In the past I've done "pilot" groups for about 1 month, then did overall enablement sessions on team all-hands. That way I could have a few of the pilot members hop on for 1-2 mins and talk about their experience with the platform. Seemed to make a big difference!
+1 to everything Lauren said as well. Additional thought, the more documentation you have, the better. To accompany my enablement sessions, I have a built-out Confluence (or your equivalent) page with ALL info, gong recordings, examples, etc.