Stretching back to the ancient Greek Olympics, athletes have sought the mentorship of coaches as a means of improving their athletic ability. This tactic of seeking guidance from a master craftsman is still present in all fields from medicine to fitness. What has changed are the channels available to distribute those lessons. Modern advances in technology have made coaching simpler, convenient, and effective for people to receive world-class coaching regardless of the physical distance between them and their coach. This chapter will examine three topics. First, we will explore the benefits of having a coach guide you towards your sport or health and wellness goals. Next, we will investigate recent advancements in technology allowing coaches to reach more people while keeping them engaged and maintaining retention. We will then examine medical technology companies currently employing these strategies and how the success they are having with clients is transferable to the sport industry. Coaching has been around for millennia, what is new is how we use technology to improve the coach and client connection.