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Helenka Shy has a diverse work experience spanning multiple roles and industries. Helenka began their career at Gap Inc./Banana Republic as a General Manager, where they achieved operational, service, and fiscal objectives across area stores. Helenka also worked on a long-term project at the San Francisco headquarters while managing a store in Washington, D.C. After leaving Gap Inc., Helenka worked as a Store Manager at Roots and DSW. In 2012, they took on the role of a Stay-at-Home Parent for the Shy Household before transitioning into the non-profit sector. Helenka joined the Jewish Federation of Greater MetroWest NJ as an Administrative Assistant, eventually moving up to become a Marketing Specialist and Digital Marketing Strategist. Currently, Helenka serves as the Director of Digital Marketing Strategy at the organization.

Helenka Shy's education history includes attending George Mason University and the University of Virginia, but no specific degree or field of study is provided.