In my experience it's best to focus on new user on-boarding and the needs of the most engaged "in love" users. Reasons for focusing on smooth on-board are obvio

In my experience it's best to focus on new user on-boarding and the needs of the most engaged "in love" users. Reasons for focusing on smooth on-board are obvious. Reasons for focusing on your engaged users: - It's easier to get direct and indirect (metrics) feedback that you need to actually improve their experience. - These are the users who push your product in areas you possibly hadn't considered or prioritized and can often have sub-optimal experiences. - Large teams using your product is one of the few viral channels available to B2B saas. People change jobs and say "you know, at my last place we used..." - You can probably grow their ARPU. You should definitely track people who deactivate or never log-in, but it's a hard thing to optimize.