The Boss Guy is a Blue Penguin that works in the Ski Lodge with Boss Lady and the Guard. He and Boss Lady kept many penguins in the lodge, leaving the dead ones in a corner. He might know about the Mutant Penguins due to them being kept up in the Attic of the Lodge.
In The Reward, he, Boss Lady, and the Guard met Lil Jeffy as he ran into their tent. He and Boss Lady realized it was Lil Jeffy and gave him a warm welcome, with Boss Guy thanking Lil Jeffy for killing the rest of the gangs and making their lives easier. As they began to make a deal with Lil Jeffy, though, Boss Guy took notice of Lil Jeffy's simple nature and began to suspect that he might be an imposter. He asked Lil Jeffy to prove his identity, and in response Lil Jeffy raised his arms up to strike the pose that "killed" The Gang Leaders in The Leaders, which confused Boss Guy and Boss Lady. They began to think that Lil Jeffy might be crazy, but then the tent lifted up and flew away. This was actually caused by the puffles inside Floppy Green Penguin due to the Agent being scared of the Mutant Penguins. As far as the Boss Penguins knew, though, Lil Jeffy had telekinetically flung the tent away with his powers, and this was enough to convince them that he was the real deal. Then the Guard told them that their pizza was ready outside. Boss Guy, Boss Lady, the Guard, and Lil Jeffy headed down to the Ski Village. Then the Guard whacked Lil Jeffy unconscious with a Hockey Stick, and the group headed up the Ski Hill.
In The Gathering, he accompanied Boss Lady as she explained their deal to the Sledder Gang. As she explained, he helpfully pointed out that they had been planning to hand Lil Jeffy to them as a sign of peace until they saw how destructive Lil Jeffy can be. All seemed to go well for him until Businesmoose and The Cannibal appeared, with Businessmoose trying to talk to Lil Jeffy. Then three Strangers and Problem Solver appeared, demanding the Boss Penguins to hand over Lil Jeffy. Soon Scavenger and Big Jeff arrived, also wanting to take Lil Jeffy; at this point Boss Guy was moved to ask why so many penguins were showing up. Soon, Floppy Green Penguin, Agent, Orange Puffle, and the penguins from the Lodge arrived in time to see everyone else fighting over Lil Jeffy. Boss Lady then initiated a gang war by striking a new deal with the Sledder Gang: if they could get rid of all the other intruders, Lil Jeffy would be theirs. During the fight, Boss Guy tried to fight one of the Strangers, but he was shoved into the sled Lil_Jeffy was tied to. He then stood and watched from a distance as the other penguins fought until Big Jeff got ahold of the sled, at which point everyone stopped fighting to watch what he'd do next. Big Jeff then slid down the hill on Lil Jeffy's sled, and Boss Lady yells at the Sledder Gang to go after them.
Unlike Boss Lady, the Boss Guy remains the same attitude throughout his appearance so far, he hasn't shown any signs of anger, rather the same old emotions of curiosity, confusion, and a calm behavior. He is likely the "good cop" of the Boss Penguins.