DevOps is a relatively new paradigm introduced in 2008 that aimed to break down the barrier between developers and ops engineers. However, the role as a DevOps has evolved drastically as the area matures. Presently, DevOps emphasizes the importance of being a jack-of-all-trades, while considering development, operations and business stakeholders. As a computer science or engineering student you may learn the theoretical aspects of computing and algorithm design that lends itself nicely towards a career in software engineering. However there is a gap left in education about operations, that is, networking, highly available and distributed systems, database design and administration. It is a daunting task to teach a student these wide breadth of skills. We would like to provide some insight from the students perspective as to how to make the transition enjoyable for both parties. In this talk we will address the challenges of on-boarding, training, mentoring, managing and promoting DevOps to students in general. We will further discuss the types of skills that will help students to bridge the gap from classroom to their first job.