Literacy and numeracy are identified as necessary skills for employment. QuickSmart Online (QSO) was developed with the aim of closing the gap in numeracy skills to enable the unemployed to break the cycle of long-term unemployment. QSO focuses on the learner developing fast and accurate basic skills, which in turn develops their neural pathways, allowing the learner’s working memory to be freed up to enable further learning. This paper focuses on researching facilitator stories based on feedback from learners and teachers, and on observations of QSO usage. These stories report on the learner experience during the initial development of QSO. The program was informally trialed for a period of twelve months with learners, ranging in age from eight to the late fifties, from a variety of different learning institutions. There was some evidence of engagement with the program. The five main aspects of the program that impacted on this engagement: learner confidence, learner support, learner e-literacy, online environment style, and context of learning are described. Key recommendations to increase learner engagement for the next iteration of QSO are outlined.