Oh yes, I forgot one last shot in the dark, a favorite travel briefcase of extraordinary quality/form/function.
Well Gabrielle, there is one supplier I <ahem> left out by accident. They came to mind as I stumbled across their website whilst googling for a leather messenger bag for my Macbook and digital camera, cell, etc. wwwsaddlebackleather.com just may be your ticket. I call your attention to the 3 sizes of leather Briefcase with a delicately expandable base, does so diplomatically, without pretense, with total class/form/function. (D-rings front and back, thus, one may control (if necessary) the width of the 9" expansion--leather thong or strap, etc.) A class act all the way around the globe.
They also offer a Thin Briefcase in two sizes that equally may be of interest; however the full Briefcase is a jaw dropper. Soon, I will be on the list for a medium size--plenty of room. If I were you I would look at the medium or large. Yes, $500+ but it's a once in a lifetime purchase (and you will quickly see why)...since your CEO will no doubt see it, be impressed enough to inquire its source, remember you forever as a class act.
Check it out. Worth a look. Should easily meet TSA standards.
Spare no expense for a once in a lifetime experience, I always say...