Role-play is an active learning tool that increases the involvement, motivation, and responsibility of students through their immersion in the very industry for which they are learning and preparing and has been used in a wide range of settings, including education, business, and entertainment, to facilitate education, problem-solving, and personal growth. As such, role-play was implemented in an Introduction to Esport course to help students better understand and experience the real-life planning, obligations, and execution of the many roles and responsibilities necessary to host and stream an esport competition. In this manuscript, we offer an overview of student experiences and provide lessons learned to help enhance future role-playing and experiential learning opportunities in the esport space. Results from this project demonstrated that role-play can be an effective pedagogical tool, affording students with opportunities to enhance their knowledge and familiarity with the esport industry, learn and practice industry-specific skills, and experience a real-time event competition requiring them to apply what they learned in the classroom.