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Barry Rollins has an extensive work experience spanning over several industries. Barry is currently the Founder and Chief Executive Officer of Flare since November 2021. Prior to that, they founded tradefact in April 2016 and served as its Founder. Barry also held the role of Managing Director at Wineboxed.com from November 2015 to November 2017. Additionally, they worked as the Managing Director of WHA Direct BV's E-commerce division from December 2006 to March 2017. Barry also served as the Managing Director of LTR Co from August 2012 to November 2016. Barry Rollins has a background in entrepreneurship, having founded The Belfast Wine Festival in April 2011 and Domainnames.co.uk in November 2002, where they also served as the Chief Executive Officer until November 2007. Prior to their entrepreneurial ventures, they worked as a Commercial Pilot (Cargo) at Pilot from March 1999 to May 2003.

Barry Rollins attended the Royal School Armagh from 1991 to 1997. Barry later studied at cabair college of air training (Cranfield, Bedfordshire) from 1997 to 1999, where they earned a CPL (IR) frozen ATPL degree in the field of Aviation/Airway Management and Operations.