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Robert Wilkins has a diverse work experience spanning several decades. Robert has held various leadership roles in different companies. In 1984, they founded Zones Inc., a mail-order reseller of Macintosh computers, where they served as the Founder, CEO, and President. Robert also founded Mac's Place/Egghead in 1990, a mail-order reseller of Macintosh products, where they were the CEO and President. In 1995, they founded RadGames and served as the Founder until 2006. From 1995 to 2006, they also held executive positions at PC Connection Inc., including Executive Vice President and President of Merrimack Service. Wilkins created Action Items in 2015, an organization tool that enhances productivity. Robert founded Ziftr in 2008 and served as CEO until 2015, transitioning the company into ZiftrShop. Wilkins was the Founder of AirTank in 2008, a design, development, and marketing agency that focuses on digital sales improvement. From 2008 to 2018, they served as Chairman of the Board at VenMill Industries Inc. Since 2011, they have been the CEO of SoCleanUSA, initially serving part-time and later transitioning into a full-time role in 2018. Finally, Wilkins joined Cefaly Technology in 2019 as a Board Member.

Robert Wilkins attended Jackson Hole Ski Management College from 1980 to 1981, where they studied Resort Management. Robert then attended Bellevue College from 1981 to 1982, focusing on Business/Managerial Economics. No degree was mentioned for either institution.