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Cheryl McKenna began their work experience in 2004 as Vice President at AmeriTier, where they worked until 2014. In 2013, they joined Merchant Advocate as Business Development Director, where they ensure clients have the best processing agreement in place with their credit card processor. Since 2016, Cheryl has been serving as President at Such & Such, Incorporated.

Cheryl McKenna has a Bachelor's degree in International Relations and Affairs with a focus on Economics from the University of Colorado Boulder. Cheryl also studied International Affairs at the same institution. However, specific start and end years for their education are not provided.