I agreed with David on who is requesting the document. I would think about the buyer journey and the sales process, and ask myself would the leave-behinds or one-pagers move the funnel? I would also confirm my hypothesis with multiple sales reps at different levels of performance. Usually, if there is a problem, it will showcase itself across a wide section of the sales team. I would apply the same methodology to a CS team.
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.
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:
Your CMS (content management system) should have some sort of archiving parameters in place that should remind the PMM team when things get stale.
With that said, all the reminders in the world won't matter if people ignore them, so I recommend you also have a "librarian" of sorts manage your content site - whether it's in a sales portal or in another tool, someone who is in charge of managing the site, tracking metrics, and also monitoring / organizing PMM when content needs to be refreshed/archived.