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Debra Connolly began their career in 1982 as a New Store Development employee at Limited Brands. In 1986, they joined KLS Retail Services Inc. as Director of Finance. In this role, they were responsible for all financial reporting, designing and developing a computer system, directing the accounting staff, and providing staff and employee computer training. In 2000, they moved to TaikiUSA Inc. where they took on the role of Director of Finance and Administration.

Debra Connolly holds an Associate of Arts and Sciences (A.A.S.) from the Fashion Institute of Technology in Merchandising and Buying Operations, as well as a Bachelor of Applied Science (B.A.Sc.) from St Peters College in Marketing/Marketing Management, General.