I've been working for a software development agency in the past and one of my clients back then was (a different) mid-sized logistics company :)
For us (including the client) the following approach worked great and I'd recommend to give it a try
* hire an agency (or freelancers) to work on (requirements, architecture, design, implementation) your special software - make sure the code is yours legally and you can bring it to another software shop or internal whenever you want
* you get bootstrapping important decisions done by someone with experience. because hiring the first employee for that task is hard and risky
* you can transition to in house from there, if you're happy with the solution or decide to stay at that agency longer - you're very flexible
* Having good and maintained software as a base, start hiring. Build your team and gradually take over development. You don't have to go in-house fully, just so much that it makes sense.
Back then we bootstrapped custom software for that logistics company and gradually migrated it over to their team - even helped them hiring a team in the first place. Over time we lost them as a client (because they happily worked on their software now) but got many more clients since they recommended us highly. So it's a win-win situation.
For us (including the client) the following approach worked great and I'd recommend to give it a try
* hire an agency (or freelancers) to work on (requirements, architecture, design, implementation) your special software - make sure the code is yours legally and you can bring it to another software shop or internal whenever you want * you get bootstrapping important decisions done by someone with experience. because hiring the first employee for that task is hard and risky * you can transition to in house from there, if you're happy with the solution or decide to stay at that agency longer - you're very flexible * Having good and maintained software as a base, start hiring. Build your team and gradually take over development. You don't have to go in-house fully, just so much that it makes sense.
Back then we bootstrapped custom software for that logistics company and gradually migrated it over to their team - even helped them hiring a team in the first place. Over time we lost them as a client (because they happily worked on their software now) but got many more clients since they recommended us highly. So it's a win-win situation.