[3] As a young teenager, Benjamin began his working experience as a door-to-door salesman for the Miami Herald.

In 2010, Benjamin was appointed as a Traffic Hearing Officer with the 11th Judicial Circuit Court of Miami-Dade County, Florida; he has also been appointed Special Magistrate for municipalities throughout S. Florida as well as an arbitrator and mediator for the Financial Industry Regulatory Agency (FINRA).

In his community, Benjamin has served on several committees and boards such as: Florida's Local Advocacy Council, Miami Garden's Nuisance Abatement Board, Miami-Dade County's Citizen's Independent Transportation Trust, Parks and Recreation, Small Business/Minority Certification and the Human Rights Commission, Dade Public School' s Small Business/Minority Certifications, Attendance & Boundary Committee and the Save Our Future Advisory Committee.

In 2020, Benjamin defeated Ulysses Harvard in the Democratic primary for District 107 in the Florida House of Representatives.

In 2022, Benjamin defeated Wancito Francis in the Democratic primary for District 107 in the Florida House of Representatives.