Pros
Working in the Data org at Stitch Fix feels like being on an Olympic team. Most of my co-workers are exceptionally bright and it's refreshing to collaborate with such passionate, intelligent and experienced folks. The work environment is super relaxed and I've made some of the best work friends I've ever had at Stitch Fix. There's very little process and red tape, so you're empowered to work on basically whatever you want. The company is young enough still that there's a lot of opportunity to have a huge impact and drive projects. The pay is not quite as good as it is at a FANG company, but it's nothing to sneeze at.
Cons
Lack of process has led to various systemic problems in the org. There is very little accountability for managers, and the org structure is very tall, so half the department is either a director or manager. There is no track for ICs to progress, so there is a lot of organizational pressure for ICs to become managers. Combine the lack of accountability with the organizational pressure, and you end up with a lot of mediocre and inexperienced managers. This can be a very frustrating environment for senior level ICs. All ICs report to the lowest levels of management, since ICs don't have titles. There's no process for skip-levels, there's no performance reviews, formal OKRs, none of that, so there is no objective way to measure anyone's performance. This has lead to a very political and cliquey culture, wherein who you know determines what projects and opportunities you are given, not your actual performance. It's very unclear what things are required to be promoted, and the department seems to prefer hiring from outside rather than growing and mentoring their existing employees. There's no culture of mentorship, so it's a good place to work for a while, but your career will stall out eventually unless you've managed to make friends in high places. With so little process, it's very difficult to coordinate projects that require more than one or two people. This limits the scope of the technology we're able to build, and has also led to multiple teams solving the same problem in different ways. The leadership lacks vision and does not drive projects, so it's basically a free for all with everyone working on their pet projects, and some people do well and some don't.