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Jamie O'Connor has a long and varied work experience. In 1988, they began their career as a Traffic Manager at Earl Palmer Brown. In 1990, they became an Account Executive at Arnold Advertising. In 1993, they moved on to become an Account Executive at TBC. From 1996 to 2010, they held various roles at D.C. United (Major League Soccer), including VP of Marketing and VP of Marketing. In 2010, they became a Regional Sales Manager at TicketSocket.com. In 2009, they founded O'Connor Consultancy LLC. From 2010 to 2016, they held various roles at TicketSocket, including Regional Sales Manager, National Sales Manager, and Vice President of Sales Engineering. Since 2016, they have been the Vice President of Customer Success at TicketSocket.

Jamie O'Connor has a Bachelor of Arts degree in Communication Arts from Salisbury University - Perdue School of Business, which they obtained between 1982 and 1986. Jamie also has a Bachelor's degree in Communications Arts from Salisbury University, which they obtained during the same time period.