My impression was that we'd squeezed all the blood we could out of the stone, yet the CEO wasn't going to accept "focus on other business problems" as an answer.
Eventually my pleas were heard and they consulted out a new platform. They didn't pick a platform that I wanted to administer, so I moved on. The fourth manager they hired after I left did not appear to have made any purchase on the problem the last time I talked to her.
I naively thought the problem was technology, but the real problem was the expectations of the CEO. There was nothing I could do about it, of course, so it worked out for the best.
A client one time told me in the past. At the time, I wanted to ask, "so, how badly are you treating them?"
This problem isn't unique to in house teams. It's hard to find and motivate competent people whether salaried or consulting.
Most companies attempt to tackle this problem in house, but without proper expertise, there is massive waste in hiring and poor execution. As a consultant, I’ve seen teams waste _years_ fumbling in this cycle, only for me to ship a product that immediately increases revenue in a fraction of the time. It generally only takes a few basic UI improvements and timing strategic automatic email tiggers.
Find a consultant that will make more from what you already have, and move on to your business problems. You don’t need to pivot into an internet company to be successful.