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Gregg Schildberger has a diverse work experience in communications, public affairs, planning, and fan service management. Gregg started their career as an Administrative Intern at the City Auditor's Office. Gregg then worked in webmaster and public relations roles at the Hankinson Community Development Corporation. In 2008, they became the Manager of Fan Service Representatives and Ushers at the Fargo-Moorhead RedHawks. Gregg then transitioned to roles in communications and public affairs at The City of Fargo, ultimately becoming the Director of Communications and Governmental Affairs. Additionally, they have experience in photography, design, and talent consulting through freelance work.

Gregg Schildberger attended the University of North Dakota from 2002 to 2006, where they obtained a B.S.P.A. degree in Public Administration, Political Science, and Organizational Behavior.