It's simple really: just use the stock market's herd mentality against it. Pick a large company that is information dependent and whose shares have shown significant volatility over the last few months. Then hack its systems, short the share, cause their systems to fail in publically embarrassing ways, and buy the shares you need at a significant discount.
The volatility will make it hard for the regulators to nail you and you can make money first on the price fall, and then on the inevitable rebound - think of it as a criminal win win.
United Airlines, for example, meets the target selection criteria, collapsed down to about $35 when its planes sat on the tarmac on June 18th, and recovered to its short term $39+ average by Thursday.
Notice, please, that I'm not saying this was done to United - I have no information about what happened there; I mention this example just to show how the market reacts to systems failures. What I am saying is that every eventus study of market reaction to IT news shows roughly the same pattern - and there are millions of dollars available to players willing to grab a little competitive advantage by creating the price movement pattern they're betting on.
So go for it: I know it can be more profitable than even WoW cheating, and my guess is that it's not a lot riskier - after all, do you really think that people are going to start getting fired for using junk technologies like wintel desktops and Cisco networking? Gimme a break; it's not gonna happen. I mean, sure it's every IT manager's job to protect the business, but as long as the idiots in charge keep authorising more of what plainly doesn't work there will always be so many innocent failures that no-one's going to notice you creating a few more just so you can make some real money.