I’ve never won, but entered two, so…
Personally, I don’t think winning should necessarily be your goal. If winning is all you want to think about, then you do you, but I think that these contests are more about being creative, having fun, and interacting with new people. For example, I haven’t won either contest that I entered, but I’m still so happy that I entered because I made new friends and learned new things.
But in a technical sense, the key to “doing well” is reader retention. It’s described everywhere basically if you look on the contest threads or other threads floating around the forums asking about reader retention. In a nutshell, it’s “how many people read” AND “do they keep reading.”
The Episode panel also reads your story, too, so it helps if you check their rubrics on the contest threads and check their guidelines.
Again, it shouldn’t be more about winning, but rather the experience. Hope this helped 