Under Gillespie’s leadership, KeyCorp evolved from a collection of local banks into a national multi-line provider of integrated financial services. Beginning his career at Cleveland's Society National Bank in 1968, Gillespie rose through the ranks to become Chairman and Chief Executive Officer of Society National Bank in 1985 and was named Chairman and Chief Executive Officer of Society Corp in 1987. He serves as the Chairman Emeritus of KeyCorp. He serves as a Member of Advisory Board at CapGen Capital Advisors. Gillespie is a former Chairman of the Financial Services Roundtable, Board Member of the American Bankers Association and served as President of the Federal Advisory Council. He is the Chairman and member of Board of Trustees of A United Way and he also serves on the Board of the Cleveland Museum of Art, Ohio Wesleyan University, and the Musical Arts Association.