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Jim Calabrese has extensive experience in the finance and operations field. Jim served as the Chief Financial Officer at Finalsite, a software technology business catering to schools. Prior to that, they worked as the Chief Financial & Operating Officer at NCR Corporation (formerly dba Netkey, Inc.), a venture-owned software technology business specializing in self-service kiosk and digital signage applications. Calabrese also held the role of Chief Financial Officer and Chief Operating Officer at Vertafore, a software technology business focusing on the insurance industry. Earlier in their career, they served as the VP Finance & Controller at AMS Services and Manager of Strategic Planning at Yankee Gas. Calabrese started their professional journey as a Senior Auditor at KPMG.

Jim Calabrese earned their Master of Business Administration (MBA) degree in Finance from Rensselaer at Work. Jim attended the institution from 1997 to 2002.