Aaron Levie's outsized conviction when building Box
Despite no investors other than Josh Stein and Mamoon Hamid coming in, Aaron and Dylan (<25 yrs at the time, never worked in a company, didn't complete college) never went on-prem, gave up millions in revenue for a decade. That kept their architecture cloud-first. Many of the customers that had passed on them and are now customers.
Developer tools (Atlassian model) are one instance where you can sell software in a self-service way/ over the phone. Every other CIO/CISO wants to meet in person, shake a hand.