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Reggy Monsanto has diverse work experience in various roles and industries. Reggy started their career in 1997 as a Network employee at Palm Coast Data. Reggy then worked at the City of Palm Coast, where they served as a Communications Administrator from October 2006 to October 2010, and later as an IT Operations Manager from October 2010 to June 2015. Reggy then joined PDA Florida in 2013 as Vice President, managing the operations of a youth soccer club until July 2017.

In 2014, Reggy started working at Flagler Palm Coast High School, initially as an Assistant Coach for the boys soccer team. Reggy eventually became the Head Coach, leading the team to several achievements, including winning the District Championship and the 5 Star Conference Championship.

From June 2015 to May 2022, Reggy was employed at OnSolve as the IT Manager of Production Operations. In this role, they established a 24x7 NOC, implemented processes, documentation, and incident response protocols. Reggy was also responsible for budget management, vendor relations, and uptime/downtime reporting.

Most recently, in June 2022, Reggy joined Skillable as the Systems Support Manager, further expanding their expertise in the field.Overall, Reggy Monsanto has proven experience in IT operations management, coaching, and youth soccer club management.

Reggy Monsanto completed their high school education at Cathedral Prep from 1979 to 1982. Reggy then pursued a Bachelor of Arts degree in Sociology at Queens College from 1983 to 1991. In addition, they obtained an Associate's degree in Business Administration and Management, General from Five Towns College, where they studied from 1986 to 1987.