Affirm

Supportive and equitable culture, great people, and empathetic leadership. The benefits are awesome, salary is competitive, and my manager was one of the best I've ever had.

Operating in high levels of ambiguity is definitely a given here, but so is a high level of autonomy and the option of developing your career in whatever direction you want to carve out for yourself.

I really enjoyed working there and was gutted when I was one of the 19% impacted by layoffs.

Pervasive technical debt, lack of a global presence, and information overload. Affirm err on the side of more information being better than less. Normally, I'd agree with this philosophy, but the volume of email and notifications is incredibly hard to manage, even with the use of filters and automation. It's very easy to miss something important unless you allow your inbox to overflow with information.

Even a seasoned individual contributor can struggle with doing good work when given basically no operational guidelines or answers. One of my tasks, for example, was to develop a partnership contract framework with the legal team. After months of struggling to get any feedback from senior management on what we should and shouldn't agree to, we based it largely on certain existing live agreements. Shortly after they were signed, we finally received feedback that we overcommitted.