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Sheena Bailey has a diverse work experience history. Sheena started their career as a Software Engineer and Project Manager at University College London in 1996. Here, they gained experience in coding and project management, working on various bespoke systems. Sheena then moved on to EDS Group in 2000, where they started as a Project Manager and was later promoted to the role of Solution Centre Manager. In this role, they led a team of 40 staff members in delivering Life Assurance applications for clients. In 2004, they joined WBT Systems as the Vice President of Services & Enterprise Solutions. During their time there, they played a key role in the company's rapid growth, expanding the services and enterprise division and quadrupling services revenue. In 2006, WBT Systems was successfully sold to Avnet Inc. After that, Sheena worked at Houghton Mifflin Harcourt from 2010 to 2014, serving as the Director of Program Strategy and Delivery. In this role, they oversaw the replacement of learning and assessment platforms for consumer and K12 markets. Sheena's most recent role is as the CEO of TestReach, a SaaS platform that specializes in high-stakes exam delivery, invigilation, and support.

Sheena Bailey attended Trinity College Dublin from 1987 to 1991, where they earned a Bachelor of Arts degree in Business Studies.