While I received some positive feedback, the general consensus was that the track came across a bit too modern and dark, and not jazzy enough for the style of the game. In short, it felt too "Brock Samson Smash (Venture Bros)" and not enough "Rusty and Danny Ocean (Ocean's Eleven)". I created another version with some horn parts sketched in, but it felt a bit forced so I went back to the drawing board.
In the next round I shifted my focus to music that had more of a straight jazz feel. I took more influences from the likes of Lalo Schifrin, Mal Waldron, and of course, Yoko Kanno. As it turns out, having an awesome name is like 80% of writing really great music. Forget studying theory/orchestration/sound design/etc. From now on I will be known as Bif LeStrange.
I decided to go with a more identifiable melody - something that even amateur burglars could hum to themselves while cracking safes at home. I kept the plucked strings and glockenspiel from the first demo, but pushed them into the background and used the falling line in the glock to paraphrase the melody played in the saxophones. I slowed the tempo down quite a bit so that I could add a bit more rhythmic density. Protip: Hand drums always make jazz cooler, and when in doubt, add more shakers! Taking cues from the epically named composers above, I let a funky bass line drive the piece. The overall effect was the following demo: