The consensus among experts in Apple enterprise integration is that the iPhone is coming
– so companies should prepare for it now rather than be surprised later.

Most people agree that Apple’s original iPhone and the new iPhone 3G are a boon to consumers. These smartphones set the bar ever higher for screen quality and user interfaces. The iPhone version of the Safari browser is very close to a desktop Web experience and the new App Store feature keeps life simple yet immensely accessible for its users.

But what happens when happy consumers start taking their iPhones to work at big companies? There will be some hiccups but most companies have at least a year to plan for it.

Murphy: VC has $100 million available for new business application ideas.

Apple’s official statement is that the iPhone and the enterprise play well together.  “iPhone 3G includes the new iPhone 2.0 software with both the iPhone SDK and key enterprise features such as support for Microsoft Exchange ActiveSync to provide over-the-air push e-mail, contact and calendar syncing as well as remote wipe and Cisco IPsec VPN for encrypted access to corporate networks. The iPhone SDK allows developers to create amazing applications that leverage the iPhone’s groundbreaking Multi-Touch user interface, animation technology, accelerometer and GPS technology on the world’s most advanced mobile platform,” the company said in the iPhone 3G’s press release.  Apple also published a 58-page iPhone and iPod Touch Enterprise Deployment Guide, covering topics such as virtual private networks, device configuration and security.

APPLICATION WRITING
Among the users who’ll find this helpful are the 1,400 members of MacEnterprise.org, a virtual user group formed in 2001.  The group is traditionally just an e-mail list, but currently is rebranding itself to focus more on collaboration through Webcasts and wikis, said co-chairman Lance Ogletree. “The big thing that we’ve been discussing among ourselves is the application developer community,” he said.  “I would think that the next six months would probably be more of a telling tale as to what some of these corporate entities will be writing applications for.”

By day, Ogletree’s title is Systems Administrator 2, for the University of Texas M.D. Anderson Cancer Center. He said the existing Apple-provided tools work well, at least based on a few weeks of testing.

“Our intent is to examine the SDK and speak to the departments to see if they show interest,” especially for database integration, he said.  “We’ve got anywhere from 2,500 – 3,000 Macs within the institution; that’s somewhere around 15-20% installed base here,” he said.  In addition to a hospital-wide migration to Microsoft servers, “We’re a fairly entrenched BlackBerry institution. We’ve got a group that’s looking at enabling Active Sync on the Exchange Server for people’s accounts, sort of a bring-your-own-phone approach for people who want to bring Windows Mobile devices or the iPhone,” he said.

Schneier: iPhone security isn’t any different from other mobiles.

However, other than basics such as e-mail and network access, there aren’t many iPhone versions of enterprise applications per se.  A few major players such as Oracle are porting IT executive dashboards to the iPhone, but for the most part it is an afterthought or lip service. 

In lieu of any mass business adoption, money is available to kick-start developers who have fresh ideas.  Kleiner Perkins Caufield & Byers, the trendsetting venture capitalists whose past client list reads like a technology industry hall of fame, this spring announced the iFund – an initial batch of $100 million just for iPhone applications.  The company already has 2,200 business plans, 15% of which are focused on enterprises.  So far only five companies are funded, with iControl (a home automation system) and Pelago (a location-based social networking tool called Whrrl) disclosed to the public.

“With low single-digit percentage points [of market share], Apple is driving behavior and consumption that we’ve never seen before.  This was before they even announced the SDK and what that was going to do to the developer environment,” said partner Matt Murphy.

He noted that most of the iPhone world’s enterprise applications so far are merely ports of existing applications from other phones.  Many companies treat the iPhone as just another device to support, albeit a unique one. 

CONSUMER WAVE
It’s on the consumer side where the applications are more creative and use iPhone features such as the accelerometer, Murphy said.  But he expects that to change soon.  “The big question right now is… when does it become a high enough priority for enterprise users and the CIO of the organization to decide that they’re really going to put some weight behind it?  A lot of that may initially come from the IT shops themselves,” he said.  “If consumers are here now in droves, we’re maybe about a year away from seeing the whole mobile wave hit the enterprise anywhere near where it’s hitting the consumer.”

When that happens, Kleiner Perkins expects to pump in more money beyond the initial iFund.  Apple itself does not have a financial stake in the iFund, but gives marketing and technical advice to member companies.  Murphy said the full nature of the Apple – Kleiner Perkins relationship is confidential, however, “There’s more than a loose agreement around what each side is going to bring to the table, how it’s going to work and what each side is going to deliver,” he noted.

RISK MANAGEMENT
No matter how interesting the application, security is another huge aspect of getting any technology product to be taken seriously in the enterprise.  The iPhone 3G eats alphabet soup for its security protocols, including Cisco Systems’ IPSec, L2TP over IPSec, PPTP, WPA2 Enterprise and 802.1X with authentication.

Bruce Schneier, a renowned cryptology expert and computer security author who currently serves as Chief Security Technology Officer at British Telecom, said nobody knows yet if the iPhone is truly secure or insecure compared to other mobile devices.  A year or two could transpire before the iPhone’s security features prove to be good, bad or indifferent, he said.  “It’s got a cool screen but there’s nothing special about it,” he said.  “Security isn’t the same as measuring speed.  The odds of there not being malware are zero.”

Frankl: The necessary middleware is already plentiful.

“This is the risk of having a computer in your pocket.  They’re becoming powerful general-purpose computers.    You’re doing a lot of things yet it’s in an easy-to-lose form and that’s risky.” So companies are just like people – every day involves making conscious compromises about risk, Schneier said.  Meanwhile, until some attack arises, “They ignore security.  That is how companies balance it.  It might not be how they should, but when security goes against coolness, coolness wins.”

From user groups to investments to security, the iPhone 3G and its new 2.0 software is getting a healthy dose of enterprise attention.  A group calling itself the Enterprise Desktop Alliance does not yet have any household names among its small membership, but board member Peter Frankl said Apple itself is supportive of its efforts to show enterprise that middleware layers do exist, serving as another material in the foundation that true business software can build on. 

His own company, LANrev, provides desktop client management software.  “Virtually every large company we speak to have some number of Macs,” from which iPhone users always follow, he said.  “I think it’s just a sign that Apple is inevitably moving in that direction.”