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John Cullen has an extensive work history in various roles and industries. John started their career in 1993 as an Installation Technician at GFD Communications and worked there until 1999. John then joined Actavo as a Supervisor and held that position until 2006 when they transitioned to become a Partner at Comsecure. After four years, they returned to Actavo and took on the role of Field Manager from 2010 to 2013, followed by Operations Manager from 2013 to 2017. In 2018, they joined Obelisk as Operations Director and held that position until 2020, when they became the Managing Director for Ireland. Currently, they serve as the Chief Operating Officer at Obelisk.

John Cullen obtained a Bachelor of Business (Honours) in Management degree from the Institute of Technology, Carlow during the period of 2009 to 2013. Their field of study was Business Management and Operations. In 2014 to 2015, John attended Lean Sigma Systems, where they pursued a degree in Six Sigma Lean Management. John focused on Yellow/Green Belt Six Sigma during this time.