I do not know how much of an unpopular opinion this is (nor do I know how much of a canonical basis this take has), but I think that when you analyse Lili and Holly’s dynamic, although there is *definitely* an element of internalized sexism that paints Holly’s perception of her coworker (she calls her a bimbo, for god’s sake), there is also, I think, the issue of class that pops up.
Holly isn’t living in poverty, but you do get a sense that she is working class — she’s got a one room apartment that is a fair distance from the economic center in which she works, she’s not spending a lot of money on non-necessities, etc. Similarly, both of her parents worked hard throughout Holly’s childhood to make ends meet, and when Holly’s mother passes, it’s not in the lap of luxury — it’s in a pretty bare bones (though still adequate) hospice situation.
On the other hand, Lili comes from old money. Like, there isn’t even a human equivalent to the kind of social position which Lili occupies — she is the descendant (albeit distant) of one of the most important cultural figures in Haven, and although we don’t know much about her family’s current standing, it is mentioned that her name carries a lot of weight.
Although I don’t think Lili explicitly said, “give me a job in the LEP because of my family name”, I think Holly might look at the hardships that peppered her life as opposed to what she knows of Lili’s life, and feel an extraordinary sense of bitterness. I do headcanon that Lili is a lot smarter than Holly gives her credit for, but even if that weren’t the case, I think it’s certainly an indication of where the LEP is at that Holly feels having a woman coworker who is just… average is unfair. Even if Lili did coast into her job on the virtue of her name alone, there are plenty of men with whom Holly works that are “just average” — it’s not truly progress if the only class of women that are allowed to enter the workforce are the cream of the crop, whereas the competence of men in said workforce runs the gamut. With Holly’s men coworkers, you have the high, high achievers (e.g. Trouble, Root, etc), and then you have the more average group (e.g. Grub, Chix, etc). Hell, you even have the “terrible at their job group” (e.g. Sool)!
I think it would be interesting to have a look into Lili’s own perspective on her role in the LEP, what privileges her name affords her, and the difference perhaps in how she navigates womanhood due to her location in Haven’s haute-monde.