I don't have any real complaints that aren't normal to any other startup at this size. People have naturally complained that work-life balance is terrible and that your unlimited vacation/work from home is a lie. They're right, and I wouldn't recommend someone in their late-career to join the company who's looking to leverage their experience only. The issue is this is perfectly par for course for any startup you work at that will achieve the scale of Datarobot. Startups have death rates around 60% per year, and of the hundreds of companies that started in the cohort when Datarobot did, few remain. This leaves it in a select few group of technology companies that face the problems they are seeing. Technical debt is real, scope creep is real, and you'll easily feel motion sickness from the amount of times you'll pivot on a project. Want help? Too bad. The companies who solved these problems are the FAANGs, Ubers, Salesforce, etc., but those engineers have no incentive to leave those companies and join this one. You end up with problems that you have never seen, which have no known solutions that you can research, many of which only have an answer that requires a large up front time commitment. There is really no substitute for sacrifice here, and it's very easy to get tired of it and burn out. With new companies starting every day that don't have the problems, it's natural to lose steam and want to work somewhere else with far easier problems, possibly even for a raise. Of course though, if you know startups, they'll have these problems later too. This is just how startups are different from established businesses in industries that have been around for hundreds of years.
This company at this size, needs real solutions for problems that exist, and if you're up for the challenge, you'll learn a lot and certainly leave with a sense that you left far better than when you came in.
