Henry Eckstein loves a challenge. In August 2000, the 53-year-old New Yorker swam the English Channel in 14 hours and 24 minutes. He\u2019s also completed the 28.5-mile swim around Manhattan not once but three times. Later this year, he plans to swim the 22 shark-infested miles from Southern California to Catalina Island. Eckstein brings the same drive and passion for swimming to his job as the CIO of York Claims Service, a 350-person New York City-based company that provides claims-handling and administrative services to insurance companies and self-insured businesses. What he loves most about his job is that his company is big enough to require sophisticated solutions but small enough to afford him a hands-on role as a technologist. As the company continues to expand?since he arrived in 1993, the IT department has grown from two to 12?he realizes he\u2019ll be moving from the nuts-and-bolts aspects of the job and devoting his time to leadership. Eckstein looks forward to that role, but he\u2019s enjoying his gadgets while he can. "I like having my hands in things, and it\u2019s hard to relinquish that," he says. "I just like designing software and building systems. It\u2019s the big guy\u2019s Tinkertoys."Eckstein\u2019s top priority is making York a paperless office by March 2003. This means creating a huge document-management system and converting all the company\u2019s papers to electronic images?a monumental task. "We\u2019re solving a tremendous problem the company\u2019s had for years," Eckstein says. "It\u2019s amazing how much you can spend on real estate for file cabinets." The project was originally slated for completion by the end of 2002, but in the wake of Sept. 11, Eckstein\u2019s attention was redirected to beef up disaster recovery. The project is now moving along as planned and should be completed by the revised March 2003 deadline, he says.Eckstein is now much more attentive to the quality of his backup systems and spends more time testing his facility. He constantly wrestles with how much protection he needs. "What keeps me up at night," he says, "is knowing how far we need to go to make sure all our ducks are in a row."