I think the concept is good and it really gets you thinking, but I don’t think Carl is likeable enough. Even if he gets nice at the end (script not finished at the point of reading) he is not a character i want to follow over a whole Episode or even whole Seasons. Let’s say you don’t want him to be nice because in your logline you explicitly wrote "Jerk". That’s totally fine but I think he needs some Character trait that makes him likeable or gets the audience more invested. The relationship between Carl and Stephanie is great, I especially love the part where he insults her mother and she is sitting right next to him. Jokes like that really got me, the humor of his former employees is funny too, but Carl is more mean than funny (but humor is subjective, so I respect that). I would recommend keeping the jokes in the same type of style, meaning you should choose between dry or dark humor. I think the conversations between the characters are well written and interesting. But I would recommend sometimes to be subtler like when saying to the grandma that she is old. In that situation it maybe even funnier if you let Stephanie insult her with a funny joke about how old she is. Again, my favorite conversations where between Carl and Steph, I just love there dynamic and how Stephanie sees through all the bullshit and jokes. I am not sure what the main conflict is…Because I don’t really see how the story goes from here. I mean Carl is a jerk with money and without and now that he won the lottery will become even meaner? Or does he try to get back with Stephanie with his new acquired wealth? Your scripted was really finished so maybe there will be a big conflict or maybe someone tries to steal his money. The pacing overall was okay, the beginning was very slow, but the story picks up the paste after that although the part where he actually wins could have had more build up. On the other Hand, you could say that is intentionally done because of the quick and large amount of money the lottery winner gets is kind a sudden too. To summarize my thoughts, I think Carl needs a major Character change, it is okay to make you character an asshole but we as an Audience need to be invested in him to even want to follow his live and just winning the lottery isn’t enough for that. I love Stephanie as a Character being the personification of his lost life.