This was purely because of the legacy stack and poor management. The boss wanted to scale but did not care about tech, so we just never made real improvements. Sure, a feature got implement at least a week. We saw revenue grow a ton. We never saw time to improve our stack.
Safe to say I felt like I was adding nothing to that company. They just didn't want to grow despite saying the opposite. I get that the shiniest framework will not improve the project, but there were some serious bottlenecks that just got shoved under the rug