Winston began his career in the disabilities field in 1992 where he worked for The Center For Disabilities. During his 18 years there, he held many positions including Residential Counselor, a Skills Specialist, Physical Therapist/ Occupational Therapist assistant, Residential Habilitation Counselor, and  tutoring at the After-school Treatment Center. Winston took online Special Education courses at Tompkins Cortland College and The University At Albany.

Winston moved to Iowa in 2009 from New York. In 2009 Winston, worked as a Shift Facilitator at New Horizons for 5 years. He joined the Discovery Living Team in as an Associate Coordinator, then in 2017, oversaw two homes and in 2019, became a Community Living Coordinator.

Winston volunteers his time to support the Salvation Army.