You've heard it all before. The CEO buys an iPhone, falls in love, and leans on IT to shift its stack of tasks to make work-enabling his new gadget IT Priority No. 1.

But as IT departments scramble to sync e-mail and slap together Web apps for Safari-based iPhone access, the question remains: Can Apple's ear-candy crush object draft off this executive effect to true enterprise mobile legitimacy, or are execs' iPhone fetishes jeopardizing the integrity of their company's mobile strategy?

[ For an in-depth review of the iPhone, see "iPhone: The $1,975 iPod" ]

Here we examine the iPhone ecosystem's evolving backdoor bid for enterprise, one that pits security concerns, vendor intentions, and gadget affinities against caution-minded enterprise IT.

Executive inroads to the enterprise
A midsize company providing inventory supply services to schools, government facilities, and other institutions across the United States was perfectly happy with its mobile Palm-based inventory software until the CEO and other high-level execs purchased their own iPhones.

"Suddenly, they were saying, 'Hey, this is really nice,' and reevaluating their whole handheld strategy," says Ben Gottlieb, president of Stand Alone, which provides business inventory software and consulting services to the aforementioned inventory supplier. "Then came the questions about where the Palm OS was headed and whether their inventory application could be iPhone-enabled."

Mark Russell, vice president of sales and marketing at U-Line, a Milwaukee-based manufacturer of under-counter icemakers and refrigerators, had an iPhone for fun and a Nokia E70 for work until he accidentally crushed the Nokia device in his mother-in-law's recliner. Instead of getting a new E70, he asked IT to sync his iPhone with the corporate Exchange server.

"Our IT guy was nervous at first, but when Visto added iPhone capability to its Visto Enterprise Server, he gave it a try," Russell says, referring to the mobile messaging service provider, Visto. U-Line was already using Visto to sync its smartphones with Exchange.

Russell is perfectly happy with his business iPhone and has no intention of repurchasing the Nokia or any other device. And according to Daniel Koshute, U-Line systems administrator, several other employees are ready to make the switch as well.

The above examples are not unique. Like the PDAs, USB storage devices, and Wi-Fi devices that came before it, the iPhone is pushing its way through the side door of today's enterprises, thanks to a sexy interface, a superior mobile browser, and executive pressure.

"Apple has definitely achieved its goal of making you smile every time you press a keystroke," says Ken Dulaney, an analyst at Gartner.