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Trip Alexander has a diverse and extensive work experience. Trip began their career as a Client Services representative at Impresse Corporation in 1998 and worked there until 2001. Trip then joined Radiant Systems as a Client Services Manager from 2001 to 2004. In 2004, Trip became the Director of the Western Region at GSP Marketing and held this position until 2006. Trip then worked as the Director of Business Development at Softix Pty Ltd from 2005 to 2006. From 2006 to 2009, Trip was the Development Manager at JYGY Inc. Currently, they are serving as the Director of Information Technology at Stamps.com, a position they have held since 2009. In this role, they are responsible for core product development, design, product management, quality control, customer implementation, and build and release management. Additionally, they support new business development and pre-sales activities.

Trip Alexander attended Georgia State University from 1990 to 1993, where they studied Economics.