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Roland B. has a diverse work experience spanning various industries and roles. Roland began working as a Sales Director at ADP in 2005 and held this position until 2009. From 2008 to 2010, they worked as an Account Executive at Valiant Software Solutions. Roland then moved on to become the Director of Regional Sales at EPAY Systems from 2010 to 2012, followed by the role of Director of Business Development at Clear Vision Information Systems from 2012 to 2014. In 2014, they joined National Credit Center as the Director of the Legal Department. Additionally, Roland was involved in the sports industry, working as a Racer/Runner/Athlete for Spartan Race, Inc. from 2012 to 2021 and as the Head Coach for a girls fastpitch softball team at USA Softball from 2015 to 2019. Roland also briefly worked as an Off-Ice Official at the National Hockey League in 2017.

Roland B. has attended the University of Phoenix, where they pursued studies in Business. Additionally, Roland B. also attended Bishop Montgomery for an unspecified period of time, without completing a degree or specifying a field of study.