Getting Business to Think Inside the Box.net

At 26 and with frizzy, out-of-control hair, Aaron Levie is not the typical khaki-and-blue-shirt-wearing enterprise programmer. And that’s fine by him. The college dropout came of age in the era of social networking and mobile applications and says he’s baffled by office programs that are hard to use, expensive, and inaccessible from his iPhone. When it comes to business software, he says, “the vast majority kind of sucks.”

Levie’s startup, Box.net, makes software that allows users to sync and share documents through the cloud. The goal is to make enterprise software simpler and more intuitive, and Levie plans to preach that message at Box’s first annual conference for some of its 60,000 customers, scheduled for Sept. 28. Investors are listening. The Palo Alto (Calif.) company has already raised $48 million this year and is now raising an additional $50 million in a round that values the company at more than $600 million, according to two people with knowledge of the deal. The war chest will help Box expand and go up against Microsoft and IBM, two heavyweights in the enterprise software market worth $245 billion globally, according to research firm Gartner.