Some of this depends on what a "product manager" does. Someone needs to prioritize, define, and design the migration off of the Jabberwocky servers, which haven

Some of this depends on what a "product manager" does. Someone needs to prioritize, define, and design the migration off of the Jabberwocky servers, which haven't had an OS upgrade in ten years, but have their IPs hardcoded all over the code base. Maybe you have product managers tracking technical debt and strategic technical priorities, but that would be an exception rather than a commonplace thing. But, even in those problems, focusing on and managing one predefined solution is usually an antipattern. But when this category of problems is ignored (because it is green field development, often), the build phase blows up because you need to be neck deep in code or deployment on some client facing problem to discover these sorts of issues.