Imagine needing technology but not having the resources to spend on it. Imagine being so busy reacting to problems, you never have time to plan for the future. Imagine being so overwhelmed by new reporting regulations, you can barely get your staffers to update their passwords. Imagine trying to tackle these issues with a gaggle of outsourced workers, or a tiny, overworked and underqualified staff.

Most mid-market CIOs don’t have to strain their imaginations; these are the facts of their lives. Indeed, life in the mid-market is hard. Companies with annual revenue between $50 million and $1 billion have the same fundamental problems as enterprises in the Fortune 1000—resources, time management, compliance and staffing—but mid-market CIOs must address them in an entirely different manner than their wealthier counterparts. Indeed, recent data from CIO’s "The State of the CIO 2006" survey found that technology leaders in small and midsize companies are far more hands-on than their counterparts at larger firms. At the same time, while their brethren at larger companies usually report straight to the top, IT leaders at smaller companies often report to second-tier managers, making communication even more critical.

"Mid-market CIOs are always fighting fires," says Laurie McCabe, vice president of the small and midsize business solutions group at Access Markets International Partners, a research organization in New York. "In that environment it’s tough to think about the bigger picture, but the advantage they have is that if they can carve out the ability to look ahead, they can be more agile and flexible than a larger company."

As McCabe suggests, those CIOs who can deal deftly with the problems they face in the mid-market need to have something extra, a bit of wizardry. Larry Bonfante, Greg Seyk, Jim Taylor and Ken Meidell are four who lead by example, constantly innovating in a drive to compete. These technologists speak philosophically about the challenges they face, and recognize that like most small businesses, they have to work two or three times as hard as the big boys to succeed. Still, it seems none of them would have it any other way.

"Is being a CIO in the mid-market more challenging than being a CIO at a bigger firm? You bet it is," says Bonfante, CIO of the United States Tennis Association (USTA), the $220 million organization that runs the annual U.S. Open tennis tournament. "But nowhere else can you really feel like you’re making a difference every single day."