Rat Bastard, the penultimate project manager.
Having spent years in IT, I have had experience with a ton of “characters”, this one was meant to be the epitome of a manipulative project manager type. Face was based a bit off of a fairly famous actor, but I think I changed it enough that I won’t get in too much trouble over it. Thought was to eventually come up with an illustrated “children’s book” of “Best” practices for projects.
Possibly a card game related to it as well.
First I started out with a lining up references for faces I thought would fit the need. Then consolidated them into a single image. and put that into a folder (scanned) for later reference.