Stripe has already existed for a while, and has gone through ups and downs. There was a period where customer experience was first, and the systems inside were built fast and in rather cavalier ways (See Greg Brockman famously telling everyone in a MongoDB convention about using Mongo's oplog as a queue). There were times where internal tools teams could spend all the time they needed to get about as much shine internally as the external facing websites were. Huge investments in everything. But there's just so much churn, as some staff burns out, and others realize that they have so much vested stock that continuing in such a high intensity environment is pointless, that whatever Stripe might have been during your tenure might be very different from other people's, and you can both be right.