Agreed.
I do think it's better to publish good ideas on an imperfect site than not to share at all, but yeah, every article needs to have a date on it. Leaving it undated doesn't make it "evergreen", it just makes it annoyingly cut off from the implicit context of the point in time.
Agree about the date. Even saying the year is better than nothing.
In another of his articles he begins with "Stripe recently refreshed their website..." but we have no way of knowing what "recent" means. The article might be 10 years old. For someone focused on attention to detail, he has neglected the importance of date in context:
Sometimes it's okay not to mention date, such as a movie or book review. We know it was written some time after the book or movie was released - a date already known to reader.