Oliver Wendell Tyler (Jeffrey Jones), otherwise known as Skip, is a former United States Navy officer who was forced to retire from active service after losing one of his legs in an accident. Rather than leave the military altogether, he takes up a teaching position at the United States Naval Academy in Maryland, where he acts as an instructor to recruits hoping to become officers. He also serves as a consultant, providing his opinion and expertise when called upon.
In both the movie and the novel, Jack Ryan works with Skip to determine what makes the Red October special. The instructor is able to work out that it's housing a new drive system that would provide almost silent propulsion. This assessment proves essential in allowing Ryan to determine that Ramius intends to defect. However, Skip's role diverges at this point depending on whether you're reading the book or watching the movie. In the film, that's pretty much it for Skip. In the novel, though, he's a far more important character, coming up with a plan to help get the Americans in contact with the Red October and for Ryan to get on board. Later, Skip comes up with another plan to fool the Russians into thinking Ramius has been killed and the submarine sunk so the Navy can recover it safely.