I think there's a similar question above on measuring KPIs. Please refer to it. But essentially I'll look at 2 parts
1. Whether sales has received the information
2. Whether sales has activated post the training which might take longer
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.
Create a quiz or set up role playing for your sales team on their understanding of the product features, capabilities and messaging. When you set aside time to observe how your sales teams are understanding and consuming your sales enablement, you create a better relationship with the team, and know which reps may need more help in what areas. By watching how well the reps could talk through the key messages in a role play, or through their quiz answers, I know what was working and what wasn’t.
This is challenging indeed and something I've had to deal with at every company I've worked for. What I've fund helps keep me and the business teams sain is to plan to launch features 14 days after the official planned released date. This makes product nervous most of the time, but most of the time they're also delayed so it all works out in the end.
I know that this is sometimes an incredible challenge. I think the challenge specifically is around balance.
A balance between: What are metrics indicative of your business / GTM goals? AND What you can control?
This requires leadership buy-in from multiple groups — ideally they would understand Marketing and Product Marketing (this is not always the case!)
Based on Your Goals, I would then identify metrics. Some examples below:
As an industry marketer I am mostly concerned around the sales cycle, ASP, win rate, content performance, and rep productivity. Good enablement, marketing, and content, should shorten sales cycles and drive how things are leveraged ie case studies, whitepapers, solution briefs, and blogs.
Often times good enablement will measure these variables continuously on a rolling basis and will work closely with industry and product marketers in understanding training gaps.
Goes back to the shared goals - which at a high level, are hard to argue with - revenue, cost savings, customer success, etc. Once you get that common agreement, then it's about the strategy / the "how" to get there. If there are disagreements here, I would start with trying to understand why and seeing it from both of their vantage points. Then trying to see if you can get them 1:1 to understand the other point of view or better yet, get them to talk to each other. Ultimately though if all that doesn't work, you may need to get a tie breaker that's someone else and who they will listen to.
In my opinion the effectiveness of sales enablement should be measured by reducing the customer acquisition costs over time and reducing the time it takes to close a deal. Having these in-process KPIs that you can track month over month will help you demonstrate how your enablement activities are helping sellers meet their quotas.