Jake is never seen without some kind of form of headwear as he usually is seen with his toboggan, helmet, hat, or construction headwear.
Due to his role in rescuing other snowboarders on Jake's Mountain, Jake is effectively the resort's Ski Patroller in addition to being the Resort's owner/proprietor. After the events of "The New Pup", Everest begins living on Jake's Mountain and helps Jake out with rescuing snowboarders.
This effectively makes Jake & Everest the resort's Ski Patrol and local mountain rescue team (as the PAW Patrol is based in Adventure Bay acts as the emergency rescue services for the whole of Adventure Bay) and helps take some of the burden off Ryder and the PAW Patrol, as they can rescue snowboarders/skiers more quickly when they get into trouble on the mountain, only calling on the PAW Patrol when additional help is needed.
Being a fellow rescuer and close bond with Everest, Jake could be considered an unofficial honorary human member of PAW Patrol. Jake is among the handful of humans who assist the PAW Patrol during an emergency or situation, along with Katie, Alex Porter, Mr. Porter, and Ace Sorensen.