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Randall Underwood has extensive experience in the banking industry, with their earliest position at Webster County National Bank in 1974, where they served as Senior Vice President & Cashier until 1988. Randall then moved on to Tygarts Valley National Bank, where they held the position of President & CEO from 1988 to 1992. After that, they joined Community Bank & Trust of Randolph County as President & CEO from 1992 to 1997. Following their time there, they became a Vice President at Huntington National Bank, where they remained for 18 years, from 1997 to 2015. Lastly, they joined Clear Mountain Bank, where they held the role of Senior Vice President from 2015 to 2016, before being promoted to Chief Banking Officer in September 2016.

Randall Underwood attended the ABA Stonier Graduate School of Banking. However, no specific details regarding the duration of their enrollment, the degree acquired, or the field of study chosen are mentioned.