As a product succeeds and establishes lockin, management may decide that devoting resources to improving the product's design has less relative ROI than devoting those resources to targeting new users who are not locked in. Those new users may be in an adjacent market that needs new features, which is typical when a product started in an intentionally narrow niche. New features crowd out the designs for old market users -- it's hard to stuff 10lb of shit in a 5lb bag -- and as the senior PMs & designers move to the new growth areas, more junior ones sub in to the old ones, and struggle even more.
It takes a LOT of design & product discipline & effort to avoid this. I think that's generally a disaster for consumer products, but in enterprise, which often pays for everyone else, the issue is much less clear, and especially on time scales that matter to individual employees. I'm always impressed when companies escape these kind of disincentive structures!