In this particular case, while I knew there were gaps, I underestimated how a small (but quickly-growing) organization could mask these failures. This was often due to miscommunication, but to be sure there were people who actively obscured the ways the system was failing workers because they question the norms of tech industry benefits. This kind of risk will increase hugely in the industry as the tech execs become more pointedly anti-worker in the Musk Twitter era.