Context: I’m a co-founder at a B staged startup and not sure how broadly this applies.
Our employees ask their manager for approval before they submit an expense request. If it’s less than a few hundred dollars a year and clearly aids their productivity, the answer is yes 99% of the time.
It’s important that the product bills yearly, because our system (Ramp) has no support for recurring reimbursements.
So: long trial, yearly billing and price <$300 is best.