First, get a senior person to lead the effort. They need to have experience hiring and managing developer teams. Ideally, it is NOT going to be someone with a l

First, get a senior person to lead the effort. They need to have experience hiring and managing developer teams. Ideally, it is NOT going to be someone with a lot of wizz-bang shiny tech on their CV. You need someone who wants to understand your business, and will focus on business value, and swallow the elephant one piece at a time. > Strategies for attracting and retaining tech talent in a non-tech industry This varies, but if you manager to hire and retain 200 employees, I'm guessing that you'll do alright. > Experiences transitioning from third-party to in-house software (success stories and cautionary tales). If you have a decent manager and someone who can make sound technical decisions, you'll do well. > Potential pitfalls we might not be considering. You seem to have good awareness of the danger areas. Devil is in the details. Figuring out how to slice the problem and building things piece by piece will be important. > Alternative solutions we should explore. In general, outsourcing companies are hit or miss, but if you find a good one, you will get many of the benefits without the downside of managing software dev in house. Having a more seasoned person supporting the lead engineer will help you avoid costly pitfalls. I'm being self-serving, but a fractional CTO working a few hours per week might bring the kinds of safety check that will make such an endeavor more successful.