Pros
FIRE’s mission is at the center of the culture war, and it's a critical war to win. The flexible work schedule, good healthcare coverage, and 403b match are solid.
Cons
FIRE is far too top-heavy and disproportionately rewards seniority. It pays salaries to some that are much too inflated in proportion to the value they bring to the organization simply because they have been at FIRE for many years. This hamstrings the organization's ability (or willingness) to seek, retain, and fairly compensate mid-level talent. It also discourages non-senior level staff from remaining with the organization due to the lack of meaningful opportunities for growth either financially or professionally. Such a peculiar strategy has caused a noticeable trend in turnover. Despite insisting that there is no budget to compensate mid-level staff near the national average for their roles, FIRE embarked on an unsustainable hiring campaign (of mostly frivolous administrative support positions) that doubled the staff over the course of a year. The organization is constantly letting talented folks with impressive credentials walk. I've seen several mission-aligned people with Ivy League degrees leave due to unfair compensation (the directors of policy reform, government relations, and litigation were paid less than the former HR woman). You’ll spin your wheels for a couple years, get irritated at the compensation, and then they’ll burn and churn by bringing in a recent graduate. Rinse and repeat. There is also an identity crisis at FIRE. Although anybody with enough brain power to blow their nose can see that the VAST majority of censorship is directed against conservatives, the organization is going to great lengths to cater to Leftists both in terms of branding and fundraising. They abandoned the fight against grooming and indoctrination in K-12 education despite the fact that it is the area of most need. This, among other things, has forced any conservative voices out of the organization and out of its leadership as FIRE continues its leftward grift. Lastly, the organization will not win in any meaningful sense due to its approach (policy reform, litigation, individual defense). It’s not simply enough to have a "watchdog" that puts out fires willy-nilly. There needs to be institutional pressure that disincentivizes those who commit censorship from doing so. Even if your defense is perfect, you will still lose the match if you don’t have an offense that scores any points, and I don’t know any honest observer who thinks that the state of free expression is better today than it was ten years ago.