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John Underwood, Jr. has extensive work experience in the advertising industry. John started their career in 1989 at American Express as a Public Affairs Officer & Collections at the Optima Card Retail Operations Center. In 1991, they joined Tinsley Advertising as an Account Executive, where they worked until 1996. During this time, they also served as an Account Manager at Young & Rubicam from 1996 to 1998. In 1998, John returned to Tinsley Advertising and held various roles, including Executive Vice President, Account Management Supervisor, Chief Executive Officer, and Chief Executive Officer/Owner. John is currently the CEO/Owner of Tinsley Advertising, a position they have held since November 2020.

John Underwood, Jr. attended the University of North Florida from 1987 to 1991. John pursued a Bachelor of Arts degree in Marketing/Marketing Management, General, which they successfully completed.