"You know, if you go back eight years or something, the Evernote architecture made all the sense in the world!" Going forward, the team needs to continually invest in solving its tech debt problems, rather than papering over them to build something new.

We did something unconventional on the inside, and then we matched it with an unconventional communication strategy, which was to just go out like in my first few months and say, "Right. Here's the state of the world: The app's kind of broken, we're going to fix it, it's going to take a while." As you go through the process, being transparent bring... See more