While this had its funny moments, I feel that (I'm gonna sound like an ass for saying this) everything that was done here was only done better in the Game Damage pilot (and no, not just because Yahtzee was in it). I know that Game Damage is quite unrelated, but I'm just using it as an example to compare this with. Even though Game Damage (in its pilot episode) wasn't a show entirely dedicated to skits, it did feature some skits, and I felt that they were executed slightly better than what I've seen here; same style of humour, but just funnier.
Don't get me wrong, I like what I've seen here, but perhaps it's necessary to examine other game-themed/related skits and figure out what exactly made them great.
All that aside, this pilot isn't bad - it isn't even sub-par - so perhaps it just needs to be given some time to find its feet.