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Sterling Crabb has a diverse work experience, starting in 2014 at OTR Solutions as an Account Manager and later moving up to become a Senior Account Manager. In 2018, Crabb transitioned to the role of Operations Manager before eventually becoming a Sales Manager in 2019. Their most recent role at OTR Solutions is as the Area Vice President Of Sales, which began in January 2022 and is ongoing. Prior to joining OTR Solutions, Crabb held a position as Vp Of Operations at Alabama Management Society from January 2013 to September 2013. In addition, in 2013 Crabb worked as an Intern at Kohl's Department Stores Center for Retailing Excellence from May to August.

Sterling Crabb obtained a Bachelor's degree from The University of Alabama from 2009 to 2013. The specific field of study pursued during this period is unknown.