While the significance of employment for individual well-being and sense of belonging is well-documented in the literature, individuals with autism spectrum disorder (ASD) face substantial challenges in securing and retaining meaningful employment after completing their schooling. This chapter addresses the gap in research concerning employment readiness, access, and retention for individuals with ASD by exploring the potential of generative artificial intelligence (GAI), specifically ChatGPT, to support their transition from education to employment. The chapter evaluates three propositions: ChatGPT as a tool for communication and social skills training, as a source of just-in-time (JIT) information, and as a support resource for caregivers. Based on a synthesis of existing literature, this chapter highlights the unique advantages of GAI, such as providing a low-stakes environment for practicing social interactions and delivering immediate, reliable information, while also emphasizing the need to integrate AI alongside professional guidance in order to maximize effectiveness.