After a successful 18-year career in radio, Gaither finished his MS in Computer Information Systems from Boston University and began working in Charlotte County, Florida as an HMIS Data Analyst for the Homeless Coalition. In less than a year, Gaither was promoted to CTO and restructured the entire Homeless Management Information System (HMIS) and streamlined all technologies at the organization. Gaither also led the technology side of the COAD initiative that provided COVID financial relief, scheduled COVID testing, and scheduled COVID vaccinations, through an online portal. Gaither left to create Gaither Dynamic, a data dashboard company, consult on various projects such as building racial equity dashboards, creating replacements for the VI-SPDAT, and contributing to an HMIS LMS. Gaither also travels the country speaking on human services and technology related topics such as data visualizations, dashboards, and preventing and ending homelessness in the United States.