This sounds fixable, but you absolutely must create some space to fix the problems. Don't even think about #3 -- it's not doable, and it sounds like the problem

This sounds fixable, but you absolutely must create some space to fix the problems. Don't even think about #3 -- it's not doable, and it sounds like the problem isn't just software. Start with #2, pointing out that it's going to get impossible to add features, scale, fix bugs, ... until the code and its environment improves. Read Joel Spolsky's famous list of 12 things that a software company must do (http://www.joelonsoftware.com/articles/fog0000000043.html http://www.joelonsoftware.com/articles/fog0000000043.html). If you aren't doing at least 9-10 of these, (and it sounds like you don't), you have to fix that. Or your company will die. Your CTO may say that he'll fix things as you recommend, and then do nothing. If that happens, then go to the CEO, and explain why these things have to happen. If he says the right things and then does nothing, your company will die. This will all take 6 months to play out, at least. If after 6 months nothing has changed, you might want to consider your options. But hopefully your CTO listens and really does something. If hiring is a top priority, you could point out that the horrendous code and environment will make it difficult to hire good people. Also, that fixing things is likely to reduce headcount requirements. Don't make your case in terms that make sense to you -- make your case in terms that make sense to your CTO and CEO.