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John McCloskey has a diverse work experience that spans over 20 years. John started their career as a Senior IT Support Analyst at ICON Clinical Research, where they provided helpdesk and server support for multiple offices. John also played a role in creating the company's first intranet portal. After that, McCloskey joined The Second City as the Director of Technology, where they oversaw all technological needs across multiple locations in North America, including websites, desktops, servers, networking, and applications. John also developed database-driven web apps for internal staff. Currently, McCloskey is employed at Convergence Networks, serving as the Director of Business Services, North America. In this role, they are responsible for standardizing service efforts, overseeing the Inside Sales department, and implementing strategic efforts for operational excellence. John also serves as a vCIO and acts as a liaison between business executives and technical support teams, managing client networks and developing IT plans within budget constraints.

John McCloskey completed their Bachelor of Art degree in Computer Science and Economics from The University of the South in 2001. John then went on to earn their MBA in Finance from the Portland State University School of Business Administration between 2014 and 2017.