From your post it seems you're not quite ready to leave. So trying to share your insights and raise awareness may be worth a shot. That is, if you can comfortably speak with upper management without being singled out.
If the company is profitable and the users are pleased with the product then from an upper management perspective there may not be anything wrong. Until the bottom line is impacted there may not be leverage for change. The key is to alert management to the state of the product and the course it's on.
Parallel development may be an option as the next release of the product would address the underlying issues. This is costly and upper management would have to understand why that's necessary.
The company is quite profitable though keep in mind that the majority of revenue comes in from more traditional consulting projects. My estimation is that the software arm accounts for only 10-15% of total revenue.
There are a few other things going on here that I haven't mentioned yet:
- We've already pulled one client from the brink of not renewing a contract by developing a much simpler, web based version of our main offering. IMO this should be the general direction of the product but some users would legitimately miss some features.
- Management is well aware that the software is problematic. I believe they've been resting on their laurels for a while due to monopoly position. Things are changing though; competitors are catching up.
- it bears repeating that users are not happy with the product at all, but they are forced to use it by our true customers: their bosses. Those higher-ups do recognize that without ROI, however, the investment is simply not worth it. Now, the actual value of the product itself is another thing entirely...
If the company is profitable and the users are pleased with the product then from an upper management perspective there may not be anything wrong. Until the bottom line is impacted there may not be leverage for change. The key is to alert management to the state of the product and the course it's on.
Parallel development may be an option as the next release of the product would address the underlying issues. This is costly and upper management would have to understand why that's necessary.