Chileshe is a member of the Chartered Institute of Bankers (CIB) and was the top student of the institute in Zambia in 1996 and 19th in the world that same year. Until March 2015, he was the Country Manager for Sports4Africa, an online betting firm based in Europe. Prior to that, Chileshe was the Business Analyst for G4S’s Cash Solutions and Systems Solutions businesses. He was the de facto Finance Director of the two businesses. Chileshe specialises in P&L and Balance Sheet management, financial and business analysis, corporate governance, bids and management reporting.