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Gearldine Bailey has a diverse work experience spanning over two decades. Gearldine began their career as a Programmer at Teledyne Advanced Materials in 1995, where they developed and implemented programs for the Accounting & Purchasing system. From 1999 to 2002, Gearldine worked as a Senior Computer System Analyst at COLSA, where they performed data modeling and designed GUI screens. At Jacobs Technology from 2002 to 2008, they served as a Computer Programmer IV, supporting LOGSA ITSS WebLOG team and improving Army Readiness through enhanced equipment visibility and user interfaces. From 2008 to 2009, Gearldine worked as a Software Engineer at Teksystems, maintaining and developing interfaces for the Institutional Services Team at NASA. Gearldine then joined SAIC as a Senior Computer Scientist / Team Lead from 2009 to 2010, where they developed applications using PHP and served as a ColdFusion developer. Gearldine also has experience at Booz Allen Hamilton as a Senior Consultant / Web Developer, where they were responsible for the design and development of web application solutions. Their most recent role has been as a SharePoint Developer at BCF Solutions since 2016.

Gearldine Bailey obtained a Bachelor of Science degree in Computer Science from Alabama Agricultural and Mechanical University in 1985. Gearldine later completed a Master of Science degree in Computer Information Systems from the same institution in 1994. In 2010, they also obtained a certification in Information Technology Infrastructure Library (ITIL) V3 Foundation.