Of course we don't - Jared is why some workplaces don't suck. Having a dev with enough seniority to force management to do logical things is an incredible asset.
Of course Jared didn't document anything and made themselves a bus factor. Real success is when Jared makes themself replaceable because hiding detail and making yourself critical is the best way to take a site down when you're on holiday and prevent other team members stepping in and taking ownership.
You’ve turned this into a catch 22. If there were no female characters, you could argue that’s sexist. If the idiotic boss was female, you could argue all of the dumb characters are female so that’s sexist. If Jarod were the only female, that would be sexist.
How does this sketch get rewritten in such a way that it is not casually sexist?
Good point. I guess you're right, there are no flattering roles. But each of those options you list would have been less on top of existing prejudices.
Making her the (non-technical) project manager whose only contribution is "how many story points is that?", who's then silenced because "this is important!", confirms the typical prejudices about women in tech:
no technical expertise
is not in charge
does not have anything to say that is worth listening to in times of crisis
Especially being talked over. This matches many women's experiences in men-dominated environments to a T.
I'd much rather the technically competent, important but socially weird engineer (Jared) be the woman, or the incompetent boss, who's in charge and calls the shots. Even having no women in the skit would be better than this Cindy role.
Or, weird idea I know, multiple people with different roles being women. 🙄