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Winda Caraballo has a strong background in human resources, with experience in various leadership roles. Winda began their career as a Human Resources Director at Citifinancial in 2001, managing the department's functions such as employment, wages, benefits, training, and employee relations. Winda later joined Doral Bank as an AVP, Human Resources Business Partner, and continued to excel in managing human resources activities. In 2011, Caraballo worked as a Human Resources Director at Consolidated Waste Services, overseeing the department's responsibilities until 2013. Afterward, they joined Sears Holdings Corporation as a Regional Human Resources Director before joining Sheraton Puerto Rico Hotel & Casino in 2015 to be the Human Resources Director. In this role, their major responsibilities included budget administration, managing expenses, and overseeing various areas such as employment, training, labor relations, and payroll.

Winda Caraballo's education history includes a Master's Degree in Labor Relations from the Universidad Interamericana de PR. Prior to that, they obtained a Bachelor of Business Administration (BBA) with a focus on Human Resources Management/Personnel Administration, General from the Universidad de Puerto Rico. Specific start and end years for these degrees are not provided.