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Dennis Wilson has a diverse work experience spanning over two decades. Dennis started their career in the food industry, working as a Lead Line Cook and Certified Corporate Trainer at The Capital Grille from 1999 to 2003. Dennis then moved on to Providence Prime as a Sous Chef for a brief period in 2004. In 2005, Dennis joined Vail Marriot Resort as a Server and later transitioned to 22 Bowens Wine Bar and Grill in 2006, where they also served as a Server. From 2006 to 2011, Dennis worked as a Server at Ruth's Chris Steak House.

In 2008, Dennis made a career shift to logistics management and joined Provant Health Solutions as a Logistics Manager. In this role, they managed a team and oversaw the delivery of hardware and products to clients and employees in the field. Their responsibilities included purchasing, vendor management and negotiation, nationwide shipping, equipment repair and maintenance, inventory management, and working with the product development team to customize programs for clients. Dennis utilized various software tools such as Microsoft Excel, Microsoft Dynamics GP, FedEx Shipmanager, and WebEx. Dennis remained with Provant Health Solutions until 2012.

Since 2012, Dennis has been working at Envision Technology Advisors. Dennis initially started as a Logistics Coordinator and later became a Solutions Engineer in 2014. Unfortunately, the end dates for these roles are not provided.

Dennis Wilson attended Johnson & Wales University from 1998 to 2000, where they pursued an Associate of Applied Science degree in Culinary Arts.