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John Rolander has a long history in the financial industry. John began their career in 1987 as a Market Maker at the Chicago Board Options Exchange (CBOE). In 1989, they joined Mesirow Financial as a Senior Vice President of Municipal Trading and Underwriting. John then moved to Fifth Third Securities in 2001, where they served as Managing Director and Head of Fixed Income Trading and Underwriting. In 2018, they joined Hilltop Securities Inc. as Head of Municipal Underwriting and Managing Director of Capital Markets. Most recently, in 2020, they co-founded Arcadia Infrastructure, LLC, where they serve as Chief Development Officer.

John Rolander attended the University of Iowa from 1982 to 1985.