In his 30-year career with First Chicago, Vitale worked in commercial banking, real estate, private banking, foreign exchange, investment management, and corporate investments. Vitale served briefly as president and CEO of the Chicago Board of Trade (CBOT), where he oversaw the formulation of OneChicago, a futures exchange co-run by CBOT, Chicago Mercantile Exchange, and Chicago Board Options Exchange. In 2003, Vitale was asked by Mayor Richard Daley to become chief administrator of Chicago Public Schools (CPS), a job he accepted for one dollar per year.
His efforts to streamline CPS resulted in balanced budgets, incentives for school performance, and a much slimmer bureaucracy. Responsible for a $5 billion annual budget, Vitale reorganized the resource distribution process into a system of formulas, which gave administrators more time to concentrate on improving education and managing faculty. Vitale instituted a plan to decentralize CPS, giving 15 percent of its top performing schools greater autonomy in teaching students, training educators, and spending money. Replicating the flexibility that helped charter schools thrive, the plan was designed to allow the district to focus its resources on schools in crisis.