Jon McCallus has extensive experience managing upscale eateries. After graduating from West Virginia University in 1995 he opened The Sunnyside Music Garden, a live music venue which offered a full service bar and cafe. After a successful two years, the establishment was sold so Jon could pursue a career in the music industry. Jon then opened another fine dining establishment, The Greystone where he served as front of the house manager and bar manager. In 2000, Jon moved to Chapel Hill and began work at the Acme Food and Beverage Co. where he was front of the house manager. In 2004, he accepted a position as bar manager at the Magnolia Grill in Durham, North Carolina. In 2008, Jon left the Magnolia Grill to start Cypress on the Hill.