First off, as an occasional customer of logistics providers who sees so much crappy software held with duct tape and a wish, I completely agree that it is smart

First off, as an occasional customer of logistics providers who sees so much crappy software held with duct tape and a wish, I completely agree that it is smart to bring it in house. You need a solid team of at least two - a product person and a builder, preferably who have worked together before. Notice I didn't say CTO because some CTOs are admins rather than builders. Notice I also said product because you don't just need to build, you need to know what to build - and that might be part of the problem, if you're the one spec'ing the features and prioritizing bugs, you need someone to do this full time for you. I'd look for one of the two to start with and make it clear that you will expect them to build the team up as their very first responsibility. Most great engineers have product people who they can recommend and most great product people have software engineers they can recommend. I have come across people who operate very well with a specific offshore software dev team. If they can come in and bring their offshore connection, all the better (can be 1/2 as expensive as US). But in the formative stages, if you can afford it, I highly recommend an in-person team rather than off shoring, because it's a crapshoot that can be very expensive too if it doesn't work.