With the rapid increase in online education enrollments, the need for experienced and skilled online instructors has also increased. Research confirms that novice online instructors encounter barriers to high-quality teaching, including a lack of pedagogical knowledge, skills, and low self-efficacy. Providing training and mentoring within the real-life classroom settings that novice instructors will teach, may increase novice instructors' technical and pedagogical skills, teaching confidence (i.e., self-efficacy), and transfer of training to independent teaching. In this manuscript, the authors present a design case of an online mentoring professional development program in an authentic and real-life context to improve new online instructors' pedagogical skills and self-efficacy for real-world transfer. To date, the mentoring program has graduated 13 mentees, with one currently still in the program. Of the 13 instructors who completed the program, 12 are currently teaching regularly for the online program.