I've worked at Segment.com for the last ~2.5 years. We've had an unlimited vacation policy ever since I joined, and I take 4-6 weeks off annually. Our only poli

I've worked at Segment.com for the last ~2.5 years. We've had an unlimited vacation policy ever since I joined, and I take 4-6 weeks off annually. Our only policy that I'm aware of is to keep your team posted and not leave gaping holes while OOO. Frankly, I really like it this way. I would not like to go back to tracking vacation/sick days, check-in/out times, WFH, etc. I appreciate the mutual trust the team has that people will work hard while in the office and stay away enough to sustainably enjoy life and remain productive. I'll add that I only think this sort of arrangement works if there is strong trust and leadership is a top-down role model in taking off time responsibly. I've never been asked to take time off, and I don't know that anyone has, but I've also never been asked not to. That said, I can also see this not working if you're shy about asking for things that aren't explicitly handed to you, then this system may not work as well. I'd be curious if anyone here has felt that way? :)