Steve's advice is sound in some situations but one factor not mentioned by him is the stability of the current platform. Are customers affected by bugs, poorly thought out process flow, etc.? Rewriting simply to add new features may be a losing proposition. But, rewriting because the current code base is so poorly thought out that it affects customers...now we MAY have good justification.
Also, the following struck me as odd, "Our CEO doesn’t have a technology background, but he’s frustrated he can’t get the new features and platforms he wants (Facebook, iPhone and Android, etc.)" Not knowing the situation better, I'm a little leery that the CEO is driving the new features when a product manager or someone closer to the customer base might be in a better position to determine what's needed. Perhaps in this company the CEO is close enough to the customer base, but I can't tell from the post.
Also, the following struck me as odd, "Our CEO doesn’t have a technology background, but he’s frustrated he can’t get the new features and platforms he wants (Facebook, iPhone and Android, etc.)" Not knowing the situation better, I'm a little leery that the CEO is driving the new features when a product manager or someone closer to the customer base might be in a better position to determine what's needed. Perhaps in this company the CEO is close enough to the customer base, but I can't tell from the post.