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Robert Cunningham has a diverse work experience in various roles and positions. Robert started their career at Uniflex/UFLINE in 1995 as a Production Artist, where they helped implement a computer network for the Art Department. Robert was later promoted to the role of Graphic Systems Administrator, responsible for setting up the company's computer network and workstations.

In 2001, Robert became the Production Manager at Uniflex/UFLINE, taking over a failed implementation of a new ERP system and successfully delivering an operational system on time. Robert also played a crucial role in keeping the company operational during a management crisis.

Robert then assumed the role of Director of Operations at Uniflex/UFLINE, where they oversaw all operations including the plant, warehouse/shipping, art, production, IT, and purchasing. Robert implemented a WMS on top of the ERP system and deployed digital flexo non-chemical plate systems, making Uniflex/UFLINE one of the first adopters in the country.

In 2006, Robert transitioned to the role of Vice President of Operations at Uniflex/UFLINE. During their tenure, the company was acquired, and they were responsible for the closure of production plants and warehouses. Robert also managed the transfer and production of work to a partner plant in Toronto, Canada.

In 2009, Robert was promoted to President of the Division and became a key member in the transition of a sale to a new equity partner. Robert also helped sell the Medical Division.

Most recently, Robert joined S. Walter Packaging in 2019 as the Chief Operating Officer. In this role, they oversee all purchasing, warehouse, customer service, printing, and graphic departments. Robert has implemented various restructuring and reporting structures, saving the company significant costs.

Robert Cunningham earned a Bachelor of Arts degree in Advertising from the School of Visual Arts from 1987 to 1989. Prior to that, they studied Graphic Design at Long Island University from 1985 to 1987. In addition to their formal education, they obtained certifications in advertising specialty information from The Advertising Specialty Institute, including a Bachelor of Advertising Specialty Information (BASI) certification in May 2014 and a Masters of Advertising Specialty Information (MASI) certification in January 2015.