While I wouldn't necessarily say any of that is a red flag it does all fall into what I think you called the "maturity level" of the whole org. So are you ther

While I wouldn't necessarily say any of that is a red flag it does all fall into what I think you called the "maturity level" of the whole org. So are you there to help build the maturity level of the whole org or is it something you can contribute to and assist others in developing? It sounds like you have a sense for such things. Working on the company's pre-IPO maturity could be a huge win for stakeholders like yourself ( or could land yourself solidly on the side of the stakeholders ). On the other hand, if the assumptions you operate on depend on the maturity of other systems - no sense in building up their K8s helm if all they have now is Windows Server pets - then you might find it very hard to pull the direction you thought you were brought onboard to work toward. Regard the place the same as they'll regard you. Make a list ( not on their computer ) of things you see, file under Good | Meh | Bad, and track for BIG RED FLAGS until your 90-day point. If you make it to 90 with no BIG RED FLAGS, and the data leans positive, then you have a list of things to work on. Otherwise, line up some interviews.