It was probably just Steam bugging out. Have you levelled up again since? You may get it next time.
Actually it doesn't work like that.
I was "farming" Caravan Master, the second-to-last achievement on my list, for about a hour or so. So I get up to 30, no achievement, so I quicksave... silly mistake. That basically made me do the games all over again.. which was about 17 wins. This is because I opened the console before I started playing. Even if you reload the game, and do another win / level / etc... the achievement is only registers if you got it then and there, not afterwards. I.E. Caravan Master didn't appear after I restarted the game and got my 31th win.
Edit: @OP: Your best bet is to reload a save before level 20, and level up again. You probably hit a bad time to be disconnected for a moment.