Online student success is determined by several factors, including learning effectiveness, access (academic, technical, and administrative support), faculty satisfaction, and student satisfaction. These factors are part of the Online Learning Consortium’s Pillars of Quality Online Education, which were established to ensure all students are provided a quality education, with high levels of student engagement, instructor feedback and interaction, and experiential learning opportunities. Using Teaching Assistants (TAs) in the virtual classroom is not a traditional practice for most online institutions, but is a strategy that can have a positive impact on these factors. This exploratory research study discusses a TA program that was developed, implemented, and evaluated over 3 years. Fifteen (n = 15) doctoral students were hired to provide teaching support to high-risk courses in the undergraduate programs. Background, recruitment, onboarding, division of course responsibilities, data, and outcomes of the 3-year TA programs are discussed in alignment with the five pillars. Findings suggest the addition of TAs in online education is a potentially useful strategy to improve student learning outcomes, scale, access, and faculty and student satisfaction.