At a smaller company, definitely not. The focus changed at least yearly so planning that far out was fruitless. The one year plan was see what is making money and do more of that, keep the lights on, and try a couple quarter long experiments.

At the last big company, yes I was part of a multi year initiative. Part of that is probably mythical man month, we just couldn’t execute quickly. There were many teams and layers and dependencies that needed coordination, scheduling, headcount. Part was there’s enough legacy stuff that is core and can never break that every step had to be derisked a ton.