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Two questions drive just about every IT decision at the USO, according to VP of IT Craig Opel. Number one: "Are we meeting our customers' expectations?" And number two: "Are we using our donors' dollars wisely?"

Remove the word "donors" -- the USO is a nonprofit that generates much of its $350 million annual revenue from contributions -- and those questions serve as solid IT signposts for just about every small and midsize business (SMB). Opel's and his team's answers all point in the same general direction in 2013 and beyond: the cloud.

"Those two questions drive our investment strategy when it comes to moving to the cloud," Opel said in an interview. "That's the foundation upon which our strategy has been built."

The USO's customers aren't Joe and Jane Consumer or other businesses. The organization provides assistance programs, entertainment, and other services to U.S. military personnel and their families, maintaining more than 160 locations in 14 different countries. The far-flung nature of USO employees and customers alike is one driving force behind IT's cloud strategy.

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For some companies, a cloud initiative might be best summed up as: "Let's hope for the best." For the USO, it's a methodical, multi-year approach that aims to "build a bridge to the cloud" -- the USO's IT theme for 2013 -- by constructing a rock-solid business case each step of the way. First up in the new year: the USO just awarded a mobile device management (MDM) contract to AirWatch in order to stay on top of the glut of iPads, iPhones, Androids and other devices its 400 employees use every day. Opel said the MDM deployment will take one month because it will be delivered online -- instead of six months-plus of IT globetrotting to do installations at each of the USO's sites. If successful, it will become the next pillar in the bridge to a technology environment that exists largely online.

That bridge began in the USO's HR and corporate training departments, the organization's earliest cloud adopters. The human resources information system (HRIS), volunteer management system, and employee training are all already online, and with overwhelmingly positive results, according the Dr. Angela L. Kegler, the USO's corporate training manager. Kegler said the HR department achieved a 312% return on investment just six months after moving "USO University" -- the organization's employee on-boarding and training program -- online with Skillsoft. That helped make the case for the MDM budget, which in turn will lay the foundation for the next investment, provided results are similarly positive.

"This is a year of creating the analytical base -- that's why we call it a bridge," Opel said. "Building those cases out over the course of this year, we will use those as the foundation on which to get budget approval to execute in a lot of different areas."

Opel expects the USO's cloud transition to continue with "the low-hanging fruit" in 2013, pointing to the group's on-premises Microsoft Office licenses and Exchange email server as exhibits A and B. A move to Office 365 beginning in late 2013 is a likely next step, Opel said. Once it has a solid string of successes behind it, the USO will consider making bigger bets in mission-critical areas such as its Microsoft Dynamics-based CRM and financial systems.

"Those are the family jewels, so to speak," Opel said. "We want to build some experience, build some successes, take advantage of the low-hanging fruit, and then start to move into some of the more critical systems."

The ROI case is of course rooted in dollars and cents. Part of the USO's cloud shift is based on the basic thesis that moving online will ultimately save the organization money. But it doesn't end there. Beyond the bottom line, the USO expects the cloud to deliver performance upgrades and other improvements to the services it provides. Opel said IT relies heavily on "proxy metrics," such as analytics drawn from the "Tell USO" surveys of its large, external user base. That community included roughly 2 million military personnel and their family members that used USO technology services in the past year, according to Opel.

Some of the challenges the USO faces as its cloud strategy unfolds are typical among SMBs undergoing similar transitions. It will likely require retraining or new skill sets among the IT team, for example. One thing the cloud will not do, however, is hurt hiring; in fact, the USO's 12-person IT staff team will grow to 16 by the end of 2013.

Some obstacles are relatively unique to the USO's mission. A key one will be bandwidth -- Opel's team can't take reliable high-speed internet access for granted in some of the locations it supports. "What we can offer to our service members at Landstuhl [Regional Medical Center] or Ramstein Air Force Base would certainly be more robust than what we can offer our nine centers inside Afghanistan that only have satellite connectivity and limited bandwidth," Opel said. "Dealing with the fundamental technologies is one thing we have to overcome."

Security is top of mind, too, in part because USO employees handle personal information for active-duty service members. But security is less of a roadblock and more of an organizational mindset. Opel credits that to the USO's leadership and its recognition of IT as a strategic force rather than mere service provider. HR and training, the initial building block for the USO's cloud bridge, plays a key role here, too; employees receive significant training on the handling of customer information and other sensitive data.

"The cloud's for everybody but not for everything," Opel said. "We're just making sure we do it right and don't jeopardize that very personal, critical data of our constituents."

Join Cloud Connect for a free webcast with "Cloudonomics" author Joe Weinman. Cloudonomics is a new way to discuss the benefits of private clouds. Many have focused on the cost reduction possibilities while others have focused on business agility. However, private clouds can play a strategic role, as well. The Cloudonomics webcast happens Dec. 12. (Free registration required.)