Robert Boles

President of Winston Starts

Bob is the President of Winston Starts.  Winston Starts’ mission is to help drive future economic health of Winston-Salem, the Triad, and North Carolina through entrepreneurship, by providing intense, inspiring, and duration-appropriate support for startups with nationally scalable business models. Bob is also Chairman of the Board of Healthy Bytes, a start up nutritional counseling company that connects expert dietitians to providers, employers and patients. Bob is an accomplished operational executive, with solid track record of growing technology services and technology enabled businesses, with global management experience in Europe and Asia Pacific. Bob was CEO of Hostway, a $70M Cloud and Data Center services company; Senior Vice President of $750M, IT Infrastructure Services division at Cognizant Technology Solutions; Chief Operating Officer at Pegasus Solutions, a $200M global technology and business process services company for the Hospitality industry; President of AimNet Solutions a $30M Mid-Market focused IT professional and managed services company; and started his career with 18 years at IBM in several leadership roles in Sales and Marketing.  He has successfully raised private equity capital funding and completed Merger and Acquisitions from both a buy and sell perspective.  Bob graduated from the University of Scranton and currently lives in Winston Salem, NC.