First, you can expand or reduce the number of recent items shown in a jump list. (howtogeek.com)
Of course, there are a few more recent items I've held back that I hope to get out in the coming days, so I hope you'll look forward to that. (themmnetwork.com)
Secondly, make sure your work experience is in chronological order, with the most recent item at the top. (whatis.mba)