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Rob Frost began their work experience in 1990 as an Assistant Vice President at Merrill Lynch. Rob then moved on to Dun & Bradstreet in 1999, where they worked as a Senior Financial Analyst until 2002. In the same year, they joined Community Bank System as the Director of Financial Planning & Analysis, eventually becoming the Vice President of Finance and Director of Financial Planning & Analysis in 2015.

Rob Frost earned their Bachelor of Science degree in Finance and Financial Management Services from SUNY at Albany, where they studied from 1984 to 1988. Rob later pursued their MBA in Finance at NYU Stern School of Business, completing their studies there from 1993 to 1997.