I totally agree, but OP's post doesn't seem to be of that type - it's not like he's chasing some nebulous tech buzzword ("Sprinkle in some blockchain!", "Be sur

I totally agree, but OP's post doesn't seem to be of that type - it's not like he's chasing some nebulous tech buzzword ("Sprinkle in some blockchain!", "Be sure to utilize AI!"), but he has a good idea of the specific pain points, at least in broad strokes. At the very least, similar to other comments about hiring a small group of senior freelancers, I think to start it makes sense to find a very good contract product manager who can map out, very explicitly, exactly what the pain points are and what a software solution would look like to fix them, stack ranked by "biggest bang for the buck" (i.e. most positive impact to revenue or reduced cost, divided by rough estimate of size of the fix). At that point the total investment would be very low, and then they can make the call of whether the risk of doing something not using COTS tools makes sense.