serato softwere

Yes you should update to the latest Serato version.
The latest version will have a feature called “autoplay” on a button below the crates (left lower side), when you engage autoplay it will continue to play through your playlist and auto-transition songs.
But as I said you will need to go to Serato.com and get the latest version. Maybe also check out the tutorial video on their site to see whats new.