Office 365 Update Rings

That sounds like a sensible approach and is in line with the best practices:

"Deploy the Semi-Annual Channel (Targeted) to a targeted group of representative users who can pilot new features of Office. The users should include people from business groups across the organization and their client devices should include the architectures in your organization (32-bit and 64-bit), as well as any critical line-of-business applications, add-ins, and macros."

Have a way of communicating this to pilot users, making this an active exercise with the following expectations

• Use the release notes, which are really good with info on feature updates with lots of links like here
• Focus on the March and September Semi-Annual Channel (Targeted) releases 
• Introduce pilot users to new features through the appropriate comms, a Yammer community I think could work well
• Empower pilot users, they have the opportunity to try out new features four months ahead of everyone else but they have to know what to look out for and how to flag potential bugs or other issues
• Get feedback, perhaps a questionnaire June and November, ask about specific features and any productivity benefits that you can apply to the whole organisation

As part of this, I'd have a much smaller group including yourself on the monthly channel so you have an even earlier opportunity to prepare and be able to signpost new features.