This chapter first briefly discusses the expected learning outcomes (i.e., skills and competencies) in entrepreneurship education, including creativity, innovation, industry-specific knowledge, decision-making, risk-taking, problem-solving, leadership qualities, ethics, and social responsibility. Next, the chapter examines whether the conventional entrepreneurial curriculum successfully contributes to the academic and social goals and meets the needs and expectations of students and society at large. It also presents a discussion on why the recent socio-cultural, technological, pandemic-related changes, including mass digitalization, working remotely or working from home, asynchronicity and global communities of practice, demand new approaches to enhance learners’ experience and maximize the achievement of learning outcomes in post-secondary entrepreneurship education. Then the chapter explores artificial intelligence (AI), such as the virtual classroom, AI Tutor, interactive smart boards, augmented reality (AR), virtual reality (VR), simulation, and big data systems, as a disruptive technology in education. While computer systems with ‘intelligence’ are already performing many tasks that were commonly associated with humans, there are growing interests, concerns and uncertainty regarding the wider application of AI in education. Accordingly, the chapter includes a discussion on the trends in AI adoption in education and how AI is likely to reshape curriculums, teaching and assessment, as well as its positive and negative impacts on teaching and learning. Further, this chapter explores the enormous potential of AI specifically in entrepreneurship education. A rich discussion is presented on the possibilities and conditions for an effective instructor-AI collaboration that can make an important contribution to all the key areas of teaching and learning in entrepreneurship education, such as the curriculum, instruction, assessment and feedback. An instructor-AI collaboration has the potential to improve curriculums, pedagogical practices, learner motivation and engagement, which are critical to achieving learning outcomes. The chapter concludes with the argument that while integrating AI in entrepreneurship education is capital intensive, it is worth investing in instructor-AI collaboration as it facilitates the progress of learners by providing them with customized learning support without unduly limiting individual choice.