Having worked with transportation "tech" companies in the past, even some that were wildly profitable - I've always found their execs or founders to be cold and generally out of touch with what their employees actually want.

I actually found a role here on HN for one of these companies, they'd actually built some really cool elixir tech to automate some big accounting and lending problems in freight factoring - however, they also bragged about "enabling the midwest" but in reality clearly just liked that they could run a sales team for next to nothing. One of the founders made big public announcements when they basically fired people who were "no longer a good fit" but whom had strong relationships with the rest of the company... it was weird. Also the only gig I had were they begged me to crosspost linkedin posts etc... Glad I left shortly after.