Despite what Trupanion is an incredibly weak company with upper management that only promotes sycophants while overlooking the actual hard workers and talent. Especially on the marketing side, I saw a disgusting amount of "restructurings" that took place literally every time an exec was promoted or when growth stagnated due to the C-suite repeatedly shutting down ideas that didn't come from themselves. So many excellent workers with incredible ideas just flushed down the drain. Multiple times, I saw them lay off people who were literally doing the work of what would be entire departments at any other job. Trupanion advertises a good culture upfront, but the reality is that they're the exact corporate nightmare that nobody wants to be caught dead in. Don't waste your time with this one. As we all used to joke, if you're actually good enough at your job, you'll either wind up quitting in frustration or getting laid off eventually.
Oh, and very few people ever make it to that five-year sabbatical they promise. It's just a way to lure you in. The executives have a nasty pattern of getting rid of people when they're about a year out from it so they don't have to pay it out.