I think you've received lots of helpful feedback here. I've read quite some of it and can follow some thoughts. What I wonder is:
- Is anything broken after all? Yes, there are annoyances and risks, but in the greater schenem, everything seems to work. Is fixing really necessary or would you just feel better after that?
- What does the "aggressive roadmap" look like? Build another product? Double or triple the revenue from this product? I think this helps/defines how to handle the situation.
- Your job as middle level management (at least that's how I understand it, being in that position myself) is to shield your teams from direct hits with piles of shit, while getting them running to evade the stuff by themselves at some point. Seems like your team already did great things in building the product, now help them get better, one small step at a time. I think they can see the benefits in things like using Git but probably you need to help them make some room to learn it without fearing that upper level management thinks they are lazy and not doing anything...
- Leaving the company: Maybe that's a viable option, too. You can't save them all. And if you feel overwhelmed by the task and see no way forward, you should leave. That's not about being weak, it's about protecting yourself from an unmanagable task.
- Is anything broken after all? Yes, there are annoyances and risks, but in the greater schenem, everything seems to work. Is fixing really necessary or would you just feel better after that?
- What does the "aggressive roadmap" look like? Build another product? Double or triple the revenue from this product? I think this helps/defines how to handle the situation.
- Your job as middle level management (at least that's how I understand it, being in that position myself) is to shield your teams from direct hits with piles of shit, while getting them running to evade the stuff by themselves at some point. Seems like your team already did great things in building the product, now help them get better, one small step at a time. I think they can see the benefits in things like using Git but probably you need to help them make some room to learn it without fearing that upper level management thinks they are lazy and not doing anything...
- Leaving the company: Maybe that's a viable option, too. You can't save them all. And if you feel overwhelmed by the task and see no way forward, you should leave. That's not about being weak, it's about protecting yourself from an unmanagable task.