The biggest problem is that Product and/or Sales are looking for constant growth via constant new features. It is impossible to get them to truly understand tha

The biggest problem is that Product and/or Sales are looking for constant growth via constant new features. It is impossible to get them to truly understand that by meeting some arbitrary deadline that you've had to take shortcuts. To their mind, done is done and now we need the next Y so they get their Q3 bonus. The next problem is that too often the tech team wants to do a complete rewrite every 12 months because they want to use hindsight to remake last year's system/feature today. The issue is that in another 12 months this rewrite suffers from the same problem and now has several more things to consider. Some technical debt will always exist and I would argue always necessary. Perfect is the enemy of good enough and software that isn't live isn't adding value to the customers or company. My perspective for this was to treat some percentage of work each quarter to resolving technical debt but do this in an agile prioritized way. Just like always focusing on the feature that will add the most value to the next release, also pick the biggest manageable issue that will reduce the debt the most to the next release. In this way, you know certain technical debt will never disappear but you have a ranked list to always decide the things that are most urgent and correct them before the house falls down. If your team is large enough, it is also helpful to have a person or standing task to update and document this list with WAG options and costs. Of course, as in all things, ymmv.