"Unlimited vacation time" isn't always a red flag. I work for a company with unlimited vacation time (Braintree) and I've always felt comfortable taking vacatio

"Unlimited vacation time" isn't always a red flag. I work for a company with unlimited vacation time (Braintree) and I've always felt comfortable taking vacations. In fact, in June I went to Europe for over 3 weeks, and I still feel comfortable taking time off for the holidays as well. A "real" unlimited vacation policy is a strong positive signal about the company. It shows that (a) people are trusted to manage their own time and not to abuse the system and (b) the people who work there are good enough and driven enough to deserve that trust.