Sky Ninja Executive

He was the from the Land of the Sky who led the an airstrike on Konoha.

Personality
From what little was seen, he was the only Sky ninja that didn't underestimate his opponent and did not laugh when Konoha gives the illusion of only sending Sai to counter attack their assault.

Appearance
He had grey-brown eyes, flat brown hair and a mole near his left eye. He wore the standard Sky shinobi outfit complete with forehead protector, mask, sandals and flak jacket.

Abilities
While little is seen of his abilities, the fact that he was in charge of the many shinobi attacking Konohagakure, points towards outstanding leadership qualities as well as strategic insight. As a Sky shinobi, it also stands to reason that he had good chakra control, being capable of moulding it into mist, which enabled him to fly using the Winged Mechanical Device.

Plot Overview
He was first seen in one of the Sky ninja aircraft carrier sailing in the sea, giving the order to launch the assault on Konoha. He was seen later, coming back from the attack, warned by a Sky ninja that a Konoha intruder is in the vicinity and he send a four-man pursuit team after Sai. After the small troop was defeated, the captain continued to send troops but Sai easily dispatches them. Once Shikamaru's plan reaches its next phase, he and Kakashi show up next to Sai and reveal themselves from hiding. The captain then ordered his men to stop the attack on them and focus on the preparations for another air raid, with the intent of defeating the three Konoha ninja when the army sets out to destroy Konoha once and for all. Unfortunately for the Sky brigade, Shino had sneaked on board of their ships, as per Shikamaru's plan, and released his insects to destroy the aircraft carriers and the Sky ninja. The captain was seized with despair and incomprehension as his subordinates panicked and were sent plummeting into the sea. He then saw, to his horror, the insects devouring the ship and causing damage to their structure, and then he was killed by the collapsing ship.

Quotes

 * (About Konoha Shinobi) "I'll take you on again some other time. When we destroy the Leaf, that is!"