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Jay Orcholski has a diverse work experience spanning various industries. Jay started their career in 2004 as a Broadcast Negotiator at Campbell Mithun. From there, they worked at the Milwaukee Journal Sentinel as an Advertising Preprint Manager, where they managed clients and ensured deadlines were met. Jay also served as a Majors Coordinator, ordering ads and providing support to sales representatives. In 2010, Jay became an Account Executive at IP5280, a VoIP and data provider, before moving on to work as a Consultant at The Journal News for a brief period. In 2011, they joined MegaPath as a Sales Manager, where they built a successful sales team and achieved top sales performance. Jay then transitioned into the role of Enterprise Regional Account Manager. Currently, Jay is the National Account Manager at Serviam - Telecom and IT Vendor Management, a consulting group specializing in telecommunications and technology.

Jay Orcholski attended the University of Minnesota from 2000 to 2003, where they earned a Bachelor of Arts degree in Journalism with a specialization in Advertising.