When logging into Outreach, users are prompted to select their role and continue connecting their mailbox and calendar even after they have already been set up.
New Outreach Users
Make sure users are accessing their account via outreach.io instead of outreach.io/onboarding. If the onboarding link is bookmarked, remove the bookmark and navigate to outreach.io and bookmark that address.
New users bookmarking the outreach.io/onboarding link and accessing their account through there.