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Bobby Osborne has a diverse work experience spanning multiple industries. Bobby started their career as a Student Intern at St. Joseph's Hospital and Medical Center in 2010. Bobby then moved on to work at Wegmans Food Markets as a Produce Customer Service representative from 2005 to 2011. In 2011, Bobby joined Enterprise Rent-A-Car as an Assistant Branch Manager/Branch Corporate Account Manager, where they played a key role in increasing branch revenue and vehicle fleet size.

In 2013, Bobby joined Empower Federal Credit Union and held various positions over the years. Bobby started as a Member Service Representative and then progressed to the role of Branch Supervisor, where they led a team and oversaw the training of merger staff. Bobby then served as a Branch Manager, where they managed a team and led projects for the company. Bobby later became the Deposit Operations Manager, responsible for building and implementing new processes and procedures. Bobby then transitioned to the role of Deposit Systems Manager, where they established a new department focused on project-related functions for the retail group. Finally, Bobby currently holds the position of Vice President of Digital Services at Empower Federal Credit Union.

Bobby Osborne attended the University at Buffalo School of Management, The State University of New York from 2008 to 2012. Bobby earned a Bachelor of Science degree in Business Administration with a concentration in Finance. In November 2019, Bobby obtained the Certified Credit Union Financial Counselor (CCUFC) certification from the Credit Union National Association. Bobby also has additional certifications as a Medallion Certified and a New York State Notary Public, although the specific institutions and dates of obtaining these certifications are not provided.