The core reason most orgs are "flying blind" is that we still don't have a reliable metric for technical debt. Management only tracks shipped features and velocity because they are easy to measure. They completely ignore the hidden liability of a rushed, messy codebase until productivity eventually grinds to a halt. You can't measure the economics of a team if you ignore the balance sheet.

Time to ship, change failure, rework rates, mean time to resolve, code complexity, code churn, average age of dependencies - there's a ton of reliable metrics for technical debt, but they have to actually be looked at to do any good.

The problem is that technical debt is a more complex concept & thus requires more metrics to properly measure than a simple concept like velocity.