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7 Answers
It's ALL about company culture. If senior people and your direct managers are taking significant time off and vocalizing it, then it's likely genuine. If everyone seems to be working constantly and vacation is frowned upon or difficult to schedule, then 'unlimited' is just a way for the company to avoid paying out accrued PTO when you leave. Ask current employees during the interview process (if you can) how much vacation they realistically take.
In finance, results often speak louder than 'face time,' even remotely. If you're hitting your targets and your work is impeccable, taking reasonable vacation should be fine. However, 'unlimited' can create ambiguity. Some people feel guilty taking 'too much.' I prefer a generous fixed amount so everyone knows where they stand. With unlimited, you always wonder what the unspoken limit is. It can lead to people taking *less*.
The main benefit to the company is often that they don't have to carry accrued vacation liability on their books. That's a financial win for them. For employees, it really is a mixed bag. I personally felt more pressure to not take 'too much' under an unlimited policy than when I had a set number of days I knew I was entitled to.
One red flag is if there's no clear process or encouragement for *planning* vacation. If it's always a last-minute scramble to get coverage, that's bad. A good sign is if they have minimum vacation policies (e.g., 'everyone takes at least 3 weeks'). This shows they're serious about well-being.
My current remote finance job has it, and it's great. But our whole team, including directors, takes noticeable holidays. We plan coverage meticulously. It's not a free-for-all, but it's respected. The key is if your performance metrics are clear and you meet them, vacation is not an issue. Some people still only take 2-3 weeks, others push for 4-5 if they plan well.
For remote roles, there's also the risk that because you *can* technically work from anywhere, the line between vacation and 'working vacation' gets blurred. You need to be disciplined about truly disconnecting. The lack of a physical office to 'leave' can make this harder with unlimited PTO since you don't see others packing up for their holidays.
I've seen it work well in some fintechs that have a very modern, trust-based culture. But in more traditional finance environments, even if they offer it, the underlying pressure to always be available might undermine the policy. The 'always on' mentality is strong in finance. Ask about average hours, weekend work expectations too.
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