Hi @Derek.
Can you see a plus button in the top-right corner? What you have to do is just add a second video, minimum, and add a shortcode like this in your post/ page.
[jwp-video n=”1,2″]
Useful links
https://ilghera.com/support/topic/jw-player-7-wordpress-shortcode-options/
Playlist shortcode with JW Player 7 for WordPress – Premium 1.2.0
