They fail in the gaps. Between what a customer asked for and what they meant. Between what was scoped in the deal and what engineering can build this quarter. Between a prototype that worked on a call and something an enterprise team will actually run.
The hard part is rarely the API. It is getting customer requirements, commercial priorities, product constraints and engineering reality aligned quickly enough to ship.
Bailey Wildash works across those boundaries. Close enough to the code to design something that will hold, close enough to the commercial side to know what it has to be worth.