Schiesser's five months at iExchange gave him his only CEO experience. Afterward, Schiesser shifted into an executive position at a company that suffered one of the biggest meltdowns in history. He served as vice president of the emerging business group at Enron shortly before the company's 2001 collapse.
Schiesser relied on his college buddy for his next job. After leading a buyout of WellCare in 2002, Farha immediately hired Schiesser as the company's vice president of marketing and president of prescription drug sales. With Schiesser in charge, WellCare's Medicare business blossomed. The company, which had focused primarily on Medicaid in the past, rushed to capitalize on opportunities created by sweeping Medicare reforms. By September 2005, WellCare had surprised many by emerging as one of few companies approved to sell Medicare prescription drug plans on a nationwide basis. Schiesser cashed in on that success, selling $2 million worth of WellCare stock during the spring of 2006 alone. Shortly after those transactions, Schiesser found himself defending WellCare's Medicare program in testy exchanges before Congress. Just a month after that Congressional hearing, Schiesser abruptly stepped down from his post and shifted into a part-time advisory position -- paying a fraction of his old salary -- instead. In an attempt to explain the surprising move, Farha told the local St. Petersburg Times that Schiesser simply wished to spend some time in Spain with his wife and young children. However, in retrospect, WellCare itself looked hungry for change. Even as WellCare scaled back Schiesser's responsibilities in mid-2006, the company was already courting a powerful replacement. Gary Bailey, a longtime official at the Centers for Medicare and Medicaid Services, soon emerged as the new leader of WellCare's Medicare division. Before then, Bailey had overseen the very Medicare programs that were fueling WellCare's explosive growth. Notably, during Bailey's reign, CMS automatically assigned nearly half-a-million customers to WellCare's plans and transformed the company into a Medicare powerhouse in the process. Since mid-2006, Bailey has overseen that booming business himself. The following summer, Bailey even defended the business before Congress -- as Schiesser had done before him -- when it came under scrutiny yet again. "It is our company's ethic to do more than merely 'follow the rules,'" Bailey insisted at the time. "We have no tolerance for any unethical behavior." Apparently unconvinced, the government sent 200 agents out to raid WellCare's headquarters just a few months later.


