1) Pure startup chaos. Although Generation is a six-year old organization, the day-to-day is more like you'd find at a one or two-year old organization. Systems and processes are nowhere near where they should be, teams don't communicate well, and many staff don't have a clue about the big picture.
2) Lots of people have been placed into roles that they're not qualified for. Generation does a good job of trying to retain talent as re-orgs happen every 6-12 months. The flip side is that a lot of staff don't seem happy in their roles (ones they were not hired for) or are in over their heads.
3) Reckless growth trajectory. The CEO made "ambitious" promises to attract a massive funder that the organization does not seem capable of delivering on. Instead of focusing on program quality before scaling, Generation has promised to enroll an unrealistic, ever-increasing number of students each year. While ambition is great, the numbers aren't realistic in the context of how many people enroll in bootcamps across the country and how many competitors there are. Eventually donors are going to notice and pull funding.
4) Weird culture. Lots of Jesus talk in a secular nonprofit. There's a culture of toxic positivity across the organization that makes asking even simple questions risky. Just a weird place all around.