I began with quick loose sketches to determine a direction. The initial logo was a flat orange shape that slightly resembled a robot. Since they really wanted this mascot to have some personality I felt that going in an anthropomorphic direction was the best course. The initial design included a full head and body with the thought that it could be animated at a later time.
One of the elements that I felt were key to selling his "personality" was a big mustache. Though I was inspired by the movie the Iron Giant for this design, I decided to go fairly flat for the initial submission.
After the selection process ended I was notified that my submission was selected with a few changes. The clients wanted to go with just a floating head. Since they were going to use it not only as their mascot but also as their main logo. Their other requirement was that they wanted the eyes to have pupils (it looked too intimidating without them they thought).
From there I started iterating again and finally ended up on this design. I knew that if it was going to just be the head they wanted I would need to up the elements to help sell the personality. I decided to add eyebrows and simple eyelids to aid me when I designed the expressions later.
I felt that having the eyebrows be able to change the overall silhouette would make the logo look dynamic and give it tons of extra character while everything else stayed fairly static.