We use Workramp for formal trainings - so we can see with that tool completion rates and if there are quizzes or assesments, how folks did on those. We have more informal training sessions called Scoops for our sales / csm team and then a Technical Scoop for our technical teams. We also hold office hours for newer, more technical product or feature releases. The overall questions and engagement - while more qualitative - help us assess how well enablement is going there.
You have several products with release dates next to each other and limited resources, so what do you do? Here’s how you can think of this: first, identify the releases with the highest ‘tier’ or ‘priority’ (classification of release tiers vary company by company). The highest priority feature is typically the one with the highest impact in the market and that should get more enablement focus.
There are a lot of messaging frameworks out there to choose from, but I take a bottom up approach: I start with the differentiators and proof points and then build my elevator pitch, value prop statements and long descriptions from those foundational components. I also use the rule of 3 for my differentiators and proof points. If you find yourself with a laundry list of differentiators or proof points, start looking for similiarities among those components to create larger "buckets" so that your audience has an easier time remembering your message.
These are all interrelated.
Messaging: Includes value propositions, your story, and pitch. Also includes things like naming, alternatives, and taglines.
Value Proposition: These are the top benefits you want to focus on for your product based on customer and competitive unput
Pitch & Story: These should be the same. Your pitch about the world before your product, the current approach, why it’s bad, the business consequences, and the new world with your product should tell a story. This story should hit on your main messaging points and value propositions.
Hope that helps!