consider given your situation and you have lots of input here already. So, I would only add my 2 cents in the case you finally decide to bring the dev in-house: 1. Start the team from hiring *senior* talent. Prefer *pragmatic*, experienced, and reasonably "passionate" (about technology) people. 2. As soon as the software team starts to grow, hire at least one experienced product design / business analyst. Initially, someone experienced from the logistics department could work together with few software engineers and explain the business. At this point you need experienced software engineers who would carefully here you out, understand and internalize your needs, and translate this understanding into software. These same engineers would also need to expose you to the *just right* amount of technical details, for you to make the informed decisions about the product. I dare to say that everything else *does not matter* in a sense that you should trust this core team to make the right decisions in the area of software development. Eventually, as the overall complexity grows - product growth, team growth, etc. - you would need dedicated people to fill in this "bridge" role. Initial core team will get tired a bit, will need to focus on other things, so they'd need some help to structure the product. It is not easy, this role exists for a reason. It is overall less efficient this way (as in "output per person"), but necessary for further growth. --- *Most importantly of all*. Have you considered buying an out-of-the-box solution? Do they really-really not work? Replacing something that already exists... I never saw it go as expected.