I came to the same conclusion. It is possible he may have worked there around the same time. My hunch is that he may have been in some sort of technical position and had access to the merchantile login while in that capacity.
His brother is in IT and has connections to the same person (and may have worked there too).
I'm not sure what value there'd be to contacting pirate's previous employers. With the exception of his younger brother, his family seems fairly stable and unlikely to up and disappear even if Trendon does.
It would be hard to just get up and leave as he has a wife with twins. I assume the twins are not his but from his wife's first husband.