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Gayle Webster has worked in various roles since 1997. Gayle began their career as a Social Worker at the Cuyahoga County Division of Children and Family Services. In 2015, they became a Voluntary Intern at CMSD Cleveland. In 2017, they joined VERDTEK as a Technical Support Specialist and later became the Technical Support Manager, managing a total of 20 member desk and supporting over 3,000 clients. In this role, they coordinated with stakeholders, support staff and management team members for the The WIC program, for the purposes of improving Dynamics software that services over 800,000 participants.

Gayle Webster completed a Bachelor's of Art in Sociology/Psychology from Hiram College in 1996. Gayle then went on to obtain a Master's Degree in Information Systems Management from Keller Graduate School of Management in 2011.