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Randy Vail has a diverse work experience spanning several industries. Randy started their career at OppenheimerFunds as a Service Associate and later worked as a Commodity Specialist. Randy then joined KeyBank as a Relationship Manager before transitioning to Primary Residential Mortgage as a Mortgage Loan Officer. Randy then moved to Vanguard, where they held multiple roles including Sales Administrator, Investment Specialist, Relationship Manager, and Internal Regional Consultant. Currently, they are employed as the Regional Vice President of Sales at Vestwell.

Randy Vail obtained a Bachelor's degree in Business and Economics from Randolph-Macon College, where they studied from 2003 to 2007. In 2006, they briefly attended Wroxton College, but did not obtain a degree or specialize in any field of study. Additionally, they hold certifications in Qualified 401(k) Administrator (QKA) from the American Society of Pension Professionals and Actuaries, as well as Series 63 & 7 from FINRA.