Not a ton of diversity, particularly in leadership. And no particular diversity trainings or focus in the day-to-day
Leadership is just not strong. Some people are simply leading areas of the business because they were there early on, but don't actually have a POV on their function and are unable to lead, motivate, and guide a team.
There's the distant vision of "automating people's financial lives" but we haven't even defined what "automation" means. What are things users should control vs. we take care of? Those sorts of things are core to the product so should've been answered or at least be on the radar to be answered, but the team is just unable to focus on some of these core questions.
Similarly, sometimes people drink their own Kool Aid too much. We don't like to compare ourselves to certain traditional financial solutions out there because that's not a great story for investors or PR even though our products overlap a lot with theirs. The team needs to be realistic about what the product actually does and where it actually fits in the landscape at least when it comes to internal discussions and not try so pretend to be something fancier than what we really are that we ignore reality.
Really hard to get things done because of lack of process and role definition. No process for roadmapping or OKRs or anything. It's just very haphazard. The company is at a size where at least some of these things need to be clear.
A lot of foundational things wrong with the product that keeps it from moving forward because always need to double back and fix something.