"We must've been through hundreds of books already and we can't find him anywhere —"
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The Head of Ravenclaw is a Professor at Hogwarts School of Witchcraft and Wizardry who has the duty of looking after and punishing the students of their House, Ravenclaw. The Head of House also serves as a Professor of a subject. Most of the heads of Ravenclaw house attended Hogwarts and were in Ravenclaw such as Filius Flitwick, who was also the Charms Master at Hogwarts. It is unknown how a professor would be elected for the post, but it's most likely that the headmaster chooses the professor who embodies all the qualities Rowena Ravenclaw valued (intelligence, wisdom, and wit) and like said above, was probably in Ravenclaw House when he/she was at Hogwarts. The first Head of Ravenclaw House was the famous co-Headmistress Rowena Ravenclaw, one of the founders of Hogwarts and the house itself alike. It's last known Head was Filius Flitwick, and no Ravenclaw students are known to have returned to Hogwarts, and thusly, the next Head of Ravenclaw House is yet to be revealed.